Tom Lindenfeld (left) with Michael Brown in 2007
Tom Lindenfeld (left) with Michael Brown in 2007 Credit: Photograph by Darrow Montgomery

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For nearly two decades, it’s been hard not to find political consultant Tom Lindenfeld involved in some campaign in the District. Lindenfeld engineered Adrian Fenty‘s rise to the mayoralty, then groused about his one-time patron after his 2010 loss.

Lindenfeld has also been helping Fenty protege Muriel Bowser during her own mayoral run, with his political consulting firm receiving $105,937.69 from her campaign so far.

But an unnamed person resembling Lindenfeld has allegedly been up to some much less savory campaigning in Philadelphia, according to documents recently filed in federal court. The pseudonymous “Person B”—-described by the Philadelphia Inquirer and Philadelphia Daily News as Lindenfeld—-stands accused in an elaborate scheme to secure an illegal mayoral campaign loan, then pay it back with federal grant money.

Lindenfeld, who didn’t immediately respond to LL’s request for comment, has worked for scores of District politicians, becoming a fixture in local campaigns along the way. A Washington Post profile of him before Bowser’s primary win described him as “generously profane” and “a favorite of reporters.”

Update, 4:50 p.m: Bowser says she’s cut ties with Lindenfeld. “Tom is well-known for working on national and local elections, including as a consultant on my council races and in my most recent primary campaign,” Bowser says in a statement emailed to LL. “I’m quite surprised by the allegations out of Philadelphia today. I have the highest expectations of transparency from my campaign team; Tom no longer has a role on the campaign. We are entirely focused on working together with D.C. residents on the big issues that will shape our collective future.”

The case centers on Pennsylvania Democratic Rep. Chaka Fattah‘s unsuccessful run for mayor of Philadelphia in 2007, with the person resembling Lindenfeld surfacing in a recent guilty plea from Fattah advisor Greg Naylor. In Naylor’s plea, prosecutors describe how “Person B” allegedly used his company to spend illicit loan money for Fattah’s unsuccessful bid, then received a contract funded by federal grant money to pay the loan back.

Naylor’s guilty plea paints “Person B” as an integral part of the scheme. As the unnamed political consultant resembling Lindenfeld allegedly wrote in an email as he tried to secure money to pay back the loan, “I have a lot on the line.”

In April 2007, with Fattah’s campaign running low on money, the person resembling Lindenfeld allegedly agreed to receive a $1 million loan from a supporter of Fatah’s. Then, according to the plea, Naylor and “Person B”—-described as a “founder and partner in a Washington, D.C. political consulting firm”—-spent $600,000 to boost Fattah’s chances, including $200,000 on “walking around money.” Naylor’s plea describes “Person B” telling him to fake an invoice to cover up the expenses.

It didn’t work. After Fattah lost, the consultant resembling Lindenfeld allegedly paid back $400,000 to the unnamed Fattah backer.

But there was still the issue of the outstanding $600,000. After the election, Fattah’s once-generous backer fell on hard times and demanded the money back through “Person B,” according to Naylor’s plea.

The alleged plan to pay back Fattah’s benefactor involved taking money from Sallie Mae that was intended to be used to put on an education conference, according to the plea. A nonprofit with the money allegedly contracted with another firm, which then made a contract to send the money to the political strategy firm that resembles Lindenfeld’s LSG Strategies.

When the pass-through company’s chief financial officer asked why his company, which had its own money issues, was agreeing to a contract with a political firm, he was allegedly told that the contract would give them “influence and political connections.”

But the alleged scheme, worked on in January 2008, didn’t go smoothly. As the other company struggled to raise enough money to send to the company that the Philly media claims resembles Lindenfeld’s, “Person B” sent the angry email where he claimed he had a lot on the line. In the email, subject line “You are killing me,” the writer urged the person who hadn’t sent the money not to drag it out.

Apparently, it worked. On Jan. 31, 2008, according to the plea, the $600,000 was sent to the District-based political firm, then wired from there to the unnamed benefactor believed to have helped Fattah. The plea notes that the District political firm never did the work that it had been hired to do by the company that sent it $600,000.

Photo by Darrow Montgomery