Issa defeated DeMaio after a very expensive and very ugly battle. Issa launched a TV spot in January that, in addition to relying on the racism against Hispanics that has become a staple of GOP ads during the Trump era, also repeatedly reminded the viewer that DeMaio is gay. The commercial drew condemnation from several local Republicans, but Issa stood by the ad and unconvincingly argued that he didn’t consider the word “gay” to be a slur.

Issa continued to run more racist ads against DeMaio over the next few weeks that argued that the former councilman was on the wrong side of Trump when it comes to immigration. DeMaio himself also aired commercials claiming that Issa was the one who had been disloyal to Trump, but it wasn’t enough.

If Issa wins this fall, he’ll revive a political career that seemed all but dead just months ago. Progressives across the nation were delighted in January of 2018 when Issa, who spent years using his position as chair of the House Oversight Committee—and millions in taxpayer dollars—to launch bogus investigation after bogus investigation against the Obama administration, announced that he would retire from Congress.

Issa's decision came just over a year after he'd narrowly won re-election in the 49th District, a once-safely red seat that had swung from 52-46 Romney to 51-43 Clinton; that fall, Democrat Mike Levin went on to decisively flip Issa's constituency.

However, while Issa was done with the 49th District, he wasn't actually done with Congress. Weeks after he announced he would retire, reports emerged that Issa was considering switching to the 50th District if Hunter, who was under investigation for misusing campaign money, resigned. Hunter refused to go anywhere, though, and Issa wasn’t on the ballot anywhere in 2018.

Trump picked Issa to lead the U.S. Trade and Development Agency in September of that year, but his nomination quickly stalled in the Senate. After months of waiting, Issa decided to form an exploratory committee in the summer to run against Hunter, who was now under indictment but insisted he’d run for re-election. Before Issa announced if he’d seek the 50th District, though, the Senate Foreign Relations Committee scheduled a confirmation hearing that would have taken place exactly a year after Trump first picked him.

Issa said he wouldn’t try and return to Congress if he got the Agency post, but he never got confirmed. Instead, New Jersey Sen. Robert Menendez, who is the committee's top Democrat, called for the hearings to be delayed, saying that information in Issa's FBI background check was "problematic" and "potentially disqualifying." Menendez didn't reveal what those bogeys were, but Republican Sen. Jim Risch, the committee's leader, agreed to postpone the hearings until the Trump administration gave Issa's file to the full panel.

We never got to find out what was in the document, since Issa quickly withdrew his name from consideration and launched his congressional comeback bid. Issa himself argued that Menendez was simply rehashing public information about the former congressman's time in the Army nearly 50 years ago: That military career included a demotion and an "unsatisfactory" conduct rating, as well as an allegation that Issa stole another soldier's car. However, Menendez said there was more troubling information in Issa's file, adding, "If they were all public, then we wouldn't be having the difficulty that we have."

Issa’s bid to succeed Hunter, who pleaded guilty in December and resigned a month later, went considerably better, though. While The Hill had reported in June that many House Republicans didn’t want Issa back because he’d “rubbed colleagues the wrong way,” House Minority Leader Kevin McCarthy ended up endorsing his comeback campaign. Both Issa and DeMaio raised more money during the final three months of 2019 than any non-incumbent Republican candidate in any of the nation's other House races, but the uber wealthy Issa also threw down plenty of his own cash.

While Issa’s victory last week gives him a strong chance to revive his long political career, the outcome is yet another narrow defeat for a man who has long been talked about as a rising California Republican star. DeMaio, who was arguably the most prominent gay Republican officeholder in the nation, was Team Red’s candidate in 2012 to lead San Diego, but he lost to then-Democratic Rep. Bob Filner 52-48.

National Republicans were thrilled the following year when DeMaio launched a bid to take on Democratic Rep. Scott Peters in the 52nd District: DeMaio even decided to stay in that race after an early 2014 special election was scheduled to succeed Filner, who resigned after multiple women accused him of harassment. The mayoral contest was won by fellow Republican Kevin Faulconer, but DeMaio lost his own expensive battle against Peters 52-48 later that year.

DeMaio soon became a prominent conservative radio host in the San Diego area, and he was the face of the 2018 effort to both repeal a gas tax the legislature passed the previous to fund highway improvements and to recall state Sen. Josh Newman for voting for the bill. Newman did lose the recall campaign that June, but the gas tax repeal went down in flames in November 57-43. DeMaio left his gig last summer to run for Hunter’s 50th District, but this campaign ended in yet another close loss for him.

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