Charlie’s Bully Pulpit

Charlie Sykes the critic politicians fear, the moralizer liberals love to hate. Smart, articulate, connected, he can swing elections and reshape public policy. But beneath his media image is a complicated, isolated man, a walking contradiction.

Editor’s note: This profile of Charlie Sykes was originally published in the July 2000 Milwaukee Magazine.

It was a very good week for Charlie Sykes.

On Monday, the third day of April, ABC’s “20/20” came to town to interview him about how the busybody Census Bureau was trampling on the public’s right to privacy, a topic near and dear to Charlie – and, conveniently, the topic of his latest book.

On Tuesday, Election Day, Gov. Tommy Thompson called the studio line at WTMJ-AM to put in an (impromptu?) on-air plug for Diane Sykes, the conservative incumbent candidate to the state Supreme Court – and Charlie’s ex-wife.

Wednesday, in a post-Election Day roundup, Charlie basked in the news that his ex had absolutely stomped her challenger, Milwaukee Municipal Judge Louis Butler Jr., or “Loophole Louie,” as Charlie had branded him for days on end. Over and over, Charlie repeated the percentage spread – “65 to 35!” – and you could almost see the smirk widen across his face.

Thursday, another good day. One of Charlie’s many Democratic whipping posts, Senate Majority Leader Chuck Chvala, caved on his threat to stall a bill to renovate Lambeau Field. Charlie took aim like a 12-gauge, gleefully pelting Chvala for trying to “hold the bill hostage.”

And on Friday, though Charlie vowed to finish the week on a mellow note, he just couldn’t hold back. Following up on a Spivak & Bice column in the Milwaukee Journal Sentinel, he reamed retiring Milwaukee Common Council President John Kalwitz for his 11th-hour plan to give outgoing Ald. Wayne Frank extra retirement benefits. By mid-afternoon, the idea was stone-cold dead.

Yes, it was a good week for Charlie Sykes. For those five days in spring, Charlie was on his game, ripping everyone in sight. According to Charlie: Defeated County Supervisor Tony Czaja was a “crackhead,” Police Chief Arthur Jones was “a little dictator,” John Norquist was a “Lime duck” and George Watts a “bad loser.” The Journal Sentinel’s editorial board was “out of touch,” the Oshkosh Northwestern was a “rag,” the Census Bureau was a “bully” and Janet Reno’s Justice Department was not unlike “Nazi Germany.” John Kalwitz was a “crook,” Wayne Frank was a “deadbeat,” Louis Butler was still “Loophole Louie” and Charlie’s ex-pal, PR exec Todd Robert Murphy, who opened the door to Charlie’s broadcasting career by introducing him to Mark Belling so many years ago, was a has-been pundit whose time had come to “hang it up.”

Such is the talk show world of Charlie Sykes, a Chicken Little reality where the sky is always falling and every public figure is forever running for cover.

There is nothing mealy-mouthed about Charlie Sykes – or the reactions he generates. He is a hero to his fans. From the silver-haired ladies who flock to his book signings to the suburbanite salesmen who tie up their car phones to the stay-at-home moms with the radio set all day to WTMJ, Radio Free Charlie is a rare alternative to the “left-wing media,” a champion of tax reform, welfare reform and school choice. He’s tough on crime, he’s pro-life, he’s an honest-to-God defender of the Truth.

Listen to the gushing comments of one typical caller:

Sykes: “Gerry from Racine, you’re on 620 WTMJ.

Gerry: “Charlie, everything you say is so good and correct. We need more people like you on the radio, on the TV, on everywhere – to let us know what’s going on, to inform us of everything that’s being said.

At his best, Sykes is a shaper of public policy. With WTMJ’s 50,000-watt blowtorch at his back, he is a force to be reckoned with, capable of injecting himself into political contests and commanding the attention of the state’s most powerful. When John Norquist agreed to a mayoral candidate debate last spring, his campaign called Sykes. When George W. Bush hit the Wisconsin campaign trial, Sykes wrangled an on-air educational forum with the Texas Republican at a Milwaukee school.

Sykes has had virtually every high-ranking state politician on his program and many national figures as well – from Newt Gingrich to Hillary Clinton. He has built a reputation as a facile commentator, crossing over from Milwaukee Journal reporter to Milwaukee Magazine editor to national author to radio and TV host. He is masterful at identifying issues and institutions that strike a populist nerve: the press, government, politics, crime, race.

“He takes issues and turns them inside out, upside down, looks at them from all angles,” says Justice Diane Sykes, who speaks with her former husband nearly every day. “He comes to a conclusion he believes is right and puts it [out] in a very entertaining and compelling way. That’s his skill and strong suit. It always has been.”

Democratic insider Evan Zeppos has known Sykes for 15 years and frequently appears on his TV panel, “Sunday Insight.” “If someone were to ask me to describe Charlie, the first word 1 word use is intellectual. And if you’re an intellectual, you’re opinionated,” he says. “Other people may have a different point of view, but I think the world of him. Is he open-minded? Not yet. Is he willing to listen to other opinions? Yes. I would predict that in 10 years, Charlie will be more liberal than he is today.”

To his detractors, though, Charlie Sykes is a menacing wag, intellectually dishonest, self-serving, a race-baiting holier-than-thou media star long on complaints and short on solutions. From 8:.30 a.m. till noon five days a week, he is “the Jerry Springer of the radio waves,” as one observer calls him.

“I think he’s unfair much of the time in his approach, and wrongheaded as well,” says Mike Drew, former TV and radio critic for The Milwaukee Journal, who has kept an eye on Sykes’ broadcasting career since the very beginning in 1990. “I do think he’s terribly bright and hardworking. And I give him immense credit – both Charlie and Belling – for dragging Milwaukee radio into the 20th century. But neither provides a balance. There’s no countering message. And as a Democrat, it bugs the hell out of me.”

Indeed, it is under the skin of Democrats and liberals that Sykes frequently resides. Defining himself cleverly as “a recovering liberal,” he downplays his political influence, preferring to label himself “a libertarian, with a small l.”

But his Republican ties are undeniable. One of his oldest friends is Republican Assembly Speaker Scott Jensen, a likely candidate for governor and a regular guest on Sykes’ TV show. He’s had friendly ties for years to Gov. Thompson, who handpicked Diane Sykes in 1999 to fill a vacant chair on the state Supreme Court. Sykes’ books have earned him at least $120,000 in grants from a conservative think tank and have opened doors to Republican Party darlings such as William Bennett and Bill Kristol. Last year, Sykes was offered a three-year paid fellowship at Stanford University’s Hoover Institute to examine education policies.

Insiders estimate that Sykes makes between $125,000 and $150,000 at WTMJ. Add to that his off-air ventures and Sykes is the captain of a lucrative cottage industry of conservative opinion.

“It’s been very much to Charlie’s benefit financially to be a conservative,” says a former friend.

While he remains a man of letters – writing books, writing a monthly column for Madison’s left-leaning weekly, Isthmus, from editing a newsletter for the right-leaning Wisconsin Policy Research Institute – Charlie Sykes is best known in Milwaukee for what comes out of his mouth.

Sometimes that fire-breathing outrage is more spectacle than substance.

“People bitch at him because they think he ought to be a journalist and he’s not, he’s not trying to be, he’s given that up,” says longtime public relations man Dave Begel, who once had a local talk show himself. “Charlie understands the nature and the value of show biz. He knows what people want to talk about – that’s where his journalism skills come in. He can be a shepherd for a discussion that he doesn’t know anything about.”

But there are others who know a more manipulative Charlie Sykes, a man who, through his electronic bully pulpit, denigrates and moralizes with impunity. They see a Sykes who is one-sided, negative, hypocritical. As one observer puts it, Charlie Sykes is Milwaukee’s parent, exhorting listeners to do as he says and not as he does.

“He’s a civilized Mark Belling and therefore far more dangerous,” says Dave Berkman, media critic for WHAD-FM and the Shepherd Express Metro. “He speaks meanness without sounding mean.”

This darker side extends beyond his on-air persona, beyond his conservative message. Sykes, say some, can be vengeful, a man who burns bridges, who cannot sustain friendships.

“Retribution? That’s part of his passion,” says Jim Romenesko, former reporter for The Milwaukee Journal and Milwaukee Magazine and now a national on-line media critic. “There is very little gray area with him. It’s either black or white. Charlie is the sort of personality that, when he decides he doesn’t like you, boy, does he hate you.”

“I am afraid of him,” says one spurned friend who sees Sykes as a “spinmaster” capable of destroying careers. “He’s bright, he’s resourceful and he’s emotionless…. My best policy is to stay off that son of a bitch’s radar screen.”

Outside of the studio, away from his professional cronies, away from his books and his daily blows against the status quo, Sykes is an isolated man. Disarm him of the ax he grinds day in and day out and his many contradictions emerge. He is a man of immense talent and ambitions, yet unsure of what to do next in life, a man who has gained the respect and fear of the power elite while failing to win the long-term loyalty of even a single friend.

Everybody has a take on Charlie, and every take is different. He is a complex figure, not easy to know, not completely understood even by those who have known him most of his life.

“Charlie has gone through many metamorphoses,” says Joe Obenberger, a Chicago lawyer who has known Sykes since they were freshmen at Nicolet High School and last saw him a year ago at their 25th class reunion.

“He’s not a person at this time – he’s an ongoing enterprise. I sit here and I scratch my head: I’m Rip Van Winkle and I wake up and Charlie’s a big shit in Milwaukee. But I remember him as just Charlie.”

Like many men, Charles J. Sykes followed in the footsteps of his father, a journalist, political campaigner, author and college professor who died in 1985 at age 63. And like many men, Charlie has succeeded beyond his father’s own dreams. Jay Sykes grew up in Philadelphia and, after serving as an Army code breaker during World War II, earned a law degree from the University of Washington, where he met his Montana-born bride, Kay. Charlie was born in Seattle on November 11, 1954, and was the couple’s only child.

Bored with the law. Jay Sykes decided to go into journalism, and when Charlie was 4, the young family left Seattle as he began a series of short-lived jobs at newspapers in New York state. From kindergarten through third grade, Charlie attended a different public school each year.

In 1962, Jay Sykes was hired by the Milwaukee Sentinel-as a reporter. A few years later, he became a staff editorial writer, writing editorials consistent with the paper’s conservative stance. Away from the newspaper, though, he let his liberal opinions fly. In the late 1960s, he was elected to the board of the Wisconsin ACLU.

A short, pudgy man with an indifference toward wardrobe and a knack for getting in the last word, Jay Sykes was a maverick, an iconoclast, an issues-oriented intellectual.

“I think I ended up doing a lot of things he would’ve liked to have done,” says Charlie. “He would’ve done them better, though.”

To Charlie, his father was always “Jay,” never “Dad.”

“We would sit and talk, every issue, back and forth, talking about politics,” he says. “He was literally a contrarian. If you put him in a room with 10 people, he would find a way of disagreeing with eight of them…. It was just his personality. He was not mean, he was just kind of playful. And he just couldn’t stand pompous self-righteousness.”

The Sykes family settled into a comfortable life on a Fox Point cul-de-sac, a life Charlie likens to TV’s “The Wonder Years.” As he hit adolescence, though, the world around him began to change, from idyllic to tumultuous. Across the country, young people rallied in the streets against the Vietnam War.

Just starting Nicolet High School at the time, Charlie was a refugee from the counterculture, a freckle-faced teenager in a button-down Oxford, his thick black hair clipped short above his ears. Socially, he was on the fringe, uninterested in school clubs and organized sports.

“He wasn’t a jock, he wasn’t a stoner, he was in no crowd at all,” says Obenberger.

But from his father, Charlie developed a passion for one thing – politics.

Jay Sykes changed jobs again in 1967, quitting the Sentinel to teach journalism at the University of Wisconsin-Milwaukee. Late that year, he took the post of state campaign director for U.S. Sen. Eugene McCarthy, who was running as the peace candidate against President Lyndon Johnson.

Jay Sykes set up an office in the Wisconsin Hotel in Milwaukee. When signing up volunteers, he recruited his son. It was a heady experience for a 13-year-old.

LBJ soon dropped out of the race and Sykes went to the Democratic National Convention in Chicago, where Charlie worked as a page. Though McCarthy lost the nomination to Hubert Humphrey, “Clean Gene” remains “one of the noblest, most honorable men in American politics” to Sykes. “There has never been a political figure I liked as much as him.”

Those six months imprinted upon Sykes an idealism that is unmatched. “My whole life,” he says, “has been downhill from ’68.”

The following year, an inspired Sykes joined the Wisconsin Young Democrats as one of the youngest members ever. When he was 15, his father ran for lieutenant governor, losing to Martin Schreiber. Charlie helped out in the statewide campaign. A year later, Jay Sykes took a car trip to Washington, D.C, to research a book he was writing on U.S. Sen. William Proxmire. Again, Charlie was at his side.

In 1974, as a freshman at UWM, Charlie ran for office himself. No Democrat had come forward to challenge Republican incumbent Jim Sensenbrenner, an assemblyman from the North Shore and today a congressman from the 9th District.

But there was a catch: Sykes was pro-life, a position contrary to the Democratic platform. The Democrats funded him anyway, and running under the slogan “A Different Kind of Democrat,” he was trounced by Sensenbrenner, a surprise to no one.

But his pro-life campaign signaled a growing crack in his liberalism. And as elements within the antiwar movement became violent, he became increasingly disillusioned.

“We were starting to see a lot of people who couldn’t care less about the war,” Sykes says, looking back. “They just wanted to break stuff… It’s one thing to think that war is immoral. It’s another thing to think that America is this awful, terrible place in the world…. I sensed that liberalism, instead of this free spirit, was becoming this rigid and constant moral hectoring. Things started to change.”

Charlie’s personal life had changed as well. When he was 18, he converted to Roman Catholicism. While his mother was a Methodist and his father a non-practicing Jew, Charlie was raised without a religion. But through his college readings of poets and authors from the Oxford movement and a chance discussion with a Jesuit at Marquette University, he was drawn into the Catholic Church.

Around the same time, he joined a pro-life group, SOUL – Save Our Unwanted Lives. It was through SOUL that he met his first wife, Christine.

Christine Libbey was 18 when they met. Charlie was still living with his parents and going to college year-round, taking a ton of credits each semester.

In May 1975, Charlie and Chris were married at St. Jude’s Catholic Church in Wauwatosa. He was 20, she was 19. They moved into an apartment near Gilles Frozen Custard Drive-in. Weeks afterward, Charlie graduated from UWM summa cum laude with a degree in English. Five months after the wedding, the couple had a baby daughter.

“Charlie came down with a child pretty soon after getting married,” says his best man, Steve Chandler, who had joined the Young Democrats with Charlie, was present at his Catholic baptism and shared his conversion to neoconservatism.

The marriage lasted less than three years.

“I thought Chris was more of a family person than Charlie was,” says Chandler. “She wanted to spend a lot of time with her family. I don’t think Charlie liked that…. She was not as intellectually oriented as he was.”

Divorce records show that custody of the couple’s 2-year-old daughter went to the mother. Chris Sykes was working as a dental assistant, bringing home $120 every two weeks. Charlie made a biweekly salary of $404. When they divorced, Charlie was ordered to pay monthly child support payments of $303.

Sykes at times had difficulty making payments. Several times, he slipped into arrears; for three months in early 1980, his ex-wife went on AFDC. Sykes eventually made payments directly to his former wife, according to court documents. He gained legal custody of his daughter when she was 17.

“There was a lot going on. I’m not going to talk about back then,” Sykes says today. “But I have always supported my daughter. My daughter really spent a great deal of time with me, I paid a great number of her bills, I put her through college, I put her through private high school, all the ballet lessons, clothes, a lot of things…. Of all of the things that I am most proud of, it is the way that I have raised my children.”

Before his second marriage in 1980, Charlie was granted an annulment of his first marriage by the Catholic church. In 1982, he wrote an article for Milwaukee Magazine on the nettlesome effects that annulments can have on divorced couples and their children. Titled “Divorce, Catholic Style,” it was the first feature he wrote for the magazine. He didn’t mention a word about his own divorce and annulment.

Sykes learned the ropes of news reporting at the suburban weekly The Northeast Post. After a year in the trenches, he landed a job at The Milwaukee Journal. It was a big break and he quickly made his mark. Starting out on the North Shore beat, he soon was promoted to City Hall reporter.

His boyish, freckled-faced countenance won him the nickname “Howdy Doody” among Common Council members. But he was no one’s puppet, this brash whiz kid in blue blazer and khakis. In short order, Sykes was tangling with then-Mayor Henry Maier, who, for term after term, had regarded The Journal as his nemesis.

“To be a good reporter, you have to have a killer instinct,” says Joel McNally, former Journal reporter and columnist, whose own head-butting sessions with Maier years earlier were legendary. Sykes had that killer instinct, McNally says. “Charlie was out to get people. And he did it very well.”

During the summer of 1978, Charlie was asked by his editor to mentor a journalism student for a day while he made his rounds at City Hall. The student was Diane Schwerm, the daughter of the manager of the Village of Brown Deer and a junior at Northwestern University.

The impressed young woman went back to school that fall but returned to The Journal an intern the following summer. By late 1979, Diane and Charlie were dating. “We had this long-distance thing going,” she recalls. Soon after she graduated from college, she was hired as a reporter at The Journal.

It was love in the newsroom. By August 1980, they were married. Big changes were in store for both of them. After just a year at the paper, Diane gave up journalism and enrolled in law school at Marquette University. Charlie, meanwhile, had burned out on the City Hall beat. City magazines had become a new trend in journalism, and as a lark, he and another reporter put together a proposal to make Milwaukee Magazine a more hard-hitting publication. They submitted their proposal and forgot about it.

Nearly two years later, out of the blue, Sykes got a call from the editor of Cleveland Magazine, whose parent company had bought Milwaukee Magazine. The editor had dusted off Sykes’ proposal and offered him a job as a staff writer.

After four years as a star reporter at The Journal, Sykes made the leap. “I thought, if you can’t take a chance when you’re 27 years old, when are you gonna take a chance?”

Jim Romenesko was covering the police beat for The Journal at the time, and on Sykes’ recommendation was also lured to the magazine. “We were two guys in our 20s and really wanted to shake things up,” Romenesko says. “And we did.”

The magazine soon gained a reputation for skewering sacred cows – Sykes’ expose of Secretary of State Vel Phillips, Romenesko’s unflattering profile of Police Chief Harold Breier, a media gossip column called Pressroom Confidential, written initially by Sykes.

But the magazine struggled financially, and in late 1982 it was put on the block. When it looked as if no buyer would emerge, Sykes took a job as a reporter on Channel 12’s investigative team, without any experience at all in television.

He quit within two months.

“When you wake up one morning and you realize that your bosses are named Mickey and Bunny…” Sykes cracks, referring to Bunny Raasch and the late Mickey Hooten, Channel 12’s news director and station manager, respectively, at the time. “They wanted to have an investigative unit, but they were scared of their own shadows.”

Fortunately for Sykes, Milwaukee Magazine was purchased on the brink of death by Harry and Betty Quadracci, principal owners of Quad/Graphics and owners of the magazine today. Sykes was hired back weeks after the sale. When Editor Frank Kuznick left, Sykes was made managing editor; he was promoted to editor in January 1984.

Sykes quickly made the magazine his showcase. His writing was prickly and his politics were unpredictable, which made him an especially good writer of commentary, says Bruce Murphy, a contributing writer who was hired to the staff in 1986. Sykes would lash out at Republicans and Democrats with equal measure of scorn.

Sykes’ byline was everywhere – political columns, features, investigative articles. In one memorable cover story, “Death of a Horse,” he dissected a Mequon marital dispute in which a well-known plastic surgeon allegedly killed his ex-wife’s prized horse. And in “The Best, Brightest, Dimmest and Dullest Legislators,” he rated the state’s lawmakers, causing such consternation at the statehouse that the Madison Capital Times reprinted the article.

“Of anything he wrote, that was one that really got the buzz going,” says Romenesko, “because it was such a no-holds-barred attack against people who really deserved to be attacked.”

In 1985, Sykes asked a freelancer to write an essay about academia. The writer was his father. Jay Sykes had taken a leave from teaching at UWM to edit the Green Bay News Chronicle.

“He was always bitching about life at the university,” says Sykes. “And in a typical conversation, I said, ‘Why don’t you put your money where your mouth is? You write a story; I’ll put it in Milwaukee Magazine.’

Weeks later. Jay Sykes turned in a long, wry essay that lambasted college professors as overpaid slackers who devoted too much time to esoteric research projects and frivolous courses.

The article was published in October 1985 – posthumously.

“He brings in this story for me to run,” Charlie recalls, “and then maybe four days later he dies, suddenly, on a Friday night, here in Milwaukee. A massive heart attack. I got to the emergency room at Columbia Hospital just too late…. To say it was the worst experience of my life is putting it mildly, because I didn’t have a chance to say good-bye.”

Romenesko remembers Jay Sykes popping into the magazine from time to time. “Charlie’s dad,” he says, “was probably the closest friend he ever had – and ever will have.”

Months later, Sykes got a call from a literary agent. He had read Jay Sykes’ essay and saw it as the basis of a book. Charlie thought it over and decided that he would be the author of that book. Armed with his father’s notes, he signed a contract to write what would become Profscam: Professors and the Demise of Higher Education.

“He didn’t leave me any money or anything, that was not the legacy,” says Sykes. “The legacy was the book.”

In a column eulogizing his father, Charlie wrote: “He taught me how to ride a bike, hit a baseball and handle a tennis racquet, but being around Jay, I learned that the clash of ideas was the only competitive sport really worth pursuing.”

After four years as editor of Milwaukee Magazine, Sykes was ready to move on. He was itching to write his book, start something new – again.

Compounding his restlessness was what Sykes calls a “strained” working relationship between him and Betty Quadracci, the magazine’s associate publisher. Magazine publishing was a new field for Quadracci and she was learning all areas of the business, including the editorial process – how story ideas were developed and assigned, for instance. Sykes, meanwhile, grew territorial.

“I remember, for example, we had an editorial meeting, and Charlie was very reluctant to let Betty into that meeting,” says Romenesko. “He just thought that she was trying to encroach on editorial.”

Others on the staff at the time remember Sykes as artful and temperamental, responsive to Harry Quadracci, who he regarded as a father figure, recalls one longtime staffer, but resentful of Betty, particularly when she was promoted to president and publisher.

Another staffer recalls Charlie referring to a book he had read about bosses. The hook listed several types of managers, including one that Charlie said resembled himself – the Lone Wolf “No matter what,” read the book, “a lone wolf only does what he wants to do, in the way he wants to do it, which is usually by himself.”

Things came to a head in early 1988. Bruce Murphy and freelance writer John Pawasarat were completing an article critical of the Medical College of Wisconsin. At the time, Harry Quadracci sat on the college’s board of directors.

Sykes and Harry Quadracci had an agreement: Sykes would have complete editorial freedom but would alert Quadracci of any article that would be potentially embarrassing to the magazine’s owners.

While Quadracci had learned of the article through Murphy, he had not been informed of it by Sykes. Three weeks before the issue was scheduled to go to press, Quadracci saw a copy of the story at the magazine’s office for the first time. Still Sykes had not contacted him.

A showdown was imminent. The owner and editor met at the magazine office, and in a closed-doors discussion, Harry Quadracci fired Sykes for insubordination and for betraying his trust.

Sykes says he was blindsided. After he was fired, he wrote in a letter to the editor Isthmus that Betty – but not Harry – had been informed of the story’s progress. But others say he had been playing Betty against Harry to undermine her authority, that he had been planning to resign on the very day he was fired and go off to write his book and contribute columns to the magazine.

It didn’t work out that way.

Feeling betrayed and abandoned when no one on the staff came to his defense, Sykes took his case to the public, drumming up coverage of his dismissal in the local press. According to his version, he was fired because he had refused to knuckle under to what he saw as an attempt to censor the magazine.

“Charlie decided to make himself a cause celebre,” says Murphy. “It’s his natural tendency…. He’s a very good self-promoter.”

Today, Sykes is much more charitable toward Betty Quadracci.

“Perhaps I didn’t understand what her needs were [and] she didn’t understand what my agenda was, necessarily,” he says.

At the time, he was devastated. “For a middle-class kid to say, ‘I’ve been fired,’ is like saying, ‘I’ve been arrested and thrown in jail,'” says Mordecai Lee, a former state legislator who befriended Sykes in the 1970s. “He was really shook up…. But already in his mind he had a next step – he knew he could write the book.”

Dedicated to Jay Sykes, “author, curmudgeon, journalist, lawyer, politician, antihero, father, mentor, friend and teacher extraordinaire,” Profscam was published late in 1988 to mostly positive reviews.

But Sykes knew he couldn’t make a living on book sales alone. To pay the bills, he went to work as the public relations flack for Dave Schulz, the charismatic and controversial Milwaukee County executive.

Working in government was an “education,” says Sykes – and a mismatch. He resigned after 10 months.

It was March 1989 and suddenly he was out of work, looking to redefine himself in the same way that he – and his father – had done so many times before.

This time it was radio.

In the late 1980s, talk radio was spreading like wildfire across the country. The political landscape had changed. Republicans had held the presidency throughout the decade, and a more conservative mood prevailed. From city to city, call-in talk shows sprang up, patterned after the granddaddy of conservative talkers, Rush Limbaugh.

Sykes stepped into the red-hot medium one foot at a time, sitting in occasionally on Kathleen Dunn’s talk show when she was at WTMJ-AM.

He was a natural, fast on his feet, well-spoken and strongly opinionated.

Mark Belling had gone on the air at WISN-AM in 1989 and swiftly rose to top- rated radio host as Milwaukee’s answer to Limbaugh. Searching for local pundits for weekly panel discussions, he tapped ad man Todd Robert Murphy, a regular guest on Channel 12’s” This Week” with Dave Begel. Murphy recommended two Charlies – Charlie Dee, a liberal Milwaukee Area Technical College professor, and Charlie Sykes, whom Murphy had met when he ran Dave Schulz’ campaign.

Murphy, Dee and Sykes became Belling regulars, jawing it up about politics. And before long, Sykes began substituting tor Belling when he went on vacation.

“I had this idea Belling’s audience had to be the stereotype – a bunch of redneck, angry white guys,” remembers Sykes. “But I kept running into people who were listening to these panel shows. And they were intelligent, they were articulate individuals. I began realizing, this is an alternative medium.”

In May 1992, WISN hired Sykes to host his own show. But the station didn’t sign him to a contract, and in June 1993, he abruptly jumped ship for WTMJ, announcing on the air without notice that he was quitting WISN. He walked out of the station and never looked back.

Today, be speaks diplomatically of Belling.

“Mark and I don’t have a personal relationship, but hopefully we have a relationship of equal parts rivalry and respect,” he says. “He’ll poke me once in a while, but it doesn’t seem to have quite the barb that it used to have…. He’s made no secret that he is annoyed by the fact that I was his fill-in, then jumped to TMJ.”

Belling wouldn’t be interviewed for this article, but most media watchers credit him with launching Sykes’ broadcasting career.

“Belling sees Charlie as his creation,” says Tim Cuprisin, TV and radio critic for the Journal Sentinel. But there are vast differences between the two. Sykes is more of a player in influencing public policy through the forums and debates that he hosts.

“Belling couldn’t do that,” says Cuprisin. “Charlie’s taken more seriously.”

Part of Sykes’ status is due to WTMJ’s long-standing dominance in the market as the city’s leading AM news source, a source that station insiders say tailors its news presentation more and more to fit Sykes’ talk show message.

But so much of it is style, pure show biz. “Charlie is smart,” says Cuprisin. “He knows journalism, he knows the world is not black and white. But the Charlie who’s on the radio believes the world is black and white. So, in many ways, Charlie on the radio is playing a character. It’s a bit.”

Today, after 10 years of broadcasting, Sykes is as popular as ever, “the mayor of radio,” as he’s called by Mikel Holt, editor of the Community Journal and a regular on Sykes’ TV panel. Up against Dr. Laura Schlessinger on WISN, Sykes is holding his own in the ratings, still stepping on toes and stirring things up with his right-wing bit.

How potent is his bit? Some of Sykes’ liberal critics write him off as just a blustery voice preaching to the converted. Sykes himself downplays his influence, preferring to paint conservative talk radio as the David to the liberal media’s Goliath.

“It strikes me as highly ironic that liberals say there’s just way too much conservative ideas,” he says. “We’re still pretty much a voice in the wilderness.”

But ask those who have been on the losing end of his outrage and they’ll say his voice is loud, extreme – and very effective.

When the AIDS Resource Center of Wisconsin asked the Milwaukee County Board in 1998 to fund its needle exchange program, Sykes waged a full-tilt crusade one week before the proposal went to a vote.

“He was not only offering an opinion through the media, it was a call to political action,” says Doug Nelson, executive director of ARCW. “He was giving out the number of the County Board and encouraging listeners to call in…. We could not compete with that. We lost by a couple votes.”

When attorney Peter Earle ran last year against incumbent Milwaukee County Circuit Court Judge William Haese, Sykes attacked him as a bleeding-heart liberal who was soft on crime, sometimes blasting Earle immediately following his paid radio spots.

“It was that blatant,” says Earle, who lost to Haese by just 1.6 percentage points. “I think talk radio contributed to a one- to two-point swing.”

When Walter Kelly ran for state Supreme Court in 1997, Sykes stumped for his opponent. Justice Jon Wilcox.

“He basically gave Wilcox in excess of a quarter-million dollars of free air time,” says Kelly, a Milwaukee lawyer.

Before talk radio began hammering on Kelly, polls showed him far ahead of Wilcox. Though not as apparent at the time, the Kelly-Wilcox contest was a referendum on school choice, one of Sykes’ pet issues. Kelly was against school choice, Wilcox for it. A year after the election of Wilcox – and with the appointment of Justice David Prosser by Gov. Thompson – the high court ruled 4-2 that the Milwaukee Parental Choice Program was constitutional. If Kelly would have won, the court likely would have tied and an appeals court decision ruling the law unconstitutional would have stood.

The latest target of Sykes’ electronic campaigning was Louis Butler, who lost the state Supreme Court race to Diane Sykes.

“While I understand talk show hosts have freedom of speech,” says Butler, “I’m somewhat concerned that here he is providing free advertisements, when he has a potential financial stake in the race” – the financial well-being of his children, specifically. Had Diane Sykes lost, she would have been out of work – and a salary of $ 114,561.

Sykes ideological soul mates have no qualms about his donations of free airtime.

“Tough,” says George Mitchell, a school choice consultant who frequently appears on Sykes’ TV show. “It’s a free country and the First Amendment provides a right for people to express their opinions.”

The merger of the Sentinel and The Journal raised the profile of Sykes and talk radio, Mitchell says. Milwaukee today is a one-newspaper town with an inconsistent alternative press. Editorial pages have become predictable defenders of the status quo, he says. There is no must-read columnist. So, in the void, Sykes has become a big fish in a small pond, rising to the top as an outlet for people out of the mainstream.

Sykes uses the Journal Sentinel as a resource and a foil. He “rips and reads” from the paper every morning, using news stories as fodder for his commentary, then criticizes the paper for its editorial policies.

“If he wants to criticize us, fine. We’re the big guys and we ought to be able to take it,” says Marty Kaiser, editor of the Journal Sentinel. But “if he didn’t read the paper, the show wouldn’t exist.”

When choosing his issues, though, Sykes’ black-and-white world view makes critics see red. Seldom does he cover the complexities of issues such as healthcare or the economy. You won’t hear a show about the struggles of single parents living in a post-welfare state or the ethical dilemmas of fetal surgery. Instead, it’s hot-button issues like gun control, school prayer, affirmative action, bad laws, the liberal press.

Sykes agrees that there’s little room for nuance on talk radio. “Print is still where you develop ideas,” he says. “It sets the agenda. It always has, it always will. It’s where you can do the thoughtful work. [But] radio can disseminate those ideas more effectively because you have an intimacy with someone…. Television has the emotional power to make something vivid and real in a way that all but the very best print can’t do. You ought to be able to communicate in all of these media…. I made a specific decision that I was going to stay in electronic media for this very reason.”

But communicating ideas is one thing. When dissemination turns to preaching and demonizing, Sykes becomes but a mere propagandist.

“There is a wide gap between his intellectual facade and the fact that he is not at all interested in examining ideas or even a marketplace of ideas,” says pundit Charlie Dee, who has worked to counter Sykes’ point of view for years. “There’s absolutely no balance” other than the appearances of moderate liberals like Evan Zeppos and Assembly Minority Leader Shirley Krug.

“He has every right to be strident, I don’t hold that against him,” says Eric Von, host of a talk show on WMCS-AM.

But so many of his discussions on race relations pander to stereotypes, feeding racist perceptions that African Americans are criminals or not as smart as whites.

“If he was out in the community talking to people, [Sykes] would be informed about what’s going on,” says Von. “I don’t like senseless attacks and pointless discussions. You’re not doing the public a service, you’re just feeding your ego.”

Beholden to ratings and advertisers, commercial talk show hosts “don’t feel any compunction about bringing in the other side,” says Dunn, who today hosts a show on Wisconsin Public Radio’s WHAD-FM. “That seems to me to be irresponsible people would say that it’s more entertaining to listen to radio like that, and maybe it is. But you need to hear from different viewpoints.”

Maybe it’s the audience. Maybe listeners aren’t looking for balance or debate or enlightenment at all. Maybe they’re simply looking for someone they can agree with, someone to tell them what to think.

But even as a loud-mouthed populist, Sykes is playing a role.

“He portrays himself as a fighter against the corrupt establishment,” says Michael Rosen, chair of the economics department at MATC and local activist. “But in fact, if you look at who he represents and who he’s defending, it’s generally the most powerful and wealthy people in the state” – the Thompson administration, the Republican party, corporate Wisconsin, the Packers, the Brewers – “not the 5,000 people who lost their jobs at Briggs & Stratton.”

Sykes points out that, with the exception of the Wisconsin Right to Life Committee, he no longer does fundraisers. He stopped giving speeches for the state Republican Party two years ago.

But belying his claim of providing an independent voice are his ties to conservative think tanks, groups that through a somewhat incestuous relationship have supported his career as a writer.

Since 1992, Sykes has been paid up to $20,000 annually to edit a journal by Wisconsin Policy Research Institute, a Mequon polling firm run by like-minded conservative Jim Miller. Miller in 1986 was recruited to Wisconsin from New York by Michael Joyce, president of the Bradley Foundation, which contributes about $400,000 annually to WPRI. Joyce formerly ran the John M. Olin Foundation, a conservative think tank in New York. Joyce introduced Sykes to the Olin group, which subsequently made book grants to him through WPRI totaling at least $ 120,000: To complete A Nation of Victims, he was given $35,000; for Dumbing Down Our Kids, another $35,000; for a yet-to-be-published anthology on school reform, $50,000.

The Olin Foundation today funds the Jesse Helms Center Foundation; the Goldwater Institute; William F Buckley’s “Firing Line”; National Review magazine; the Intercollegiate Studies Institute, which arranged college book tours for Sykes; the Institute for Contemporary Studies, which underwrote a book on school choice by Mikel Holt; and the Federalist Society, whose members include Robert Bork, Kenneth Starr and Justice Diane Sykes.

Through talk radio, television, freelance columns, speaking engagements and his books, “[Sykes has] become a conservative conglomerate,” says one former friend, mouthing the agenda – while mining the bank accounts – of the conservative intelligentsia: the Hoover Institutes, the William Bennetts, the Michael Joyces.

Joyce, a Humphrey Democrat who converted to neoconservatism in the 1970s, is a friend and adviser to Sykes. He cautioned him against ghostwriting an autobiography of Newt Gingrich five years ago, and he introduced him to Bennett, Kristol and the Hoover crowd.

Sykes doesn’t fit tidily into ideological labels, despite his conservative Republican links, says Joyce. “He’s an intellectual. Thinking is both his pleasure and his work.”

And he insists that Sykes is his own man.

“The idea that I could influence such a majestic mind is incredible,” says Joyce. “He’s not Charlie McCarthy, he’s Charlie Sykes. If he’s faking it as a neo-con, my God, he’s doing a good job of it.”

On a hot August night in 1996, two Whitefish Bay police officers in Big Bay Park watched a man and woman light the fuses of three or four bottle rockets along Lake Michigan. The police confiscated a few boxes of illegal fireworks and ticketed the couple. Both were fined $55.75 for setting off illegal fireworks and warned to stay out of the park after hours.

The couple was Charlie Sykes and Janet Riordan, a 34-year-old opera singer at the time, who lived in West Bend.

The story eventually made the paper, raising eyebrows about the state of the marriage of Charlie and Diane Sykes.

Phones lit up in local newsrooms as callers reported sightings of Charlie and “another woman” – together at a Chicago hotel, at an opera in Waukesha, at a book signing.

Charlie’s actions added grist to the rumor mill. Further raising suspicions was his relationship with “Liz Wodehouse,” the phony name of an occasional guest on his radio show. That mystery woman was identified by the Journal Sentinel’s Cuprisin as Riordan.

After dodging questions about her, Sykes eventually described her as “a researcher” and “a family friend.”

The fireworks incident in particular was a real “what-were-you-thinking?” moment: a married man, a high-profile public figure setting off fireworks at night with a woman who was not his wife.

Sykes admits it was a dumb move – “I should have [the ticket] framed as my own Stupid Award” – but he refuses to discuss the incident.

Charlie and Diane Sykes were divorced on June 1, 1999. The couple issued a press release to announce the dissolution of their 19-year marriage, and the divorce file was sealed by the court at their lawyers’ requests.

“When Diane and I got divorced, we both just said very publicly that we hoped people would respect it out of the interest of our kids, who are doing extremely well,” says Sykes. “Look, I have made very human mistakes that most people make in their lives. I certainly would never suggest that my personal life should be the exemplar for everyone else. And the fact is, having failures is part of life.”

Diane Sykes and the couple’s two boys live in the gray-and-white house in Bayside that the couple once called home – picket fence in the front yard, basketball hoop off the driveway. Charlie lives in a fashionable apartment complex five minutes away – swimming pool open to guests, the interstate freeway humming below his balcony.

Diane Sykes would not discuss the couple’s breakup. But when asked whether she had expected to be married to Charlie for the rest of her life, she answered with a word: “Yes.”

Charlie Sykes is less abrasive face to face than he is on the radio. He can be very personable, self-effacing, even shy. Off the air, he’s willing to show a human side, a side not often seen or heard. Yet he is fiercely defensive of his private life. “I think that you can draw a line of privacy around you,” he argues. “The personal is the personal.”

He has lashed out at the Journal Sentinel’s Cuprisin, accusing him once of spying on him at a Little League baseball game, when Cuprisin claimed he was only watching his godson play ball. He has gone after newspaper columnists for what he saw as “personal attacks” against himself and his former wife, Diane. And he eventually shut off communication with Milwaukee Magazine for this article after the questions became too personal for his liking.

But it’s the way he conducts his personal life while criticizing the lives of others that leads critics to label him a fraud. Sykes is not above prying open the lid on the personal lives of others, public figures as well as private. If it makes good radio, he will become a moral beacon, passing judgment on the teachers’ union or welfare mothers or abortion doctors or animal rights activists, peppering his commentary with judgmental catch phrases such as “the nanny state,” “the Oprah era” and “the total breakdown of culture.”

He will harp about values and character and personal responsibility. But he’ll conveniently sweep his own foibles under the rug of privacy.

“Here’s a guy that passes himself off as Dr. Laura’s equivalent on family values and moral righteousness,” says Charlie Dee. “He’s been divorced twice” and has had a questionable relationship with another woman while married. “If this doesn’t epitomize hypocrisy, I don’t know what does.”

Sykes brushes off the comparison to national talk show host Laura Schlessinger, who has a few skeletons in her own closet.

“Just that hectoring nastiness, that is not the way you rebuild a culture,” says Sykes. “What I’ve found is, people who are my worst critics are usually the ones who listen to me the least…. They don’t understand that there’s a difference between moralizing conservatism and libertarianism. I’m not Gary Bauer. I’m not Pat Robertson.”

Dave Begel sees some of the criticisms of Sykes as professional jealousy.

“For all of us, there are things that we believe are of value,” he says. “The challenge of life is living up to those values, and we’re not always up to meeting those challenges. Does that mean we believe in those things any less? I don’t think so. Shit happens in life.”

But like politicians, a social critic at the state’s most powerful radio station should be held to higher standards, says Jerry Benjamin, chief executive officer of A-B Data, who became a friend of Sykes during the Dave Schulz days.

“Most real-life situations are filled with moral ambiguity, complex questions, with no clear line of right or wrong sometimes,” says Benjamin, a Democratic activist who has worked on campaigns for Howard Metzenbaum and John Glenn. “But when you pick up the cudgels to expose the problems of the rest of the world… criticizing the deficiencies of public officials, for example… you have to put your own on the line, too.”

Benjamin is one of several former friends of Sykes who says Sykes has a way of letting his intractable nature undermine relationships. “I’d be surprised if he maintains any long-term friendships,” says Benjamin.

Former UWM professor Walter Farrell met Sykes in 1992 when the two were regulars on Belling’s Friday afternoon round table. Their on-air differences of opinion eventually dissolved into off-air name-calling.

“Charlie had this insatiable desire to win every argument,” says Farrell, now teaching at the University of North Carolina. “He’s a competent guy, a bright guy who is very insecure. I’ve seen others like him. They cannot brook a difference of opinion because they think they’re smarter than everybody.”

It was philosophical differences that also came between Sykes and Mordecai Lee, who Sykes named as one of the best state legislators in Milwaukee Magazine in 1986.

Today, Lee is an assistant professor for governmental affairs at UWM.

In 1993, Lee had formed the Wisconsin

Coalition for Public Education, an anti-school choice group. Sykes invited him to appear on his radio show to debate a choice proponent from Washington, D.C. Lee declined, suggesting an alternate spokesman.

“The next thing I know, someone calls me and says Charlie is on the air saying that I’m a chicken for not doing the debate on his show,” says Lee. He called Sykes and they agreed to have lunch. But the next day, Sykes left a voice-mail message for Lee, canceling their meeting.

“That was the end of our friendship,” says Lee. “I can only conclude that he decided our friendship counted less than scoring points on the air.”

Sykes says he has a busy professional and family life, too busy for friendships. But maybe burning bridges has become the cost of his work. This past January, he spent an hour on his show talking about friendships. It was an uncharacteristically personal show for Sykes, dark and confessional.

“I’m not looking for sympathy here,” he told a caller. “But if that was the measurement – that a friend had to be someone you’d disclose intimate details of your life to – and we were describing being a male friend, I’d have to say I don’t have one.

“I developed friends early on professionally, a lot of really good friends. One of the unfortunate things, though, is – and here’s the difference between liberals and conservatives: Conservatives think liberals are wrong about ideas. Liberals think that conservatives are bad people. And it never occurred to me… that if I disagreed with them that we couldn’t be friends.”

Todd Robert Murphy doesn’t buy Sykes’ explanation. “The friendships that have dissolved have nothing to do with his politics,” says Murphy, a moderate Republican who once called himself a friend of Sykes. “No one cares what Charlie’s politics are. This is Charlie playing the victim.” His tendency. Murphy says, is ending personal relationships abruptly and permanently – “like an emotional guillotine.”

No one knows Charlie Sykes in the same way. He’s seen as a liberal-turned-conservative-libertarian, wary of the GOP – and a buddy to Wisconsin’s top Republicans.

He’s a nationally recognized author who hobnobs with conservative intellectuals – and an AM talk radio “squawker” with a talent for show business.

He’s a devout Catholic and prolife volunteer – and a moralizer who has twice divorced.

He’s a well-connected insider who moves easily in circles of power – and a man without friends.

“Charlie’s a walking contradiction,” says Isthmus News Editor Bill Lueders, who has known Sykes since the Milwaukee Magazine days and now edits Sykes’ monthly column in Isthmus.  “He certainly is a good writer, researcher…. But more often than not, I find his columns objectionable. He’s kind of a conservative hack”

Then Lueders reconsiders.

“No, he’s not a hack,” he says. “A truer label would be a contrarian. He wants to stir things up, he wants to put in his two cents…. he’s a contrarian.”

Contrarian. It’s the same word Charlie uses to describe his father.

Move for move, Charlie has matched his father’s varied professional life. Like his father, he’s run for office and worked for a politician. Like his father, he’s edited a publication, written commentary, authored books. Charlie even taught journalism for a brief time at UWM.

But Sykes hit a professional peak early, reaching more goals than most people do in a lifetime. And now, at age 45, he’s not sure what comes next – or what he’s looking for.

Two years ago, Sykes gave his fans and WTMJ a scare when rumors began to circulate that he was leaving the station. He took a leave of absence to complete his privacy book – and, it was said, to put his personal life in order – and when he returned to his show, his ratings rocketed.

But Sykes’ current contract with WI’MJ expires at the end of the year. He doesn’t say he’ll sign on again. He doesn’t say he won’t.

His 10 years as a radio talker is the longest gig Sykes has had, and he hints that he’s getting restless.

“I’ve never denied that I have a relatively short attention span,” he says.

But what would he do next? How would he remake himself yet again?

His next book will be “a less important book,” he says, though he won’t discuss topics. He would love a researcher-in-residence position at the Hoover Institute, but he’d have to leave behind his show and, more importantly, his kids. And he admits out loud that he’d jump at the chance to write a regular column for a daily newspaper – yes, even the Journal Sentinel – though no offers have been made.

So where does he go from here?

“My father always used to say, ‘I’m trying to figure out what I want to be when I grow up.’ And he would say this when he was 50. At a certain point, you do wonder what you want to do. It’s an immensely difficult issue for me.”

Not even Charlie has the answer.



Kurt Chandler began working at Milwaukee Magazine in 1998 as a senior editor, writing investigative articles, profiles, narratives and commentaries. He was editor in chief from August 2013-November 2015. An award-winning writer, Chandler has worked as a newspaper reporter, magazine writer, editor and author. He has been published in a number of metro newspapers and magazines, from The New York Times, San Francisco Chronicle and Minneapolis Star Tribune, to Marie Claire, The Writer, and He also has authored, coauthored or edited 12 books. His writing awards are many: He has won the National Headliners Award for magazine writing five times. He has been named Writer of the Year by the City & Regional Magazine Association, and Journalist of the Year by the Milwaukee Press Club. As a staff writer with the Minneapolis Star Tribune, he was nominated for the Pulitzer Prize and chosen as a finalist for the Robert F. Kennedy Award. In previous lives, Chandler worked construction, drove a cab and played the banjo (not necessarily at the same time). He has toiled as a writer and journalist for three decades now and, unmindful of his sage father’s advice, has nothing to fall back on. Yet he is not without a specialized set of skills: He can take notes in the dark and is pretty good with active verbs.