To your first question: yes. To your second: not so much.
Keep in mind that Thompson—a reclusive D.C. businessman who is at the center of the federal investigation into what prosecutors say was an illegal shadow campaign to help Vince Gray get elected as mayor in 2010—hasn’t been charged with any wrongdoing. The FBI raided his home and offices in 2011, and one of his associates, Jeanne Clark Harris, pleaded guilty to fraud related to the Gray campaign last summer, saying she took money from an unnamed businessman (who people familiar with the case say is Thompson) to pay for $650,000 in campaign-related expenses. Harris also said she helped conceal that businessman’s campaign donations through a straw-donor scheme.
Had Thompson started a PAC, he could have donated huge sums of his own money to help Gray get elected. It’s not an uncommon idea. In 2010, developer Don Peebles put nearly $100,000 into a PAC whose purpose was to attack Adrian Fenty, Gray’s opponent, for allegedly turning his back on poor black people. Peebles’ name is there in public campaign finance reports for all to see, though, a level of disclosure Thompson might have been eager to avoid: During a court appearance, Harris said Thompson was concerned about his city contracts should Fenty get re-elected.
But a PAC’s activities would be far more limited than the shadow campaign’s. PACs cannot legally coordinate with campaigns. So the things Thompson allegedly paid for, like Gray’s personal chauffeur, would have been verboten.