It's amazing to read this profile of Middleton which is only six years old. He's become what he beheld
Herb and John pulled the trigger in ’93 — 15 percent of the team for $18 million — and John got heavily involved. The owners met four times a year, and the role as head of the board rotated among them, until it was John’s turn to preside. Nobody wanted to replace him; he was a dog with a rag. Fellow owner Michael Betz, who recently sold his 10 percent share to John and the Buck cousins, says Middleton was obsessed with changing the team’s direction. Nothing was too large or small, “including where we were buying chairs for the boardroom.” He calls John’s drive and ability to gather data “terrifying.” Betz means that as a compliment: “I remember my first aha! moment with John. We were sitting around the boardroom, and John said, ‘In order to analyze something, you need to be able to measure it.’ That’s quite a statement, if you look at it.” Middleton constantly cornered Betz with his complaints and ideas, about the business operation, the team itself, Giles, anything. “The team was run in an old-time-baseball style,” Betz says. “Scouts would stand around and talk about whether a batter’s hands dropped before he swung the bat. But I don’t think John had any answers. I don’t think anyone did.” The Phillies, after all, were the losingest sports franchise ever for a reason, a tanker that had been chugging in one direction for a long time.
The biggest stumbling block was the terrible financial deal the team had with city over Veterans Stadium. And through that long losing period at the end of last century, the moribund owners made no cash calls to sign better players or revamp the farm system. The Middletons reportedly railed behind the scenes for Giles’s ouster, though John will only admit now to believing Giles had grown a bit old and tired by the mid-’90s. The board promoted Giles’s assistant, David Montgomery, to team president in 1997. There still seemed to be no answers....
Montgomery’s demotion — he now represents the team in league matters and in the community — is trickier to parse. He got jaw cancer in 2014, just as Middleton’s frustration with his management was ratcheting up, and as he was pushing into his late 60s. Montgomery’s friend Mike Tollin, a sports filmmaker who grew up in Havertown, calls the demotion a “bloodless coup.” It was handled with kid gloves, and Middleton is careful now to praise Montgomery for his great warmth and service to the team. But the real answer to what had to happen lies in an order of priorities. In Montgomery’s office in Clearwater in late March, I ask him which is more important: an organization where loyalty reigns supreme, including to the players who brought the team a championship, or winning. Montgomery answers by raising his hands from his desk to hold them flat before me at the same level: One hand represents loyalty, the other winning. They bob in tandem. Neither is superior.
Middleton maintains no such parallels in his thinking. He believes loyalty is a good thing, but he has no doubt, as an owner of the Phillies, as the new face of the team, about his primary responsibility: “When you’re running a baseball team, it has to be winning.”