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U.S. Senate candidate Jim Oberweis told the City Club of Chicago at Maggiano's restaurant Tuesday that  "I'm going to win in 2014" after the perennial candidate was asked if he would run against Sen. Mark Kirk in 2016.
Jose M. Osorio, Chicago Tribune
U.S. Senate candidate Jim Oberweis told the City Club of Chicago at Maggiano’s restaurant Tuesday that “I’m going to win in 2014” after the perennial candidate was asked if he would run against Sen. Mark Kirk in 2016.
Chicago Tribune
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When an audience member at a recent City Club of Chicago luncheon asked state Sen. Jim Oberweis if he planned to challenge U.S. Sen. Mark Kirk, a fellow Republican, in 2016, the question drew nervous laughter from the crowd.

Oberweis, who is attempting to unseat Democratic Sen. Dick Durbin in the Nov. 4 election, waved it away as a “toss-up ball.”

“I’m going to win in 2014, so I don’t even have to think about that,” he said.

That kind of optimism is typical of a candidate. But it doesn’t take a political expert to know that Oberweis faces long odds against Durbin, a veteran lawmaker whose support extends across the state.

Oberweis, like his opponent, is well-known to voters, but for different reasons: The heir to a boutique dairy company that carries his family name, Oberweis has been on the ballot almost continuously for more than a decade. He has lost two prior bids for Senate, two bids — in the same year — for U.S. House and one bid for governor. He sank more than $9 million of his personal wealth into those failed efforts, records show.

Oberweis won his state Senate seat in 2012 — the only campaign for public office that didn’t cost him a penny — but was back on the trail less than a year later, eyeing the Durbin seat even as some establishment Republicans dismissed it as another losing battle.

Oberweis sees things differently. According to him, he entered the race batting .500, having won three previous primaries, a seat on the state GOP’s central committee and the general election for state Senate.

“Not great, but certainly not embarrassing,” Oberweis told the Tribune’s Editorial Board in February.

Oberweis, 68, has lived in the same home in west suburban Sugar Grove for 37 years. He and his second wife, Julie, bought a condo in Bonita Springs, Fla., in 2010, but Oberweis said he doesn’t spend much time there because of duties in Springfield.

He said his business experience makes him well-suited for tackling problems in Washington.

Oberweis took over the family dairy business and grew it from one store and 50 employees to 43 stores and 1,200 employees, he has said. He also started a stock brokerage and an asset management firm, which oversees about $1.3 billion in assets. He says his sons now run both the dairy and the investment ventures.

The businesses have done well. A Senate disclosure form filed in January showed his net worth in the range of $12 million to almost $60 million. He and his wife reported an adjusted gross income of more than $1.37 million in 2013 and just over $1.06 million in 2012.

Oberweis also heads a charity foundation that carries the family name. He gave $16,700 to the charity in 2013, the most recent year for which records are available. Since 2007, the charity has given out more than $365,000, including nearly $80,000 to a food bank in Geneva and more than $60,000 to an Aurora homeless shelter, according to tax filings. The charity has also been generous to politically oriented organizations, giving $25,0000 in 2007 to the Koch brothers’ Americans for Prosperity and $16,000 in 2011 to the Springfield-based United to Restore Freedom records show. In 2012, the charity gave $6,000 to the Professional Golfers Association Foundation.

Oberweis’ personal wealth has also allowed him to put at least $1 million into this campaign, bringing his total investment in his political bids, including loans and contributions, to more than $10 million over the years.

But his relationship with his party has been rocky, which might explain why his top-of-the-ticket candidacy has gone largely ignored by fellow Republicans. Even Kirk has kept his distance from the race, although Oberweis said Kirk did attend a fundraiser for him in Chicago.

Oberweis angered anti-abortion activists in 2001 when he answered a question about abortion with a reference to the Taliban and “what can happen if we try to impose our religious beliefs on others.” Oberweis, who is Catholic, describes himself as “pro-life.” He thinks abortion opponents should focus on “common ground” issues like late-term abortions, parental notification and preventing taxpayer funding of abortions.

He frustrated moderate Republicans with a 2004 ad that featured him riding over Soldier Field in a helicopter while asserting that enough “illegal aliens” cross the border to fill the stadium every week. (He has since said that the ad was a mistake.) And he launched a 2006 bid for governor in apparent retaliation for being denied a leadership post with the Republican State Central Committee.

But Tim Schneider, chairman of the Illinois Republican Party, praised Oberweis as a “successful business owner who believes in strong fiscal policy,” and added: “Most people I talk to in Illinois are looking for a different direction, and Jim Oberweis offers a different direction.”

Last year, shortly after he entered the state Senate, Oberweis took up the cause of establishing higher speed limits on Illinois’ roadways, even as fellow Republicans warned him off because the idea had proved in the past to be a political loser. Oberweis succeeded in passing a bill that raised the limit on rural interstates, effective in January.

Oberweis pushed more legislation this year to raise speeds for big trucks on interstate highways in the Chicago area and to hike the limits on tollways, but those bills were vetoed by Gov. Pat Quinn.

Oberweis introduced another transportation-related measure late last year, seeking to repeal the long-standing ban on retail car sales on Sundays. But he was slow to figure out the politics involved.

“I thought I would be the champion of the automotive sales industry by getting government off their backs and allowing them to be open on Sunday,” Oberweis explained in an email to the Tribune. “As it turned out, consumers would like to buy cars on Sunday but the majority of the new car dealers prefer being closed on Sundays and they don’t want any competitor to be able to sell on Sunday.”

The ill-fated bill was left to bounce around Senate committees.

Even on a frivolous matter, he has met frustration. After the House defeated the Senate in a softball game, Oberweis, a chess enthusiast, passed a resolution in the Senate that challenged the House to a chess match. But he said “nothing came of that.”

Oberweis is one of just six Illinois state senators to receive a top rating from the American Conservative Union, meaning his votes on key bills aligned exactly with the group’s positions. He voted for the pension reform bill, against creating a gun registration system and against the same-sex marriage bill.

Still, Oberweis said he has learned how to work with Democrats during his short time in Springfield and would bring that skill to Washington. He points to his work with Sen. Martin Sandoval, a Chicago Democrat who has been his counterpart on the speed limit legislation.

“We’ve actually become friends and we’re known around Springfield as the ‘odd couple’ because we have been able to work together to solve legislative problems,” Oberweis told the Tribune Editorial Board last month.

Sandoval did not respond to requests to discuss his dealings with Oberweis.

kgeiger@tribune.com

Twitter @kimgeiger