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The nearly 1,000 pages of search warrant files unsealed today from the Vince Gray investigation likely won’t derail Gray’s run for the Ward 7 D.C. Council seat. Still, the new papers offer a fuller look at the four-year investigation into Gray’s 2010 run and the illicit shadow campaign associated with it.

LL has already discussed some of the revelations in today’s papers. Here are the most significant ones.

Gray May Have Emailed About Some Shadow Campaign Activities

The most significant question of the entire Gray investigation has been whether Gray knew about the shadow campaign activities, and if he did, whether he knew they were illegal. Gray says he’d didn’t; U.S. Attorney Channing Phillips decided there wasn’t enough proof when he closed the case in December without charging Gray. But today’s warrants offer more instances of Gray apparently discussing some shadow campaign activities.

In a search warrant for Gray’s Yahoo email, investigators describe emails where a redacted figure who appears to be Gray discusses how to distribute T-shirts that were later revealed to have been paid for by the shadow campaign. Prophetically, a figure who appears to be Gray writes in an email that one campaign worker should “be careful what information you include in e-mails.”

As investigators closed in, prosecutors claim in the new documents, Gray allegedly met with shadow campaign operative Eugenia Clarke Harris. Harris was so nervous, investigators claim, she wrote Gray a note instead of talking out of fear that they were being recorded. As questions arose about how to explain the shadow campaign activity, Gray allegedly sent Harris an email telling her submit her expenses to the legitimate campaign.

Gray Allegedly Offered Another Candidate Money and a City Job to Leave the Race

Gray’s 2010 run against Adrian Fenty was complicated by Leo Alexander, a second-tier candidate who promised to take some of the anti-Fenty vote. While some details of Gray’s alleged scheme to get Alexander out of the race were already public, an email from Alexander included in today’s files lays it out in detail.

In the email, Alexander complains that Gray promised to back him for a D.C. Council at-large seat, only to switch the deal and offer him a position with the less prestigious Office of Cable Television instead. According to the warrant application, an unnamed figure resembling Gray allegedly authorized his campaign to pay Alexander $20,000, using shadow campaign figure Harris as a cut-out.

“Together we’ll Beat Fenty!” Alexander writes in his email.

Not quite. After Alexander refused the money, Harris sent the money back to the Gray campaign—-an exchange recorded in the District’s Office of Campaign Finance records.

Feds Wanted Email Accounts and Cell Phone Data 

Today’s warrants reveal that investigators filed to search email accounts associated with the campaign, as well as Gray’s own Yahoo email.

Prosecutors also wanted phone information for cooperating suspects. As recently as late year, investigators were trying to obtain cell phone location data for Thompson, Harris, Gray campaign driver Mark Long, and an unnamed fourth campaign figure in the hopes of proving Gray witnessed shadow campaign-related events.

Some Gray Campaign Workers Knew About Illicit Activity

If today’s documents are to be believed, Gray wasn’t the only one aware of some aspects of the shadow campaign. Some members of his campaign were suspicious that something illicit was going on, but didn’t want to be involved.

In one email, one staffer ponders whether shadow campaign operative Vernon Hawkins was up to something. “I’m not in the loop (and don’t want to be)!”  wrote one. One staffer reacted over a Gchat conversation to the prospect of making campaign badges for Hawkins’ workers: “oh fuck me.”

When a man—-apparently Gray driver Long—-showed up at Gray’s campaign with a whopping $100,000 in contributions, even more suspicions were raised about a straw donor scheme. “Lots of checks from out of state,” noted one. “So people were washing money.”

Gray’s Son Could Be the “Close Relative” Mentioned Taking Money

The most intriguing figure in Hawkins’ sentencing memos this week was a “close relative” of Gray. The “close relative” is depicted taking an illicit $10,000 cash payment from Thompson to pay Howard University campaign workers.

Today’s papers offer more details on the Gray relative. He’s described as someone’s son, although no details are offered on who the relative’s father is.

The obvious possibility here is Carlos Gray, Vince Gray’s only son and a volunteer on the campaign. Carlos Gray didn’t respond to LL’s request for comment.

Photo by Darrow Montgomery