... Wow. His focus on the Virginia 2007 Elections lasted until.... the primaries?
Despite serving as RNC Chairman -- and then championing Harriet Miers' nomination -- Gillespie has remained popular among grassroots conservatives (Not Larry Sabato is not a conservative, but I think he has hit on the angst that some VA conservatives may feel). Gillespie, however, is now coming very close to "jumping the shark," and becoming strictly a "party guy."
Should he choose to leave his post as VA GOP Chairman (a position he has only held for about six months), Gillespie would be in danger of angering VA grassroots conservatives -- and closing the door on a future in Virginia. (Some have speculated that Gillespie's election to VA GOP Chairman was either ,1. A way to keep his friend, George Allen, in the game, or 2. A way for Gillespie to prepare for his own Senate campaign.)
On the other hand, who could blame Gillespie for considering the option? Despite fundraising success, this WaPost story from Saturday underscores the mess the VA GOP is in right now. And just Saturday, the VA GOP nominated the controversial Faisal Gill as their nominee for a State Delegate seat in Northern Virginia.
... And, let's be honest, the opportunity to be a senior advisor to a president (even if it's this president), doesn't come around every day. It would be tempting for most political operatives.
My advice would be to stay put. No matter how tempting or flattering the offer, Gillespie already has Bush credentials. And staying put would show character and commitment.