Under Pressure: SCOTUS Fight Could Strangle Claire McCaskill's Re-election Hopes

Posted: Jul 08, 2018 3:00 PM
Under Pressure: SCOTUS Fight Could Strangle Claire McCaskill's Re-election Hopes

Sen. Claire McCaskill is about 24 hours away from feeling the immense pressure of this Supreme Court battle on her political career. She’s going to feel like Atlas. Unlike 2012, there haven’t been a lot of local GOP foul-ups. There have been no idiotic remarks about rape this go around—and Gov. Eric Greitens, who could have posed a problem for Republicans down ticket for his sordid affairs, including a sexual assault allegation, has resigned. McCaskill faces re-election in a state that broke for Trump by a near 20-point margin. She’s going to need every vote she can get come Election Day and right now, she’s struggling with a key group: black voters. They’re been wondering where the hell she’s been. They’re not sliding into the GOP camp, though they don’t see a reason to get excited about McCaskill. That unenthused feeling could be exacerbated among Democrats in general if she decides to vote for President Trump’s Supreme Court nominee (via AP):

U.S. Supreme Court Justice Anthony Kennedy’s retirement has presented Missouri Democratic Sen. Claire McCaskill with a choice that could make or break her chances of being re-elected to a third term.

If McCaskill, a self-described moderate, votes against President Donald Trump’s pick, she could alienate voters who handed him a 19-point victory in Missouri two years ago. But voting for Trump’s nominee could spur backlash from Democrats, and she’s already faced pushback from some black Democrats who feel ignored by her.  


“It’s a difficult situation for her simply because she’s going to get a lot of pressure from the Democratic base to resist any nomination, and at the same time she can’t really portray herself as an obstructionist because she is trying to move to the political middle,” University of Missouri-Columbia political scientist Peverill Squire said.


So far, she’s taken a wait-and-see attitude on a nominee for Kennedy’s seat, and in a statement said it’s “premature to discuss his replacement until one has been nominated.” Squire said McCaskill will likely hold off on making a decision to see what kind of response Trump’s pick will get.

The Missouri GOP is hoping to use this fight to grill McCaskill, who voted against now-Justice Neil Gorsuch when his nomination was being debated in the Senate. Yet, AP added that it could energize Democrats, given their staunch support for abortion rights, and could produce a boom in fundraising. McCaskill should see some of that cash from the national party, though those checkbooks could be closed and support from the grassroots closed off if she votes in favor of whomever the president selects tomorrow. Thus far, McCaskill has voted against key Trump picks for SCOTUS and the CIA, the latter being a zero hour decision to minimize exposure. And she’s been silent on how the Trump tax cuts have benefitted her state.  

This is just one front. McCaskill has been tripped up with her RV tour drama, where she admitted to using her private plane for part of the trip. The tour occurred last month, though The Washington Free Beacon found that the RV took a very similar as that of McCaskill's private plane (via Politico):

Sen. Claire McCaskill confirmed Tuesday that she used her private plane during a three-day RV tour of her state last month, an admission that promises to become a political headache for the Missouri Democrat in her reelection bid.

McCaskill claimed that a report on her air travel in The Washington Free Beacon, which used aircraft tracking data to map the plane's path following her RV tour for two of its three days, was "not accurate." However, she went further than the publication did in confirming that she did use a plane for part of the tour.

"I added some stops with the use of the plane, but I was on the RV so much that the broken drawer drove me crazy," McCaskill said in a brief Tuesday interview in the Capitol, adding that "I even lost an iPad around a corner on the RV."

She disputed the notion that the use of the plane allowed her to "pretend" that she was using an RV rather than the multi-million-dollar plane, reportedly purchased by her husband's company in 2013. 

It’s a mess because it goes deeper than this. In 2011, she sold her first private plane after neglecting to pay $300,000 in taxes on it. In 2017, she had an out of touch moment when she claimed that normal citizens could afford private travel. On top of this, she might get hit over her husband’s Cayman Islands cash. Now, she and her husband, Joseph Shepard, file their taxes separately. Shepard invested in a hedge fund tied to the famous tax haven and accumulated $230,000-2.1 million in income. McCaskill is against tax havens and has voted for legislation that targeted them (via The Kansas City Star):

As a U.S. senator, Claire McCaskill supports cracking down on offshore tax havens.

But the Missouri Democrat's husband has invested $1 million in a hedge fund tied to the Cayman Islands, one of the world's most notorious tax havens.

Joseph Shepard's investment in Matrix Capital Management has earned him between $230,000 and $2.1 million in income since he first invested in 2013, according to McCaskill's financial disclosure forms. Such forms only show a range of income.

If Shepard declares his investment on his taxes, he doesn't directly enjoy much of a tax haven. The earnings would be subject to capital gains tax back in the U.S.

The capital gains rate, however, is lower than the income tax most working Americans have to pay.

Shepard declined to comment for this article. He and McCaskill file their taxes separately, and while she has released her tax information publicly in the past, Shepard never has.


McCaskill was a co-sponsor of the 2009 Stop Tax Haven Abuse Act. The unsuccessful bill targeted the Cayman Islands among several countries identified as tax havens "engaged in economic warfare against the United States, and honest, hardworking Americans."

For now, Republicans and Missouri Attorney General Josh Hawley, the presumptive GOP Senate nominee, are more focused on using the upcoming SCOTUS fight to apply pressure on McCaskill (via Politico):

Democratic Sen. Claire McCaskill is likely to oppose President Donald Trump’s Supreme Court nominee for being too conservative. And her Republican opponent for reelection, a constitutional lawyer who once clerked for Chief Justice John Roberts, is itching to make her pay.

“She’s been wrong on every single court nominee since she has been running for the Senate or in the Senate. So I’m not surprised in the least,” Josh Hawley, Missouri’s attorney general, said in an interview, sitting in a pickup truck with the AC blasting after marching in a July 4 parade.

"It is,” he added, “the defining issue of this campaign."

If the pre-nomination clash between McCaskill and Hawley is any sign, the Supreme Court confirmation battle over Trump’s high court nominee will reverberate in Missouri more than any other Senate battleground this year. Unlike a trio of other red-state Democrats on the ballot — Heidi Heitkamp of North Dakota, Joe Manchin of West Virginia and Joe Donnelly of Indiana — McCaskill opposed Neil Gorsuch last year.

Republicans and Democrats expect that she’ll do the same again this time: Notably, the liberal group Demand Justice is laying off McCaskill in a $5 million ad blitz designed to persuade centrist Democrats not to break ranks. And Trump did not extend her an invite to the White House last week as he talked about the court with a group of centrists.

The Missouri Democrat is not optimistic that the president will pick someone she could vote for in the Senate. Politico added that the 2016 Supreme Court battle helped put Sen. Roy Blunt over the top against Democrat Jason Kander. With the final confirmation vote occurring in the fall, we’ll see if conservatives pull through again in the Show Me State.