In fact, the wealthy dairy magnate has unsuccessfully run for the House or statewide office a grand total of six times beginning with his 2002 primary defeat to take on Democratic Sen. Dick Durbin. We’re even going to be nice and not count Oberweis’ accidental 2020 Senate campaign against him.

Oberweis' most high-profile loss came in 2008, which came after three failed statewide primary campaigns. That year, Oberweis was the GOP nominee in a high-profile special election to succeed former House Speaker Dennis Hastert. That district, which was also numbered the 14th (but only shared about 40% of the same territory as the seat he’s now running for), had been reliably red turf for a long time. George W. Bush carried the seat 55-44 in 2004 and Hastert (whose awful past would not be revealed until 2015), had always won re-election easily.

However, the contest between Oberweis and Democrat Bill Foster was a competitive affair, and Foster’s 52.5-47.5 victory was a strong and early sign that 2008 was going to be a very good year for Democrats. Oberweis and Foster had won their primaries for the regular November contest months before the special was decided, and Republicans reportedly tried to convince their nominee to drop out.

Then-state Rep. Aaron Schock, who was the GOP nominee for a congressional seat to the south, loudly threw Oberweis under the bus for his defeat, declaring, “Anybody in Illinois who knows Jim Oberweis knows that was not a referendum on the Republican Party; it was a referendum on Jim Oberweis.” Schock, whose own congressional career would self-destruct the next decade, also volunteered that when it came to Oberweis, “The people that knew him best, liked him least.” Oberweis didn’t listen, and he lost to Foster again 58-42.

Things finally changed in 2012 when Oberweis won both the primary and the general election for an open state Senate seat. But some habits can't be broken: The next year, he launched a second longshot bid against Durbin, which characteristically ended in defeat. Still, Oberweis was re-elected the following cycle 55-45 even as his state Senate seat was swinging from 53-45 Romney to 48-45 Clinton, so it’s possible that he’s developed some better campaigning skills in the last few years.

Oberweis announced in 2019 that he would challenge Underwood, but strangely, he didn’t rule out running for Congress in Florida later that year. Oberweis owns a home in retiring GOP Rep. Francis Rooney’s seat in the Naples area, and he’s benefited in the past from a homeowner's tax exemption by listing it as his "primary" residence. In October, an Oberweis spokesman acknowledged to Politico, "There's a push from Republicans in that district" for him to run, and he continued, "All he'd have to do is move down there and he'd win."

Oberweis did not move down there and win, though. Instead, he now has another chance to avenge his last six defeats in Illinois in November by taking on Underwood in what will likely be a very competitive race for a seat the GOP very badly wants to take back.

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