In 2004, when he started a five-year stint as U.S. attorney in the Southern District of Iowa, Whitaker cited a personal-injury case and a dispute involving a dry-cleaning business as some of his most consequential legal work. When he left office, he started a modest legal practice and a short-lived lobbying and consulting firm.
Whitaker, 49, stands in vivid contrast to his predecessors, whose résumés typically boast judgeships, partnerships at prestigious firms and senior roles in the Justice Department. He is the latest in a series of unorthodox appointments in the Trump era.
Since he was named last week as a temporary replacement for Attorney General Jeff Sessions, Whitaker’s recent background has come under intense scrutiny, particularly his role on the board of an invention-promotion company that was shut down in May after federal regulators accused it of fraud. One White House official acknowledged that Whitaker, who had been Sessions’s chief of staff, received little vetting.
Whitaker declined a request for an interview.
In a statement, Justice Department spokeswoman Kerri Kupec said he underwent “all the usual vetting and procedures” and is qualified for the job. “Acting AG Whitaker has litigated both criminal and civil cases, both as a U.S. Attorney and throughout his years in private practice,” she said.
As acting attorney general, Whitaker presides over federal prosecutors, the FBI, and other Justice Department operations with almost 116,000 employees. He oversees special counsel Robert S. Mueller III’s probe into possible collusion in the 2016 presidential election, an investigation Whitaker has publicly criticized.
Brian Hillebrand, an Iowa banker who became friends with Whitaker after helping to arrange financing for the trailer business, described him as “very intelligent” and driven to succeed.
“Matt is definitely a hard worker,” Hillebrand said. “You definitely want him on your team.”
In the early 1990s, Whitaker was something of a local legend as a tight end on the University of Iowa football team that went to the Rose Bowl. He got an MBA and law degree from the University of Iowa, then worked for a time as general counsel for a Minnesota-based grocery store chain before moving back to Iowa in 2001 and joining a small law firm.
In 2002, he ran as the Republican candidate for state treasurer, positioning himself as a fiscal conservative. He lost by more than 10 percentage points.
That same year, while working at the law firm, he became the majority owner of a manufacturing company that built hauling equipment aimed at farmers and contractors.
“If you want a tough, dependable trailer that will keep pulling long after the others have died, you need a Road Husky!” the company wrote in a promotional brochure.
He sold his share of the company in 2015.
Hillebrand, the banker, said of the business: “It did fine. It was not a huge business.”
In 2003, Whitaker expanded his holdings with the purchase of the day care, Little Endeavors Child Development Center, in his hometown of Ankeny. The center had a capacity for 204 children, state records show.
That year, he and a partner also launched Buy The Yard Concrete, state records show. Whitaker’s four-bedroom home in Urbandale was listed as the headquarters for the company, a two-person firm that serviced projects as far away as Las Vegas, records show.
He was plucked from relative obscurity when President George W. Bush named him to be a U.S. attorney in early 2004. Whitaker had volunteered for Bush’s presidential campaign in 2000 at the local level.
In a disclosure submitted to the federal government for the post, Whitaker was asked to list his most consequential legal work. One case involved personal-injury litigation in which he represented a man whose leg was run over by a car. A second was a contract dispute between a dry cleaner and the grocery store where it operated. In another, he represented a marble and tile company sued by a couple over a home remodeling project.
Whitaker also disclosed the businesses he owned. In handwritten notes, he said he “will terminate upon appointment.” It is not clear from the form what the notation meant.
Kupec, the Justice spokeswoman, said Whitaker complied with ethics advice and resigned from some positions but was not required to sell the businesses.
Whitaker was sworn into office in June 2004.
James Eisenstein, a professor emeritus at Pennsylvania State University who has studied the federal court system, said he knows of no U.S. attorneys with résumés like Whitaker’s.
“This was an extraordinarily weak and unusual background for a U.S. attorney,” he said.
One year into his term, an equipment rental firm sued Whitaker and Buy The Yard Concrete in Nevada, alleging they owed about $12,000 for supplies and equipment rentals, court records show. The lawsuit related to a concrete project in Las Vegas.
Whitaker represented himself in the case, according to court filings. He claimed the rental firm had no right to sue him because he lived in Iowa, noting in one filing that he was the U.S. attorney there.
He also said that the work on behalf of the cement firm was done by contract labor, not company employees, and that he was not involved in overseeing the project.
“If Whitaker did not want to get sued in NEVADA, he should not have conducted business there,” a lawyer for the equipment rental firm wrote in one legal filing. The dispute was settled privately.
Whitaker served as U.S. attorney until 2009.
When he stepped down, he issued a news release that cited several cases as significant, including a prosecution of fraud at a state workforce-training agency, a child pornography investigation that led to charges against 13 people and a crackdown on the misuse of immigrant work visas.
Among the office’s biggest setbacks was the prosecution of Matt McCoy, an openly gay Democratic state senator and a rising political star on the left. A grand jury indictment accused McCoy of using his political position to extort $2,000 from a security firm in Des Moines where he was a consultant.
The investigation took many months but ended with an acquittal in less than two hours, triggering scorching criticism of Whitaker in local media, including questions about whether McCoy was targeted because he was gay and a Democrat.
“Voters and taxpayers deserve to know whether this was just a poorly conceived and badly bungled effort by the government — or whether something else was going on,” a columnist for the Des Moines Register wrote in 2007.
A Justice Department spokesman said Whitaker’s office pursued credible allegations.
Soon after leaving his federal post, Whitaker started a new law firm with two associates in Des Moines. In 2012, he made $79,000 from legal work and had 14 clients, including the National Rifle Association, according to a Federal Election Commission disclosure he made in an unsuccessful bid for U.S. Senate in 2014.
In December 2012, Whitaker, a local photographer and a real estate agent teamed up to rehabilitate a run-down, 22-unit brick apartment building.
The city agreed to give the trio a $165,000 loan, using federal housing funds, in exchange for building affordable units. Once they completed the project — including installing a new roof, boiler and plumbing — they would have to repay only $25,000.
“Little progress was made on the project in 2013 and 2014,” the city told The Washington Post in a statement. “The city communicated with Mr. Whitaker on the urgency of this project.”
After Whitaker’s partners left, he promised to use his own money to finish the project.
On April 1, 2016, the city sent Whitaker a default notice and said the city would “commence legal proceedings” unless he repaid the bulk of the loan within a month, according to the statement.
“The frustrating part was that it appears little progress was made for a couple years under his watch,” Des Moines City Manager Scott Sanders told The Post.
In a letter first obtained by the Associated Press, a city planner wrote that Whitaker’s company “appears to have abandoned the property.”
Kupec, the Justice spokeswoman, said the problems with the project were due to “cost overruns and a bad general contractor.”
In 2016, Whitaker sold his share to Jeffrey Young, a local developer who repaid the loan. Young declined to comment.
By then, Whitaker was expanding his pursuits far beyond Iowa.
He had joined the board of World Patent Marketing, the invention-promotion company in Florida. In August 2015, he sent a threatening email to a client who had complained, noting that he was a former U.S. attorney and writing that “there could be serious civil and criminal consequences for you.”
The Federal Trade Commission last year accused the company of misleading customers and threatening criminal prosecution against dissatisfied clients. In May, the company agreed to pay $25 million and shut its doors as part of a settlement.
Starting in 2014, Whitaker was also leader of a conservative charity, Foundation for Accountability and Civic Trust, a lucrative endeavor that raised his profile in the nation’s capital. Whitaker received a total of more than $650,000 in salary in 2015 and 2016, tax filings show.
Tom Hamburger and Alice Crites contributed to this report.