It’s a simple question: other than the candidate — who has a day job, after all — who is running Attorney General Tom Reilly’s campaign for governor?
The answer is surprisingly elusive. Sometimes it’s everybody. Sometimes it’s nobody.
“One of the questions everyone asks is, ‘Who’s the go-to, day-to-day person helping Reilly with his decisions?’” says one astute Democrat. “Is there somebody who’s both serving as his consigliore and helping with field operations? It’s just very unclear.”
“In Deval’s campaign, it’s very clear that John Walsh is in charge,” adds a second Democratic observer, referring to the campaign manager for Deval Patrick, Reilly’s sole declared opponent in the Democratic primary. “In the Reilly campaign, I don’t think anyone’s in charge. And that’s a formula for disaster.”
This ambiguity seems only fitting. With the primary six and a half months away, Reilly is a deeply compromised figure: a tough guy who seems fragile, a political veteran who’s oddly naive, a onetime front-runner who’s looking like a loser. But Reilly also has far more money than Patrick; a deep knowledge of state politics that Patrick can only hope to approximate; high name recognition; and a cadre of committed supporters whose faith remains unshaken. He has also suffered the harshest scrutiny imaginable and managed to survive — which, to take a Nietzschean tack, should toughen him up for the campaign to come.
The truth is, Reilly could still be the Democratic nominee. For that to happen, though, he’ll need to do everything right in the coming months. Fixing the dysfunctional mechanics of his campaign would be a good place to start.
A gaggle of operatives
Based on conversations with several veteran Democratic observers, it appears that there’s no Karl Rove–esque figure coordinating Reilly’s campaign from week to week. Instead, what the candidate seems to have is an assortment of competing power centers. One group is made up of young operatives from the AG’s office and the Reilly campaign. They include Steve Kerrigan, the AG’s former chief of staff [see "Correction," below]; David Guarino, the former Herald reporter who was hired as the AG’s communications director last year; Corey Welford, the former AG spokesman who now functions in the same role for the campaign; and Steve Bilafer, another former chief of staff for Reilly.
Sean Sinclair — who’s Reilly’s titular campaign manager, although he seems to have far less influence than this title would suggest — also belongs in this group. Sinclair’s résumé features some impressive highlights: he managed Nevada senator Harry Reid’s re-election campaign in 2004; and he ran the successful gubernatorial campaign of Ted Kulongoski, an attorney general who was elected governor of Oregon in 2002. His knowledge of Massachusetts is minimal, however, and his ties to Reilly are relatively shallow. According to one reliable source, Sinclair played no role in the disastrous selection of state representative Marie St. Fleur as Reilly’s running mate last month. (St. Fleur quit after her checkered financial past became public knowledge.)
When major decisions loom, this group takes on a few extra members. They include Neil Oxman, a Philadelphia-based media consultant who helped Pennsylvania governor Ed Rendell win re-election in 2002; Massachusetts congressman Marty Meehan; and Will Keyser, director of corporate communications at the Boston PR firm Hill Holliday.
Reilly and Meehan, now co-chair of Reilly’s campaign, go way back. When Reilly was Middlesex County district attorney, Meehan was his first assistant. Reilly’s connection with Keyser, meanwhile, is an extension of his friendship with Meehan. In 1998, when Reilly faced tough opposition from state senator Lois Pines in his quest to jump from Middlesex DA to the AG’s office, Keyser left his post as Meehan’s chief of staff to serve as Reilly’s campaign manager. When Reilly prevailed after an especially bitter primary battle with Pines, Keyser received a good deal of the credit.
Then there are his friends
Two ex–chiefs of staff [see "Correction," below]; a campaign manager and an ex–campaign manager; overlap between the AG’s office and the campaign; a cadre of advisers who drop in for the big decisions — all that’s confusing enough. But the picture gets even murkier.
For starters, there are the assistant attorneys general who work in Reilly’s office. Several have been with Reilly since his days in Middlesex County, which leads one political observer to suggest that Reilly’s closest friends in this group constitute — at the very least — another cadre of de facto campaign councilors.