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When a well-worn political springboard falls short.

As state Sen. Chris Larson faces incumbent Milwaukee County Executive Chris Abele in the April 5 election, Larson also faces a historical hurdle: No state senator has ever won the executive’s office. That might seem insignificant – until you realize that in the 56 years since the exec’s job was created, sitting or former state senators have won every election for Milwaukee mayor. They’ve also triumphed in every Milwaukee-based congressional campaign since 1982, all races for city treasurer since 1976 and the 2015 contest for Waukesha County executive.

That’s three Milwaukee mayors, two city treasurers, four U.S. reps (including Mayor Tom Barrett) and one Waukesha County exec with state Senate roots. So why have exactly zero of Milwaukee County’s six executives arisen from a similar background?

“In politics, size matters,” says University of Wisconsin-Milwaukee professor Mordecai Lee, himself a former state senator. State senate districts (composed of about 175,000 constituents) occupy large chunks of Waukesha County and the city of Milwaukee but lesser pieces of Milwaukee County (home to more than 950,000 people), providing a smaller base from which to run.

Also important: who you’re running against. Voters strongly favor re-electing incumbents, including now-Gov. Scott Walker, who beat state Sen. Lena Taylor in 2008. Abele’s personal fortune helped him eliminate former state Sen. Jim Sullivan in the 2011 primary and defeat then-state Rep. Jeff Stone in the general election.

And in county exec races, the edge often belongs to county board chairmen, insiders who once ran all Wisconsin counties. Milwaukee County’s first two executives, John Doyne and Bill O’Donnell, were former chairs, and in 1992, voters elevated another chairman, Tom Ament.

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Larson faces challenges besides history – three top aides have departed since November. But Larson says he’s beaten history before. As a young county supervisor challenging then-state Sen. Jeff Plale in 2010, he was told by many a progressive Democrat had never won the southern Milwaukee County seat. After a few weeks, he says, “They stopped saying that.”

‘The Jinx’ appears in the March 2016 issue of Milwaukee Magazine.

Find the March issue on newsstands beginning Feb. 29.

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