Gillespie, a former head of both the Republican National Committee and the Virginia GOP, served as McDonnell's campaign chairman during his 2009 run and was a senior adviser during his transition into office.
Now that he's challenging Sen. Mark WarnerMark Robert WarnerFive Senate Democrats reportedly opposed to Biden banking nominee The Hill's Morning Report - Presented by ExxonMobil - House to vote on Biden social spending bill after McCarthy delay Overnight Defense & National Security — Presented by Boeing — US mulls Afghan evacuees' future MORE (D-Va.), Democrats see his connections to the embattled former governor as yet another hit on Gillespie's lobbying record and ties to political influence.
"Ed Gillespie raised millions of dollars in soft money for Bob McDonnell's campaigns for attorney general and governor, and he's the poster child for the sometimes questionable intersection of politics and influence," Democratic Senatorial Campaign Committee spokesman Matt Canter tells The Hill. "Gillespie needs to answer for his considerable political and fundraising support for Bob McDonnell."
A federal grand jury indicted McDonnell and his wife on Tuesday for illegally accepting expensive gifts, large loans, luxury vacations and expensive gifts from a businessman and prominent political donor. McDonnell says he made a mistake by accepting the gifts but defiantly declared he's broken no laws in a Tuesday press conference.
Gillespie expressed sympathy for McDonnell following the indictment, but like many other GOP politicians close to the former Virginia governor, stopped short of supporting his family, as they now face a bevy of criminal charges that could put them behind bars for years.
"I was deeply saddened to hear today’s news concerning my friends Bob and Maureen McDonnell," he said in a Tuesday statement to The Hill. "Governor McDonnell has been a dedicated public servant, and he and Maureen are in my prayers as they endure a very painful time in their lives."
Democrats are looking to paint Gillespie as a corrupt political insider, and they've already gone on the attack against the former lobbyist for advising Enron, the defunct energy company.
Republicans are also beginning to worry the attacks might stick against the new GOP candidate and admit the timing of the McConnell news doesn't help Gillespie's nascent campaign.
"It plays exactly into the 'fixer' narrative Democrats are pushing — 'Republicans aren't as honest as they sell themselves to be.' They're going to try to say Gillespie is cut from the same cloth as Bob McDonnell," said GOP strategist Ford O'Connell, who has worked on a number of Virginia races.
Gillespie has so far focused on Warner's support of ObamaCare in his attacks.
His campaign released a Web video titled "Who was right?" featuring clips of Gillespie criticizing ObamaCare, as Warner defended it before the bill passed. The video finishes with text saying Warner "broke his word to Virginians" that they could keep their healthcare plans.
— This post was updated at 12:10 p.m.