Whitaker's Iowa connections boosted his career but raise 'troubling questions' for Democrats

Acting Attorney General Matt Whitaker speaks at the annual Veterans Appreciation Day ceremony at the Department of Justice in Washington, D.C., on Nov. 15, 2018. (Photo: Nicholas Kamm/AFP/Getty Images)
Acting Attorney General Matt Whitaker speaks at the annual Veterans Appreciation Day ceremony at the Department of Justice in Washington, D.C., on Nov. 15, 2018. (Photo: Nicholas Kamm/AFP/Getty Images)

Matt Whitaker, the acting attorney general appointed by President Trump to replace Jeff Sessions, has deep roots in Iowa — and a history there that a leading Democrat says “raises troubling questions” about how he has used his official powers.

Born in Des Moines in 1969, the burly Whitaker first made a name for himself playing for one of the state’s two big football schools. He was a tight end on the University of Iowa Hawkeyes team that went to the Rose Bowl in 1991 and returned to the university for law school and a business degree.

After graduating in 1995, he began a career as a modest commercial attorney. Over the course of the next nine years, Whitaker held four jobs — a year at one law firm, two years at another, four years as in-house counsel to a chain of grocery stores, then another three years at yet another law firm.

During his time at that last law firm, Finley Alt Smith, it appears that Whitaker began a serious effort to break into politics. He called an old law school friend, Charles Larson Jr., who had become the head of the Iowa Republican Party, and pitched himself for the state treasurer’s race.

“I knew immediately he’d be a great candidate,” Larson told the New York Times. “He’d be exactly the type of candidate we’d love to have run. He had a great profile as an attorney and former Hawkeye. There’s always appeal there.” Larson’s assistant told Yahoo News he was traveling outside the country and would be unable to comment on this story.

Whitaker secured the Republican nomination for state treasurer in 2002. Campaigning alongside Sen. Chuck Grassley brought him into contact with the state’s Republican establishment. Whitaker lost, but the party did not forget him.

Within two years, according to the Des Moines Register, Whitaker’s name was on a shortlist of three candidates to be U.S. attorney for Iowa’s southern district submitted by Grassley to President George W. Bush. In February 2004, Bush picked Whitaker, whose title at Finley Alt Smith at the time was simply “attorney.” He was confirmed in the summer.

Whitaker’s rapid rise seemed to owe more to his connections than to experience. On the Senate questionnaire Whitaker filled out for his U.S. attorney appointment, he listed small-time disputes, including a breach of contract matter involving a dry cleaner and a personal injury claim of a pedestrian struck by a car, as the “most significant litigated matters” he handled up to that point. He had no criminal law experience and had not previously worked in government.

Though he doesn’t appear to have been doing high-level work, Whitaker was well thought of at his firm, according to Kevin Driscoll, a partner who supervised his work. “He was a good lawyer — good on his feet, good in court,” Driscoll said. “We were sorry to see him go but happy for him.”

Whitaker served five years as U.S. attorney. His term didn’t make many major headlines, but he courted controversy with one prosecution. In 2007, Whitaker’s office indicted Democratic State Sen. Matt McCoy on public corruption charges, alleging that he had demanded kickbacks from a private security company. The case went to trial but fell apart when a key informant’s credibility crumbled. A jury acquitted McCoy on all counts after two hours of deliberation. Whitaker’s prosecution of McCoy was dogged by allegations of political bias. A Des Moines Register columnist suggested the case had partisan roots and noted that it was brought at the same time as Bush administration political appointees had been accused of pressuring U.S. attorneys to advance Bush’s political agenda. That scandal eventually led to the resignation of Attorney General Alberto Gonzales.

Sen. Dianne Feinstein, D-Calif., referenced the McCoy case at a hearing of the Judiciary Committee on Thursday.

“Mr. Whitaker’s record also raises troubling questions about his potential misuse of official authority for political purposes,” Feinstein said. “Iowa state Sen. Matt McCoy has alleged that, while U.S. attorney, Whitaker targeted him for prosecution because he is an openly gay Democrat.”

In the wake of Whitaker’s appointment as acting attorney general, McCoy has reemerged as one of his more prominent critics. In a conversation with Yahoo News, McCoy said that, based on Whitaker’s history, he expects the acting attorney general could use the Justice Department to target Trump’s enemies.

“He truly has climbed the ladder by stepping on people’s necks and using pure political power,” McCoy said of Whitaker.

Whitaker spoke to state and local law enforcement on efforts to combat violent crime and the opioid crisis, on Nov. 14, 2018, in Des Moines, Iowa. (Photo: Steve Pope/Getty Images)
Whitaker spoke to state and local law enforcement on efforts to combat violent crime and the opioid crisis, on Nov. 14, 2018, in Des Moines, Iowa. (Photo: Steve Pope/Getty Images)

Whitaker’s stint as U.S. attorney ended in late 2009 when President Barack Obama replaced him. He returned to private practice, again handling small-time disputes. Eventually he built a practice specializing in criminal law — and lobbying the state legislature. He also participated in a series of business ventures, some of which have fueled the controversy over his appointment.

MEM Investment, a company founded by Whitaker and two partners, was awarded a loan by the city of Des Moines in 2012 to renovate an apartment complex for affordable housing. In 2016, the city terminated the loan agreement and accused Whitaker of having “abandoned the property.” Whitaker’s company also defaulted on a second loan and was accused of failing to pay contractors. He had become MEM’s sole owner in 2014. His company ultimately sold the building to another developer.

In 2014, Whitaker joined the board of World Patent Marketing. Last year, the Federal Trade Commission accused the company of defrauding customers. The FTC complaint says the company swindled inventors by promising to market their inventions to manufacturers — for large fees — and then failing to deliver. Whitaker rebuffed the FTC’s efforts to subpoena him for records related to the company, and an FBI investigation is ongoing. According to the Washington Post, the Justice Department declined to comment on Whitaker’s handling of the subpoena. A DOJ spokesperson told the paper Whitaker was “not aware of any fraudulent activity” at the company.

The Iowa Democratic Party called these business ventures “ethical failures” by Whitaker in its statement on Thursday that raised concerns about his appointment. McCoy, the Democratic state senator, described Whitaker’s business record as the “wreckage from his past.”

Whitaker returned to politics in 2014 when he ran for U.S. senator. Sam Clovis, a longtime friend in Iowa politics who went on to become a Trump campaign official — and has figured in the special counsel’s investigation of the 2016 campaign — was running for the same seat. After they both lost the primary, Whitaker began working with his former rival. Clovis followed his Senate run by mounting a new bid for state treasurer, with Whitaker serving as chairman of his campaign. That campaign was unsuccessful as well and, one month before the election, Whitaker became the executive director of the Foundation for Accountability and Civic Trust. The nonprofit organization, which was funded by undisclosed conservative donors, attacked Democrats for alleged legal and ethical issues. The board of FACT included Whitaker, his law partner William Gustoff, and Neil Corkery, who also sits on the board of the Judicial Crisis Network.

In 2016, with Whitaker as its sole full-time employee, FACT repeatedly went after Trump’s opponent, Hillary Clinton. Whitaker argued that a special counsel was “urgently needed” to investigate Clinton’s use of a private email server.

Whitaker’s past comments and close ties to Clovis have many Democrats concerned he may try to thwart special counsel Robert Mueller’s probe. Sen. Mark Warner, a Democrat from Virginia, has cited the friendship between the two as a “blatant conflict of interest” that would require Whitaker to recuse himself from supervising the investigation.

Whitaker and the Department of Justice did not respond to requests for comment from Yahoo News about the calls for his recusal and other concerns surrounding his appointment.

Though Democrats worry that Whitaker could interfere with Mueller’s work, some on the Hill concede their options are limited. With Republicans leading the Senate Judiciary Committee, one Democratic congressional aide who spoke to Yahoo News admitted the opposition has few options other than perhaps making Whitaker testify before the House Judiciary Committee, which will be controlled by Democrats after the new Congress is seated in January.

In the Senate, Democrats are also working with some Republicans to push a bill that would protect Mueller from being fired. Thus far, that effort has been blocked by Republican Senate Majority Leader Mitch McConnell. Some Democrats have speculated about an effort to attach a bill to protect Mueller to a must-pass appropriations bill before the end of the current Congress. This week, Democrats sent a letter to the DOJ’s top ethics official advancing the argument that Whitaker’s ethical issues require his recusal from overseeing the Mueller investigation.

Other than those efforts, Democrats likely can’t do much about Whitaker other than loudly ringing alarms. And Whitaker’s Republican allies are clearly pleased with his selection.

After Whitaker’s appointment was announced on Nov. 7, Grassley issued a statement noting that he’s known the acting attorney general for “many years.”

“Matt will work hard and make us proud. The Justice Department is in good hands during this time of transition,” Grassley said.

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