Philadelphia Phillies Owners: The Phantom Five

The Phillies may finally be serious ­contenders, but the franchise is still the losingest in sports history. For that we can blame a group of people we never see and never hear: the team’s (very) silent owners

Earlier at the Diamond Club party, Giles stood alone in a corner. He laughed quietly to himself when Rollins cracked a joke, and was careful to let Montgomery stand in the spotlight alone. When asked about his fellow owners, Giles’s grin disappeared. “I’ll talk to you about anything,” he said politely, “but the ownership group.”

DAVE MONTGOMERY SITS in a pristine meeting room inside the corporate offices of Citizens Bank Park, telling tales of bygone Phillies teams. The former Phillies ticket salesman still scores each game by hand. Today he’s brought pencils and a yellow legal pad to take notes, even though he’s the one being interviewed about the team’s leadership. That was the intention, at least. Wearing a V-neck sweater, quick with a warm laugh that narrows his eyes to a close, Montgomery is, by all accounts, a gentleman in a game of tobacco spit and head-first slides in the dirt. He’s also a politician, filibustering his way around direct questions about the owners he protects year after year. Asked if he’s made a conscious decision to be less outspoken than Giles, his predecessor, Montgomery says, “I just believe the organization needs an image that’s not directly tied to wins and losses.”

Dave Montgomery is a mild-mannered guy, but it’s hard to imagine a more radical statement. After all, what we’re talking about here isn’t your kid’s tee-ball league or your niece’s Division III volleyball program. This is professional sports, where athletes are paid tens of millions of dollars to perform, and where loyal fans invest their time, money and passion in a team with one singular hope: to see them become champions. If this isn’t about wins and losses, then what exactly is it about?

That attitude — winning would be nice — has infected the Phillies organization for decades now. And it trickles down from the very top, from the owners themselves.

The Phantom Five meet four times a year, beginning in March during spring training. That session is known as the annual meeting, and it’s a chance for the Phillies vice presidents and Montgomery to deliver state-of-the-team reports to the bigwigs. Bill Webb, the attorney who helped Giles buy the team more than a quarter-century ago, is still there, handling the minutes. The meeting leads off with Montgomery’s baseball report, recapping the past season, laying out an improvement plan for the one ahead, and answering the sorts of questions the average fan might ask. (How’s our top 2006 draft pick doing after Tommy John surgery? Is there another Kyle Kendrick in the farm system?) The other executive reports — like the economic breakdown from Jerry Clothier, the team’s finance guru since 1982 — rarely generate further discussion. There’s another meeting after the draft in June, and a light December session that doubles as a holiday party. The season-end recap is scheduled each year for September, as if to presume the Phillies’ campaign will never extend into October.