Oberweis trying again for Congress; Will pour own money into Underwood challenge

WASHINGTON — State Sen. Jim Oberweis, R-Sugar Grove, who has poured millions of his own dollars into multiple failed bids for higher office, told the Chicago Sun-Times on Tuesday he is prepared to dip into his considerable wealth to beat freshman Rep. Lauren Underwood, D-Ill.

“I’m going to bring that seat back to the Republican side,” Oberweis said.

Oberweis will kick off his latest bid for Congress by making the rounds of Lincoln Day dinners in Dundee, DuPage and maybe McHenry County in the coming days.

Underwood pulled off an upset last November in defeating now former Rep. Randy Hultgren, R-Ill., outraising and outworking him to claim the 14^th District seat in what turned out to be a big Democratic year.

Underwood “is not distracted by politics. She is prioritizing being with her community after the senseless shootings last week,” said her political adviser, Ronnie Cho. Four of the five victims in the Aurora factory massacre lived in the 14^th District. Cho said Underwood called the family of each victim and attended a vigil in Aurora over the weekend.

On Tuesday, Underwood reported for jury duty in the Will County courthouse, not yet put on a case.

In a stark contrast to Hultgren, Underwood has been holding town halls. Last Saturday she was in Batavia with another freshman, Rep. Sean Casten, D-Ill.; Monday’s stop was in Crystal Lake; and Tuesday in Sycamore.

Oberweis, 72, is a wealthy investor and ice cream magnate whose stores in the Chicago area, now run by his son, bear the family name. He loaned or gave his campaign $1.6 million for a 2014 Senate bid and loaned or gave $3.8 million for two House contests in 2008.

Oberweis said that Underwood’s 2018 victory was due in part to the the millions of dollars Gov. J.B. Pritzker spent from his pocket on turning out the Democratic vote. In 2020, if need be, Oberweis said, “I will pay” to get out the GOP vote.

I asked him, “Do you think you would put about a million in the House race?”

He replied, “That’s possible.”

Underwood, 32, a resident of Naperville, where she was raised, is one of the standouts in the new class of Democrats, the rare African-American who won a House seat in a majority white district. Her congressional salary of $174,000-a-year is the most money she’s ever made, according to her financial disclosure report.

Oberweis’ runs for the House of Representatives, the U.S. Senate and governor have all ended in defeat:

* A 2014 Senate bid against Sen. Dick Durbin, D-Ill.

* In 2008, two House elections — a special and a general — to Rep. Bill Foster, D-Ill.

*A 2006 GOP primary for governor.

*A 2004 GOP primary for senator.

*A 2002 GOP primary for senator.

Oberweis triggered a controversy in his 2004 Senate run where he rallied against “illegal aliens.” Years later, immigration became President Donald Trump’s central issue.

“It is still a serious problem today because we haven’t dealt with that, we haven’t solved the problem,” Oberweis said. “I was just, I guess, too early in calling people’s attention to that. People weren’t ready to hear the message. And on top of that I did a lousy job with the message.”

I checked with Oberweis to see if a 2013 story I did was still true. Yes, Oberweis told me, his wife still is a legal resident in Florida. In 2013, as Oberweis was launching another U.S. Senate bid, Obeweis confirmed that his wife, Julie, became a Florida resident because of the “tax advantages” of the Sunshine State.

Democrats — national and in Illinois — are making the Underwood and Casten seats priorities to retain. With Trump on the ballot, there will be an enormous Democratic 2020 turnout in blue state Illinois.