15 years later, John Middleton is betting that Dave Dombrowski can match Pat Gillick’s success with Phillies | Scott Lauber

After a third consecutive year of flirting with a wild-card spot only to extend one of baseball’s longest active playoff droughts despite carrying a top-five payroll, the Phillies ditched their general manager and handed the keys to a 60-something-year-old executive with two World Series rings.

Dave Dombrowski?

Try Pat Gillick.

Indeed, the Phillies have been in this position in the fairly recent past. And if you don’t think John Middleton recalled the autumn of 2005 as he decided on how to move the organization forward in the winter of 2020, then you don’t know much about the team’s managing partner.

Middleton had not yet risen to that title with the Phillies 15 years ago, but his family did have an ownership stake. Then, as now, he watched with the eye of a successful businessman and the sensibility of a superfan. He was dazzled by Gillick’s bling, the reward for building back-to-back champions with the Toronto Blue Jays, and watched as he maneuvered to bolster the bottom of the roster as well as the top and steer the Phillies to a division title within two years and a World Series triumph within three.

If Gillick were 10 years younger, Middleton might have beseeched him to take the wheel again. But he’s 83 now, happy to be a resource but content, especially in a pandemic world, as a minority shareholder and long-distance adviser.

Dombrowski, persuaded by Middleton this week to run the Phillies’ baseball operations and hired Friday, is basically Gillick 15 years ago. He’s 64, four years younger than Gillick when he came to Philadelphia, with the energy and vigor of hot-shot GMs half his age. Seismic trades and nine-figure free-agent contracts are in Dombrowski’s DNA. And he’s an alpha-male executive, so brazen that he worked without a GM in his final three years as the Boston Red Sox’s president of baseball operations.

» READ MORE: Phillies’ hiring of Dave Dombrowski proof of hope for their 2021 season | Bob Brookover

Oh, he also owns the jewelry that Middleton envies, rings from World Series titles with the Florida Marlins in 1997 and the Red Sox in 2018 and two from American League pennants with the Detroit Tigers in 2006 and 2012.

Surely, Gillick must see the resemblance.

“Yeah, I do,” Gillick said Friday, chortling through the phone. “It’s funny. I kind of bounced around, from Toronto to Baltimore to Seattle, then to Philadelphia. I actually was in Toronto in ’77 and Dave went to work for the White Sox in ’78. I’ve known him and [retired longtime GM] Rollie Hemond since ’78. Dave’s bounced around, too, from Chicago to Montreal to Miami to Detroit to Boston. So we’ve both had kind of similar careers in some ways.”

It’s little wonder, then, that Middleton didn’t take no for a final answer when Dombrowski said in October that he would honor his four-year contract with the group that is trying to bring a major-league team to Nashville, Tenn. He kept checking back but didn’t get traction until this week after Minnesota Twins GM Thad Levine -- Middleton’s preferred candidate over former Miami Marlins president of baseball operations Michael Hill and Los Angeles Dodgers senior vice president Josh Byrnes, according to a source -- withdrew from consideration.

“One thing that the old-school guys -- if you want to say ‘old-school’ -- kind of shake their head at is that it almost seems like experience is a detriment now to getting a position, that basically they don’t want anyone with experience,” Gillick said. “I think it’s important that you have somebody that’s been successful. I could look back 60 years ago. I thought at 21-22 that I knew everything in the world, and then when I got in my 30s, I realized how much I hadn’t experienced.

“I think Dave has the intuition, the instinct, the experience to know where a club is. If a club is close, you put the pieces together. On the other hand, experience allows you to know when you’ve got to hold back and say, ‘This is not the time. We’ve got to get a little more depth in the organization before we decide to go for it.’ I think Dave knows when to play ‘em and when to hold ‘em.”

Dombrowski will make that determination within the next few months after checking under the hood. He isn’t coming here to oversee massive repairs. But he’s likely to find that the Phillies need more than an oil change before riding the carpool lane to their first playoff appearance since 2011.

Even Gillick had to step back before pushing the Phillies forward. Despite inheriting a homegrown core of Jimmy Rollins, Pat Burrell, Chase Utley, Ryan Howard, Ryan Madson, and Cole Hamels (with Shane Victorino and Carlos Ruiz on the way), Gillick dealt Bobby Abreu at his first trade deadline in 2006. It wasn’t until he strengthened the pitching through trades for Jamie Moyer, Brad Lidge, and Joe Blanton (after the additions of Freddy Garcia and Adam Eaton failed) and scooping up unwanted J.C. Romero, Chad Durbin, and Scott Eyre that the Phillies were for real.

Dombrowski’s challenges aren’t dissimilar. Although these Phillies have an expensive nucleus built around free agents (Bryce Harper, Zack Wheeler, Andrew McCutchen), a few scouting/developmental successes (Aaron Nola, Rhys Hoskins, Alec Bohm), a thin farm system, and little payroll flexibility for the blockbusters that Dombrowski loves, the biggest weakness is an alarming lack of pitching depth that will require creativity and keen scouting to fix.

“There will be opportunities on guys that, either he’s injured or had a bad year or some circumstance makes him unattractive to somebody else but in your mind, he’s somebody you want to take a shot on,” Gillick said. “Somebody gave up on Chad Durbin and he got non-tendered. You’ve got to use every way possible to build the nucleus a little more.”

At Middleton’s request, Gillick said he offered “suggestions” about candidates in the Phillies’ search. Middleton got input from other baseball people that he admires, including Terry Ryan, who built contending teams on tight budgets in Minnesota.

Asked in October why he still sought the counsel of team president Andy MacPhail, who oversaw a rebuilding project that didn’t yield a winning season in five years despite a payroll that rose 101.3%, Middleton said: “You do know that he’s won two World Series titles. You do know that Pat Gillick, who’s in the Hall of Fame, has only won three. You know that John Schuerholz, who’s in the Hall of Fame, has only won two [with Kansas City and Atlanta]? Yeah, that’s kind of why I have confidence in him.”

Here’s the thing: Middleton was also describing Dombrowski, the closest thing to Gillick other than Gillick. And in the end, he’s the person Middleton had to have.