WHEN NEWS BROKE last November that Middleton had sold his family cigar company to the Altria Group, owners of Phillip Morris, for $2.9 billion in cash, there seemed a glimmer of hope that finally someone in the Phillies’ Phantom Five had the capital, cojones and, most important, business instincts to build a winner. Middleton splits his time between a Bryn Mawr manse and a beachfront house in Stone Harbor, and is known as the most fiercely private — and privately passionate about the team — of all the partners. “[Herb] Middleton was the most outspoken owner,” says Lee Thomas, the Phillies’ general manager from 1988 to 1997. “When he died [in 1998], his son took the ball. They’re not what you’d call baseball people, but they were the most focused on the team and most willing to make things happen.”
Montgomery denies a long-circulating rumor that John Middleton was the force behind the $85 million acquisition of Jim Thome in 2002, the boldest Phillies signing in at least a decade. The legend goes that as the owners fretted over the size of Thome’s salary, Middleton declared, “I’ll pay for him myself!” There’s also talk that Middleton pushed to recruit cannon-armed Billy Wagner, the most reliable closer in the Phillies’ inconsistent bullpen in recent years. (Shortly after hightailing it to the Mets for more money, Wagner joined former Phils Curt Schilling and Scott Rolen in questioning the ownership’s will to win.) John Kruk, ESPN analyst and a leader of the pennant-winning 1993 Phillies, believes both Middleton tales. “He’s very aggressive,” Kruk says. “From what I understand, he had to be talked off the ledge a few times. He wanted to be like the Yankees and buy everyone, and the other owners said whoa, hold on.”
Middleton’s fingerprints were also said to be on the body of general manager Ed Wade, whom Montgomery begrudgingly axed after eight years of failure, and it’s believed the Middletons accelerated Montgomery’s ascension by nudging Giles into retirement. “If there was anything in the group that pushed him out, that’s my guess,” says a team insider. “They were always sniping at him. They would either buy into [the criticism of Giles] or start it.” One thing the Middletons and Giles seemed to agree on was the value of a championship. In 2006, Giles told a group of reporters, “The ownership group’s main goal is to win. Win a World Series. Particularly, two of them say in every meeting, ‘Gosh darn it, I want to win a World Series.’” Giles then admitted he was one of the two, prompting a reporter to ask, “Is the guy who pushed you out [Middleton] the other one?” Giles replied, “No comment.”
Those who know Middleton outside of the team suggest he’s not interested in a bigger stake, and if one is up for grabs — say, Betz’s share — the other owners are entitled to a portion of it, too. Still, Middleton’s windfall is the stuff Phillies fans’ dreams are made of. “Out of all of them — the Buck brothers, Betz — he would be the one to stir the pot,” says Kruk. “I got into an elevator with him at the Vet after someone just blew a save. He said, ‘If I have to get a whole new damn bullpen, that’s what I’ll do.’ He was trembling.”
The reality is more sobering. Since turning into one of America’s richest men, Middleton has become even more private, and more unlikely than ever to raise his profile. There’s also a structural hurdle in his way — flooding the team with cigar money would undermine the group dynamic that Giles designed and Montgomery upholds. If Middleton somehow claimed a majority stake, he could do more than fume over blown saves and his co-owners’ timid caution — he could tell Montgomery what to do, or fire him. But that’s not how the business of the Phillies is built. For all his frustration at losing, Middleton can’t — and, ironically, because of his newfound fortune, won’t — do anything about it.
IN A TOWN where sports owners’ larger-than-life personas define their teams — Ed “No More Superstars” Snider and Jeff “Gold Standard” Lurie — the Phillies’ stewards are simply tone-deaf. When the Flyers spoiled their 40th anniversary season last year by setting a franchise record for losses, Snider didn’t hide behind publicists or his front office. He faced TV cameras and spoke to reporters. His pain was palpable. He hurt like you did, and goddamn it, he would do something about it. Snider wasn’t pleased with his Sixers, either. He made tough calls, firing two of his beloved GMs, and this year, both teams made it back to the playoffs. As for the Eagles, one thing Jeff Lurie will never be accused of is humility, and there’s a swagger to his franchise.