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The Trump campaign’s new chief of staff was arrested and charged with campaign finance violations in 2016

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  • Stephanie Alexander was named chief of staff of Donald Trump’s re-election campaign on Tuesday.
  • In 2016, Alexander — then named Stephanie Milligan — was arrested in Oklahoma and charged with conspiracy to violate state campaign finance laws. The charges were later dropped, and the case was expunged last month at Alexander’s request.
  • Prosecutors claimed that Milligan and several alleged co-conspirators illegally coordinated the efforts of a “dark money” independent group with the campaign of a GOP candidate for Oklahoma superintendent of public instruction.
  • The case relied in part on texts and emails recovered from Alexander’s then-boyfriend, Chad Alexander, who was arrested for possession of cocaine in 2014, according to court records. The two are now married.  Chad Alexander filed for bankruptcy in November, listing Stephanie as a “co-debtor.” He owed more than $250,000 to the IRS.
  • Prosecutors dropped the case against Stephanie without explanation in 2017, saying that the investigation would continue.
  • The Trump campaign says Alexander is “a campaign professional and continues to be a valued member of the team.”
  • Visit Business Insider’s homepage for more stories.

The newly promoted chief of staff for Donald Trump’s presidential campaign was arrested in Oklahoma in 2016 and charged with conspiracy to violate state election laws after police seized her then-boyfriend’s phone in a cocaine bust, Insider has learned.

Stephanie Alexander, previously the Trump campaign’s Midwest political director, was bumped up to chief of staff Tuesday in a campaign shake-up. Prior to joining the Trump campaign, Alexander was active in state GOP politics in Oklahoma, where charges filed in 2016 allege that she participated in a conspiracy to illegally coordinate dark money in a 2014 race for state superintendent of public instruction.

Alexander pleaded not guilty, and the state dropped the charges in 2017 without explanation. Last month, a state judge granted Alexander’s request to both expunge and seal the court records on the case.

Asked for comment about the four-year old case, Trump campaign spokeswoman Erin Perrine defended the president’s new 2020 chief of staff. “Stephanie Alexander is a campaign professional and continues to be a valued member of the team,” she said.

The 2014 state superintendent race pitted two Republicans against each other in the primary: challenger Joy Hoffmeister and incumbent Janet Barresi. Alexander and her boyfriend at the time, political consultant Chad Alexander — the pair have since married — both worked to establish a purportedly independent advocacy organization called Oklahomans for Public School Excellence that raised money from anonymous donors and ran a $300,000 ad barrage attacking Barresi during the campaign.

But according to a criminal information filed against Alexander and four alleged co-conspirators just days before the 2016 presidential election by the office of Oklahoma County District Attorney David Prater, OPSE was a front organization designed to conceal “a conspiracy to commit campaign contribution violations and illegal coordination” between Hoffmeister and dark-money donors.

It is illegal in Oklahoma for donors to give more than $5,000 to a campaign, and independent groups that raise larger amounts are barred from coordinating with campaigns.

The information, which used Alexander’s name at the time, Stephanie Milligan, cited text messages and emails in accusing Alexander, Hoffmeister, and others of secretly coordinating OPSE’s activities with the Hoffmeister campaign.

Chad Alexander

Chad Alexander, an Oklahoma political consultant, was arrested for possession of cocaine in 2014, leading investigators to evidence they would use against his then-girlfriend, Stephanie Milligan.

Oklahoma County District Attorney


State prosecutors got a break in the case in May 2014 when Chad Alexander, who previously served as chairman of the Oklahoma Republican Party, was arrested on a cocaine possession charge while driving his Mercedes in Oklahoma City. Police seized his cell phones and computer, and found texts and emails showing communications between Alexander, Hofmeister, and others allegedly plotting a dark money strategy to run ads against Barresi.

After the cocaine arrest, Stephanie Alexander took over Chad Alexander’s role at OPSE. Hofmeister won the election.

Chad Alexander later pleaded guilty to felony cocaine possession. He did not respond to messages seeking comment.

At the time of her arrest in November 2016, Stephanie Alexander was already serving as a battleground campaign official on the Trump presidential campaign. According to court records, Alexander refused to sit for an interview with investigators but offered to answer written questions from the state prosecutors. 

She faced up to 10 years in jail on three felony counts. But David Prater, the district attorney, abruptly withdrew all charges in the case in August 2017.

At the time, Prater told local news outlets that the case was not over, and that the charges had only been withdrawn temporarily “pending further investigation.”

“We’re not done,” he told the web site NonDoc. “We’ve had information come to us over the last several months regarding one or more of the defendants that we need to follow up on before we take the case to preliminary hearing.” 

But the case was never re-filed.

A spokesman for Prater did not immediately respond to a request for comment.

Gary Eastland, who was the chief investigator on the Hofmeister-Alexander case in Prater’s office, said in an interview he remains befuddled why the charges were never refiled.

“That’s a damn good question,” said Eastland, who retired from the district attorney’s office in April 2017 about four months before the state filed for the case to be dismissed. “I have my suspicions.”

Alexander was a “co-debtor” in her husband’s recent bankruptcy, which erased more than $250,000 in debt to the IRS

The Hofmeister affair wasn’t the only time that Chad and Stephanie Alexander ended up in court: Chad Alexander filed for bankruptcy in Oklahoma in November 2019, court record show. Stephanie Alexander is listed in filings as a “co-debtor.” Among the debts that were discharged when Alexander exited bankruptcy in March of this year: $262,576 in unpaid taxes to the IRS, and $50,406 in unpaid taxes to the Oklahoma Tax Commission.

Alexander’s promotion on the Trump campaign came as part of a wider realignment of key staffers working to win four more years for the president. Effective Tuesday, Bill Stepien, a former White House political director, became deputy campaign manager, while Alexander took on the role of chief of staff.

A press release from Trump’s re-election team announcing the job changes noted Alexander’s experience as Midwest regional political director for Trump Victory, a joint operation between the president’s campaign and the Republican National Committee. It also referenced her work as a GOP consultant and fundraiser to both state and federal candidates, as well as corporations, nonprofits and political action committees.

Alexander cited her role as a member of the president’s political efforts “since the beginning” and highlighted the 2020 effort than includes a thousand paid staffers and more than 1 million trained volunteers.

“I am proud,” she said, “to take a larger role in that machine.”

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