None of the owners dissect the payroll or thumb through dog-eared copies of Baseball America at those meetings, which are usually agreeable affairs, and for good reason. In keeping with Philadelphia’s reputation as the biggest small town in America, where everyone knows a guy who knows The Guy, the Phillies’ top brass are an interwoven network of buddies. As a former judge and U.S. Attorney, Mike Stiles seemed like an odd choice to become a senior VP in 2001. In fact, he was a brilliant addition to the corporate roster, thanks to his top-shelf connections among the region’s business, legal and political elite as the team was building Citizens Bank Park. He also shared a room with Montgomery in the Phi Sigma Kappa house at Penn, where Stiles was president and Montgomery was the social chair. There, they partied with an upperclassman named Ed Rendell who would one day join the law firm, Ballard Spahr, that handles the Phillies’ legal work; David L. Cohen, a longtime Rendell confidant, was their attorney for years. The Phillies’ CFO, Clothier, is also a Wharton grad, and met Montgomery thanks to a guy he knew through his daughter’s playgroup — Mike Stiles.
All that familiarity — and the lack of pressure from the people who actually own the team — seems to breed contentment. The front-office turnover rate is amazingly low, despite tales of incompetent employees who appear to get pass after pass. “It’s a very collegial, friendly culture, and sometimes you need a bit of the other kind of medicine,” says a source close to the team. “It’s not a place where a general manager has a bad four-year run and you know he’s going to get fired.”
That’s a nod to Ed Wade, who may be Exhibit A when it comes to the organization’s lack of accountability. Wade started his career as an intern in the team’s public relations department, and eventually rose to assist the general manager. The fact that the team had just one winning season while Wade was in that post didn’t stop Montgomery from naming him GM in 1998. Over the next eight years, Wade compiled a record of zero playoff appearances and an overall winning percentage under .500. His tenure was so abysmal that fans started an online campaign, FireEdWade.com. And Sports Illustrated didn’t just call him a lousy GM — it named its “award” for worst executive in the National League after him. Still, Wade was a “Monty Guy,” and all six people above Montgomery in the Phillies hierarchy — the Phantom Five and Giles — were content to let him keep his job, year after year. A source close to the team says the reluctance to fire Wade — to hold him responsible for the team’s poor performance — is symbolic of what’s wrong with the franchise. “When you don’t win, you make changes, and you make hard calls,” the source says. “When you analyze their changes, they’re pretty soft. If you say ‘Fire those four fucking guys!,’ they say, ‘No, no, no.’ Who is held accountable?” In an organization where friendship is prized more than performance, the answer is … no one.