The Phillies are Dave Dombrowski's 5th World Series team. Should more teams play his version of Moneyball?

The task of building a World Series team has changed dramatically from 1997 to 2006 to 2012 to 2018 to 2022, but two things have remained true: It’s incredibly hard, and Dave Dombrowski has managed to do it anyway.

As Game 3 brings Philadelphia its first taste of the World Series since 2009, you’ll see the factoid that the Phillies president of baseball operations is now the first executive to lead four different franchises to the pennant. You might miss that he was already the only one to do it with three. But when we look back in 10, 20 years, maybe when Dombrowski is inducted to the Hall of Fame, what might be even more striking than his track record of success is that in the GM-centric era ushered in by “Moneyball” and Billy Beane, Dombrowski has twice been fired despite it all.

Recently, he has often been viewed as an “old school” point of comparison, a one-man referendum on the ways baseball teams are or are not being built.

From the spark of baseball’s information age to its spiraling acceleration beyond the spectrum of the casual fan’s eye in recent seasons, the concepts at the heart of “Moneyball” — and the terms it ushered into the sports lexicon — have become both ingrained, flattened, dressed up as a bogeyman and stripped of all meaning by decades of inane crosstalk.

It’s worth remembering the simple idea that started it all: Seek out advantages that are undervalued by the bulk of the competition. Moneyball, as defined by economists after seeing it in action for years, is “buying assets that are undervalued by other teams and selling ones that are overvalued by other teams.”

And when you look at it that way, a surprising conclusion emerges: Dave Dombrowski, in many ways, represents a Moneyball for 2022 baseball.

Phillies executive Dave Dombrowski, seen here after winning the NLCS, has brought his trademark win-now mentality to Philadelphia at the behest of team owner John Middleton (right). (Photo by Michael Reaves/Getty Images)
Phillies executive Dave Dombrowski, seen here after winning the NLCS, has brought his trademark win-now mentality to Philadelphia at the behest of team owner John Middleton (right). (Photo by Michael Reaves/Getty Images) (Michael Reaves via Getty Images)

What going against the grain means now in MLB

First, let’s talk about “Moneyball.”

Michael Lewis’s 2003 book documenting Beane’s purposeful zigs with the Oakland Athletics glorified and reshaped the job of running a baseball front office. With Beane’s successful strategies elucidated and validated, the previously underground sabermetric movement of quantifying player performance and value rapidly took root everywhere, even with teams not operating on Oakland’s shoestring budget.

There are two levels to the lasting ripple effects that we still summarily call Moneyball, and they are important to distinguish.

On a practical baseball decision-making level, Beane’s central insight held that quantitative analysis should be used in addition to the qualitative recommendations of scouts to evaluate players and field the best team. There’s still a push-pull to find the right balance, but this is now just common sense.

On a higher level that reaches beyond the GM job and into the ownership suite, “Moneyball” unleashed an obsession with efficiency.

There’s a whole separate (and interesting) conversation to be had about the ways the new information led to a more stagnant, homogenous game on the field. But that was mostly an accidental snowball effect of many people attempting to do their jobs while the overarching governing body (MLB) failed, until recently, to use the same data to create protective guardrails.

On that higher plane, the effects were more intentional. Team owners gravitated toward strategies that allowed them to spend smaller and smaller portions of their vast fortunes and revenue streams while still selling fans on the idea that they were trying as hard as they could to win the World Series. They cultivated the idea that big contracts for star players could be harmful, and should be avoided in many cases. They coined and championed new buzzwordy holy grails for roster construction: Financial flexibility and sustainability.

Dombrowski’s status as a baseball establishment staple makes him easy to typecast. Emphatically silver-haired, he memorably towered over teams that predate the Moneyball revolution. So when the Red Sox hired Dombrowski in 2015, much was made of team owner John Henry’s comments that the team had developed “too much reliance” on analytics.

In reality, Dombrowski found the department lacking and oversaw an expansion of that operation in addition to the more outwardly apparent expansion of the player payroll. The result, in 2018, was the most successful team in the storied history of the Red Sox — probably the most successful team of the 21st century thus far. Less than a year later, Henry abruptly fired Dombrowski and introduced his successor, Tampa Bay Rays alum Chaim Bloom, by essentially announcing a desire to fall in line with his cost-conscious brethren.

“He possesses the essential qualities to establish a sustainable baseball operation throughout the organization,” the press release said, attributing the comment to chairman Tom Werner, “with an emphasis on long-term success at the major league level.”

The intervening seasons have lent clarification to that corporate-speak: Dombrowski was fired on a hair trigger as the league’s top payroll sputtered to 84 wins. Two of Bloom’s three teams have finished dead last in the AL East, but they have been cheaper. So he’s still in charge.

Dombrowski represents Phillies' refreshing ambition

You can find a “new Moneyball” in almost every good team, a tactic or player preference they have leaned into that has led to wins. I’ve done it myself! But what Dombrowski represents is less a novel or innovative scheme to win baseball games and more a (relative) purity of approach.

The vast majority of MLB teams in 2022 are playing Sustainaball, and the Phillies are doing something else — something that, ironically, might be more aptly dubbed Moneyball.

One of the main pieces of information that makes efficiency and sustainability look like particularly appealing qualities for a baseball team is the randomness of the postseason. Whether we like it or not, American sports award championships via tournaments, not the more telling regular season results, and baseball’s playoff outcomes are particularly divorced from its endless summer trials.

Building an organization that consistently spits out teams good enough to earn a roll of the dice, the logic goes, is your best shot at winning the ultimate prize.

The Phillies tried something like that with a day-late, dollar-short rebuild, and failed. By the time team owner John Middleton demoted former GM Matt Klentak and convinced Dombrowski to come aboard, the team was already pulling from the Dombrowski playbook. Klentak signed Bryce Harper to a 13-year, $330 million deal and traded for J.T. Realmuto, a rare superstar-level catcher, trying to get the team over the hump.

Dombrowski is the guy you bring in to shoot the moon, to take big risks in hopes of reaping big rewards. This season’s team also includes several big-money deals inked by Dombrowski, including Kyle Schwarber and Nick Castellanos.

His moves have not all been successful, far from it. Castellanos had his worst season ever at the plate. Closer Corey Knebel was stressfully inconsistent, then injured. He bought a bill of goods from Texas when he dealt for Kyle Gibson in 2021.

But with Middleton’s support, Dombrowski errs on the side of ambition, not frugality. In Boston, he was fired over an 84-win season and replaced by a regime that traded away Mookie Betts when he didn’t agree to a below-market extension. In Philadelphia, he followed a disappointing below-.500 season by locking Realmuto up to a long-term deal.

They ranked fourth in payroll in 2022, and perhaps more tellingly, have the second-most money already committed for the 2023 season, same for the 2025 season.

Whether you want your team to employ Dombrowski is almost a philosophical matter, one I'm guessing no one in Philadelphia will be fretting over as they flock to Citizens Bank Park this week. But it's worth thinking deeply about before accepting a team owner's assertions that the best path forward involves underwhelming offseasons and the exits of beloved stars, and before we write off the Phillies as aberrations of one hot October. At least one other team — the San Diego Padres club that the Phillies dispatched in the NLCS — has veered toward the starry-eyed, present-over-future approach with similar highs and lows.

Dombrowski-style teams, which tend to be top-heavy, will almost always have regular season bust potential. What he works at is building a potent critical mass, the sort that can feel unbeatable in the exhilarating but impossible-to-gauge small sample theater we use to name a champion. This Phillies team didn’t achieve it until they cycled through a bevy of center fielders, shortstops and relief pitchers, until they fired Joe Girardi and promoted Rob Thomson, but they achieved it.

Everyone remembers the famous Billy Beane line, that his “s*** doesn’t work in the playoffs.”

Dave Dombrowski’s does. Whether it proves as influential — like whether the Phillies are good in 2025 — is a question for a different day.