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McCaskill faces a familiar political problem: her own wealth

McCaskill faces a familiar political problem: her own wealth


Recent published reports revealed that Sen. Claire McCaskill’s husband has profited handsomely from the very type of investments that the senator herself has legislated against.

It’s the kind of story that would create a speed bump for any political campaign. For McCaskill, a Democrat, it’s also the latest reminder of an ironic political liability — her substantial personal wealth — as she tries to convince regular Missourians that she’s “one of them” going into a tough re-election bid this year.

Roll Call lists McCaskill as the 24th wealthiest member of Congress overall, with an estimated net worth of almost $27 million — and the No. 1 wealthiest member who faces a tough campaign fight this fall.

Though personal wealth is about as common in the Senate as flag lapel pins, McCaskill has had particular problems with the issue over the years. The controversies sometimes (though not always) involve her husband, housing developer Joseph Shepard, whom she married in 2002 — the source of most of her wealth.

According to the report last week by the Kansas City Star, Shepard has made at least $230,000, and possibly far more, by investing in a hedge fund with ties to the Cayman Islands. The Caribbean nation is a notorious tax haven for wealthy American investors — notorious enough that McCaskill co-sponsored unsuccessful legislation almost a decade ago targeting the practice as “economic warfare against the United States, and honest, hardworking Americans.”

That story followed a Post-Dispatch report revealing that Shepard had invested at least $2.25 million in tax breaks for conservation easements, a class of investments that the Internal Revenue Service has called into question and Congress is trying to restrict. McCaskill has supported those efforts.

McCaskill and Shepard file their taxes separately. Shepard declined to comment, according to the report. McCaskill’s office put out a statement saying she “does not make decisions on public policy based on what’s best for her husband,” and offering as proof her sponsorship of the tax haven legislation and her more recent opposition to Republican tax cuts that will aid the wealthy more than others.

Hitting a senator for the business practices of her spouse — particularly a practice the senator had attempted to outlaw — may seem a weak blow.

But a key measure of every political controversy is: Does it fit an existing narrative? In McCaskill’s case, the narrative, for years, has been one of a down-home public persona repeatedly undermined by her personal wealth.

“Missouri is seen as a very average state with common folk who will vote in November in part on whether or not they can identify with the individuals running for office,” said Dave Robertson, political scientist at the University of Missouri-St. Louis. The latest story, he said, “plays on some of the themes that she’s been vulnerable to in the past.”

Among them:

• In 2011, it came out that McCaskill had charged taxpayers for flights in a private plane she owned with her husband and that she had failed to pay almost $300,000 in personal property taxes on it. She ultimately paid back the public funds, caught up on the taxes and got her husband to “sell the damn plane,” but not before being tagged with the nickname “Air Claire” by her critics.

• While conducting one of her many “town hall”-style meetings last year, McCaskill unintentionally revived conservative cries of “Air Claire” when she appeared to agree with a questioner’s assertion that “normal people” could afford to fly private planes.

• This month, conservative social media erupted over a report implying that during a recent four-day RV campaign tour of Missouri, McCaskill actually was flying overhead in her current private plane. McCaskill strongly denied the crux of the report, but in the process confirmed that she did in fact fly to her overnight accommodations during to trip and flew to one campaign stop that had been added late.

McCaskill’s defenders point to her modest personal biography: a Rolla native who waitressed her way through college and was for a time a single working mother.

Still, the National Republican Senate Committee, which has made McCaskill a top target this year, gleefully tweaks the topic of her current wealth every time it comes up. Reacting to the Roll Call wealth ranking this year, the NRSC issued an online statement refocusing attention on McCaskill’s $2.7 million Washington condo, and the high-end restaurant she is invested in there, “where a bottle of wine can run you $350.”

“That bottle of wine is pretty cheap compared to the local shopping like Hermes, Louis Vuitton and Gucci,” the statement noted, “where just one bag could run you up to $10,000!”

There’s some irony to GOP criticism of McCaskill’s wealth, of course, given that Republican President Donald Trump is by far the richest person ever to occupy the White House.

“It’s inexplicable that they think they can disqualify me because my husband is a successful businessman in the era of Donald Trump,” McCaskill told Politico in an interview last August. “If my husband were married to a Republican U.S. senator, they’d hold a ticker-tape parade for him.”

Unlike McCaskill, Trump has made no effort to play down his wealth, bragging about it regularly from the earliest days of his 2016 campaign up through a rally held this week. His supporters have generally cheered those pronouncements.

“They are big damn hypocrites,” Missouri Democratic Party Chair Stephen Webber said in a statement this week. “Donald Trump’s vast wealth and business success is wonderful, but somehow Claire’s husband’s business success and wealth is bad. Give me a break.”

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