Now here’s a real blast-from-the-past. On Friday, the Chicago Tribune published an article where dairy magnet-turned-perennial-candidate-turned-Illinois state Sen. Jim Oberweis expressed interest in seeking the GOP nod against freshman Democratic Rep. Lauren Underwood, and he said he would make a decision in 30 to 60 days. Last year, Underwood flipped Illinois 14th Congressional District, a 49-45 Trump seat in the western Chicago area, and she’ll likely be a top GOP target. However, if history is any guide, Team Red can almost certainly do better than Oberweis.
That’s because Oberweis, who is one of Daily Kos Elections’ favorite frequent candidates going back to our Swing State Project days, 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.
Oberweis then managed to lose the 2004 Senate GOP nod twice. He first lost the primary to Jack Ryan, and after Ryan dropped out of the general election against Democratic state Sen. Barack Obama, party leaders passed over Oberweis in favor of fellow perennial candidate Alan Keyes. That was probably the wrong decision; while the seat was almost certainly unwinnable for Team Red by then, Keyes was an absolute disaster and lost to Obama 70-27; even Oberweis probably could have done a whole lot better than that.
Oberweis kept up his primary losing streak in 2006 by losing the gubernatorial contest by a pretty modest 38-32 against state Treasurer Judy Baar Topinka. But in 2008, Oberweis finally got to be Team Red’s standard bearer in a nationally watched 2008 special election to succeed former GOP Speaker Dennis Hastert.
That district, which was also numbered the 14th, 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 and is now awaiting charges of corruption, 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, and the next year, he launched a second longshot bid against Durbin. That campaign started on a strange note when Oberweis partly apologized for his crummy electoral record, saying, "I made statements and commercials that I regretted and I've said so." Oberweis also had to answer questions about why his wife was registered to vote in Florida, admitting that the couple has spent a lot of time in the Sunshine State and awkwardly defending himself by claiming that he's "been in the state Senate every day the Senate has been in session."
Oberweis finally won a statewide primary, but his 56-44 victory against an underfunded foe wasn’t exactly the stuff of legends. It hardly mattered, though, since the contest against Durbin was never on anyone’s radar, and Oberweis lost 54-43. In 2016, Oberweis was re-elected 55-45 even as his state Senate seat was swinging from 53-45 Romney to 48-45 Clinton.
Unlike in 2014, Oberweis would need to give up his place in the legislature if he ran for Congress. However, Illinois 14th District is more conservative than the seat he holds now, and despite his track record, he may have better odds against Underwood than if he seeks re-election.
Still, there’s no guarantee Oberweis would win the GOP nod. Navy veteran Matt Quigley has already announced he’s in, and the local political newsite Capitol Fax speculates that state Rep. Allen Skillicorn could run. We haven’t heard anything from Skillicorn about any interest, though Capitol Fax wonders if a potential congressional campaign would explain “why he’s been holding so many press conferences lately.”
