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Around 9 p.m. on March 8th of this year, shortly after calling his Democratic opponent to concede the race to fill the term of the retiring Republican congressman and House Speaker J. Dennis Hastert, Republican candidate Jim Oberweis made his way to the podium at the Q Center in far west suburban St. Charles to perform what for him has become almost a ritual. “Coming in first is a lot more fun than coming in second,” Oberweis told the crowd of dispirited supporters. “Unfortunately, we’re on the other side of that this time. I’m sorry we came up short, but we have another run at it in seven months.”
The special election was the fourth failed bid by Oberweis for major elected office. His loss put the 14th Congressional District of Illinois—a wide swath meandering west from the booming exurbs nearly to Iowa—under Democratic control for the first time in 70 years. Hastert had held the seat for more than 20 years and almost always won with more than 60 percent of the vote. Yet Oberweis, a 62-year-old multimillionaire dairy magnate and investment manager who has lived his entire life in the area and had Hastert’s backing, couldn’t beat the Democrat, Bill Foster, a mild-mannered physicist running in his first campaign. Oberweis has another shot in November—March’s special election decided only who would serve the final nine months of Hastert’s term—but he has now lost so many times that the prospect of a rematch gives many Republican stalwarts apoplexy.
“Oberweis’s ego has embarrassed the party enough,” harrumphed the conservative Chicago Tribune columnist Dennis Byrne in a column after Foster’s win.
“The cumulative results show that Oberweis plain-and-simple is not liked,” wrote the conservative blogger Tom Roeser shortly after the March defeat. “What has to happen before he understands this—someone to drive a political stake through his heart?”
In April, the House Republican leader, John Boehner, reportedly tried to do just that, saying he wanted Oberweis out of the race, according to Rich Miller, citing an anonymous source on his Illinois political blog Capitol Fax. The National Republican Congressional Committee, which spent more than $1 million on the first Oberweis campaign against Foster, nearly a quarter of its funds at the time, has withdrawn financial support for the rematch. And polling shows the outcome could be even more lopsided than the 53-to-47-percent loss in March. “It’s too early to say that this race is in the bag for Foster, but it is very rare that a candidate wins a special and then loses next time around,” says David Wasserman, the House editor of the nonpartisan elections newsletter The Cook Political Report.
With his sharp analytical mind, deep Aurora roots, and bulging bank account, Jim Oberweis would seem a lock for public office. But despite spending around $7 million of his own money in runs for governor, the Senate (twice), and Congress, he has yet to win a seat. His first marriage collapsed (at least in part because of his political efforts), and a strong reputation built on decades of running several successful businesses has been eclipsed by his political belly flops. He is perhaps best known now as the Milk Dud, a derisive play on the family dairy coined by the late Chicago Sun-Times political writer Steve Neal.
Yet Oberweis is undeterred. He says he is optimistic about the November race, but he won’t rule out future runs should he lose. In his 30 years as a stockbroker, Jim Oberweis got rich by picking winners. So why does he continue to invest in himself?
“He just has this confidence that—I don’t know where it comes from or how he maintains it—goes beyond confidence, just outright knowledge that he can make a difference,” says his daughter Trish Oberweis, an associate professor of criminal justice at Southern Illinois University at Edwardsville.
“I don’t believe I would be a normal, average individual legislator,” says Oberweis, who is tall and lumbering, with a slight paunch and a tendency to rap his hand against the table when making a point. “I have a history of making some things happen where people said it was impossible.”
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