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In April 2003, the Republican U.S. senator Peter Fitzgerald announced he would not seek a second term, and Oberweis entered the crowded race to succeed him. “Peter Fitzgerald surprised the world. . . . And over the next 48 hours I got . . . over 100 phone calls from people saying would you please run for this seat,” Oberweis says of his decision to run again.
In the same way the abortion flap derailed his first campaign, Oberweis’s 2004 race was defined by a single event—the airing of a 30-second campaign commercial showing him aloft in a helicopter over Soldier Field, trying to illustrate the economic effects of illegal immigration. “Illegal aliens are coming here to take American workers’ jobs, drive down wages, and take advantage of government benefits such as free health care, and you pay,” Oberweis said gravely over the whir of the rotor. “How many? Ten thousand illegal aliens a day. Enough to fill Soldier Field every single week.”
The ad was panned as scaremongering, and Oberweis wound up finishing second, 12 points behind the nominee, Jack Ryan. Later that summer, when Ryan withdrew from the race following the release of his divorce files, state party officials resisted turning to Oberweis, instead importing the Maryland ideologue Alan Keyes to strike out against the Democrat, Barack Obama.
Oberweis says he regrets the abrasive tone of the helicopter ad, but sees its content as an example of his foresight. “This was an issue that I was way ahead of the curve on,” he says. “I was the only one willing to talk about it. I think that the country has come around to my viewpoint on this issue, but I think [the ad] did a lousy job of communicating that position.”
In 2006, Oberweis ran for governor—again, he says, after getting “hundreds” of calls from supporters. The Republican primary was a bitter, five-way election won by state treasurer Judy Baar Topinka, a moderate on social issues. Oberweis finished a relatively close second, but the race may have cemented his reputation as the Energizer Bunny of candidates. “Once you lose three races or so, you really have to fight a stigma of perennial candidate,” says the Cook Report’s Wasserman. “It’ll be very hard for Oberweis to shake the persona he has earned for himself as a kind of unsavory politician.”
“I think he loses elections because he’s perceived as a gentleman who wants an office so badly that he’ll do whatever or say whatever it takes to get there,” Topinka says now. “There are certain rules to the game—certain civil ways of handling elections—and I think one of Jim’s problems is that he never put that line in the sand beyond which he would not go.”
The line between a well-traveled, serious contender and an office-shopping perennial can be blurry. Once an aspiring candidate has crossed, it’s virtually impossible to return. In 1948 Harold Stassen was a promising young governor of Minnesota when he finished second for the Republican presidential nomination. He ran again in 1952, winning some delegates, before running again and again for a total of nine bids between 1964 and 1992, never coming close to the success of his first run. Stassen also ran unsuccessfully for the U.S. Senate (twice), for governor of Pennsylvania (also twice), and once for mayor of Philadelphia. Though a member of Dwight Eisenhower’s cabinet and a former president of the University of Pennsylvania, he is perhaps best known as a punch line on The Simpsons. (“Hey, who wants some eggs à la Harold Stassen?” Gil, the washed-up salesman, asks the Simpson family. “They’re always running!")
“We’re certainly not at the Harold Stassen stage yet,” says Kent Redfield, a political science professor at the University of Illinois at Springfield. But “you do get to a tipping point where you really can’t recover, and he probably is close to that. This may be pretty much it for his future as a serious candidate.”
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Oberweis refuses to say whether he would run again if he loses in November. The money he has spent trying to win office doesn’t seem to bother him. (“I think it shows a commitment to those who’ve supported me,” he says. “It also keeps me in a position where I can’t be overly influenced.") He dismisses the perennial candidate label as a media invention and says his close-but-no-cigar showings prove that voters want him. “In reality, I’ve run in five primaries and one special [election],” Oberweis says, referencing his victories in two GOP primaries held the same day: the special election to fill Hastert’s term and the regular party primary to decide who would be the GOP nominee in November’s general election. “Won two of the five primaries by a much bigger margin than I ever lost one by, and [in] all the other primaries there were three to eight candidates and I beat some pretty strong candidates. So voters have given us some pretty strong support.”
It’s unclear whether Oberweis gets discouraged. Patrick Joyce, the executive vice president of Oberweis’s investment firm since 1994, who referred to his former boss as a “visionary,” says, “Maybe a lesser person would’ve stopped . . . but I think his inner desire is so strong that he continues to move forward.” Each of Oberweis’s five children spoke of their father’s unshakable faith in himself, and Oberweis often referenced his entrepreneur’s resilience in bouncing back from blows personal and professional. “Every human being has their breaking point, and I don’t know where that would be for my dad,” Trish Oberweis tells me. “He’s human, so I’m sure it’s out there, but I don’t see it at this point.”
Oberweis resists saying where his breaking point is. The mounting losses and the public sneers do hurt him, Trish Oberweis says, but he seems to view them less as signs than as additional obstacles on his path to inevitable political office. “There was a guy about 130 or 150 years ago who had several losses before he won,” he says. “I can’t quite remember his name, but he went on to become the president of the United States. His first name was Abraham. What was his last name again?”