Dave Dombrowski’s ambitious goal for the Phillies: Balance winning it all with sustained success for years

Dombrowski had a reputation for going all in on winning a championship, perhaps at the expense of long-term contention. But with the Phillies, it’s clear he is aiming to do both.

Dave Dombrowski, right, with John Middleton, wants to put the Phillies in position to have as many chances at a World Series as possible.Read moreHeather Khalifa / Staff Photographer

by Scott Lauber

Published Dec. 20, 2024, 5:00 a.m. ET

In November 2005, on his first day as general manager of the Phillies, Pat Gillick sat down to lunch with David Montgomery and John Middleton in the executive dining room at Citizens Bank Park.

“I’m sure you’ve got questions,” Gillick told his new bosses. “Fire away.”

Middleton went first: “What’s it take to win a World Series title?”

Said Gillick, architect of back-to-back champs in Toronto: “Luck.”

Middleton retells the story often, mostly because of how unsatisfying he found Gillick’s answer. It would be 10 years before Middleton became the frontman of the Phillies’ band of owners. But then, as now, he was as much a fan as financier, and what fan, especially in Philadelphia, accepts the idea that a championship is the product of mere serendipity?

So, Middleton asked Gillick to explain, and, well, let him take it from here.

“I said, ‘I get luck in a lot of phases in my life. I don’t know exactly how you think luck plays in a World Series title,’” Middleton said. “He said, ‘Well, John, good organizations consistently produce good teams that compete for and often get in the playoffs. But the difference between getting in the playoffs and winning the World Series is luck.

“‘Because, to win the World Series, you have to have 25 healthy guys who are playing well at precisely the right moment in time. You can look at almost every season and there is a team that, if the season stopped in July and they had the World Series, a different team would win the World Series than the team that ultimately won it.’”

And if that was the case in 2005, when eight teams made the playoffs, it’s even truer now that the field has swelled to 12 clubs. In the last 20 years, eight wild cards and eight teams with baseball’s best regular-season record won the World Series. The Phillies were champions with 92 wins in 2008 but didn’t even get there after 97- and 102-win seasons in 2010 and 2011. They raised the pennant as an 87-win wild card in 2022 and fell in the divisional round this year as a 95-win NL East champion.

Consider it all proof that getting inside the door matters more than how you punch your ticket.

The goal, then, is to get as many kicks at the postseason can as possible. The Dodgers have made the playoffs 12 years in a row but won only two World Series, one in the 60-game COVID-19 season in 2020 and the other this year after back-to-back divisional-round disappointments. The Red Sox also won two titles in 12 years but made the playoffs as often as they finished in last place (five times).

Which would you rather be?

Most modern baseball executives talk more about sustainability — a word Gillick might have chosen if it were en vogue at the time — than going all-in on a championship window. Dave Dombrowski came to the Phillies a few years ago with a reputation for prioritizing the latter, perhaps at the expense of the former.

In Philadelphia, likely the final stop on his road to joining Gillick in the Hall of Fame, it’s clear that the 68-year-old president of baseball operations is aiming to do both.

Since taking charge of the Phillies’ baseball operations in the 2020-21 offseason, Dombrowski has worked on parallel tracks. On one side, he built around an existing core of Bryce Harper, Zack Wheeler, and Aaron Nola by shelling out Middleton’s cash to keep J.T. Realmuto and sign Kyle Schwarber, Nick Castellanos, Trea Turner, Taijuan Walker, and others. On the other, he hired Preston Mattingly to revamp the infrastructure of a bone-dry farm system that was slowly being replenished by inherited scouting director Brian Barber.

The tracks converged in July when the Phillies were open to trading any prospect other than Andrew Painter for White Sox lefty Garrett Crochet. It would have been seen as classic Dombrowski, a go-for-it deal to push a win-now team into the end zone. But a trade didn’t come together.

When the teams picked up talks last month, it seemed likely Dombrowski would jump again. This time, though, Crochet would have been available to the Phillies for only two playoff runs, not three. So, although the payroll is pushing $300 million and the star-laden core is on the other side of 30, Dombrowski passed.

“I’ve been there before, done it before,” Dombrowski said last week after the Red Sox coughed up four prospects, including two of Baseball America’s top 100, for Crochet. “Not sure it was the right time for us to do that right now.”

(Maybe not. Just in case, let’s circle back in a year or two and weigh Crochet’s value against the Phillies’ top prospects, notably infielder Aidan Miller and center fielder Justin Crawford.)

Don’t misunderstand, though: The Phillies are as all-in as ever on winning it all. Middleton still wants his [doggone] trophy back. But they had what many rival talent evaluators considered the most complete roster in baseball this year and got bounced from the playoffs earlier than the previous two postseasons.

It feels reminiscent of Dombrowski’s teams from a decade ago in Detroit. Justin Verlander and Max Scherzer sat atop the rotation; Miguel Cabrera, Victor Martinez, Prince Fielder, and later Torii Hunter and Ian Kinsler anchored the lineup. Dombrowski pushed his chips closer to the middle of the table each year with win-now moves (see: Shane Greene-for-Robbie Ray; Alfredo Simón-for-Eugenio Suárez; David Price-for-Willy Adames/Drew Smyly in a three-team deadline deal).

But the Tigers went from losing in the World Series in 2012 to falling in the AL Championship Series in ‘13 and the divisional round in ‘14 to missing the playoffs in ‘15. Dombrowski was let go, and they didn’t reach the postseason again until (checks notes) this year.

The moral of the story: If you aren’t careful, the window can slam shut.

Dombrowski, under contract through 2027, pushes back on the notion of a finite contention window and instead outlines a more ambitious goal: building an organization that can sustain success over more than a handful of years. In other words, doing what he couldn’t in Detroit and wasn’t given the chance to see through in Boston after three consecutive division titles and a World Series triumph in 2018.

The Dodgers did it with a combination of big-budget moves, such as trading for and signing Mookie Betts and signing Shohei Ohtani and stockpiling talent within the organization. The Phillies are striving to mimic that balance. So, if Painter, Crawford, and Miller aren’t being turned into two seasons of Crochet or one year of Kyle Tucker, it’s imperative that they’re part of the Phillies’ core through the latter half of the decade.

“I think people, when they say ‘championship window,’ [they mean] with maybe this one group of players,” Dombrowski said recently. “That’s significantly different than being in a championship window, period. Maybe you have a down year mixed in somewhere because something happens, but you try to [contend] on a yearly basis. That’s the challenge of a good organization.

“Look at the Dodgers, right? They’ve been there for how many years? The Braves have been there how many years? That should ultimately be your goal, and that’s what you’re trying to accomplish.”

And the more postseason shots that an organization shoots, the better its chances of eventually having the good fortune of breaking through as a World Series champion.

“I was with the clubs in Detroit that had three future Hall of Famers on it and a lot of star players and won our division almost every year, and we never won the World Series,” Dombrowski said. “It’s hard to win. There’s a lot of good clubs out there, so you just have to be the club playing the best at the right time and maybe get a break or two there.

“But sometimes you’ve got to be careful. Because in Boston, we were there 2016, we won our division; 2017, we won our division. We lost both times in the first round. We go, ‘Son of a gun, we’ve got a really good team.’ And we won the whole thing the next year after that in 2018. Sometimes you just play a little better, you get on a roll, you do the right things. That’s what makes winning feel so good because it’s so hard.”

So random, too, at least once October comes around.