Philadelphia Phillies President of Baseball Operations Dave Dombrowski speaks during the Major League Baseball's general manager meetings, Wednesday, Nov. 8, 2023, in Scottsdale, Ariz. (AP Photo/Matt York)

Phillies President of Baseball Operations Dave Dombrowski got his start as a trade-maker in July 1988, when the Montreal Expos promoted their then-assistant general manager to GM. 

At 31 years old, Dombrowski would be taking over roster decisions from 44-year-old Bill Stoneman, who was known to lament that trades were no longer hashed out over late-night drinks and unrepeatable jokes — the “players” had all these “contracts” with “clauses” that complicated things. Stoneman was adamant about a lot of things, and one of them was that minor leaguers should not be traded away for a “quick fix.” Despite this philosophy in his ear, “Dealin’ Dave” Dombrowski, as he became known, had to try it anyway.

In his second season as VP, Dombrowski sent three Expos prospects to Seattle for difference-making pitcher Mark Langston. Or not: After the Expos failed to make the postseason, Langston tipped his cap and left it in his locker to become a free agent. To make matters worse, the original trade had given up a pitching prospect named Randy Johnson. 

So, the following year, Dombrowski learned his lesson and made the same deal — but in reverse. Montreal received three prospects from the Pirates in return for impending free agent Zane Smith. Those three prospects were Moises Alou, Willie Greene, and Scott Ruskin, who would go on to play a combined 30 years in the major leagues, Alou as a six-time All-Star. 

From then on, Dombrowski knew how he wanted to make a deal: Boldly. Directly. As soon as possible. 

Decades later, and the Phillies boss is still “Dealin’.” 

When the Phils needed a shortstop, Dombrowski signed the best one on the market in Trea Turner, and did it so fast that it’s possible he sprung out from behind a potted plant in the 2022 Winter Meetings hotel lobby with the contract in his hands. This off-season at the prematurely-ended GM Meetings, we just listened to Dombrowski clear up one of the winter’s biggest Phillies questions with a series of emotionally challenging but pretty direct information: 

Bryce Harper will play first, Kyle Schwarber will be the DH, and Rhys Hoskins is, in all likelihood, out of a job

A tough pill for some, but wrapped in as much cheese Dombrowski could, and forced down Philadelphia’s throat. Has he always been this up-front and efficient? Let’s take a look at a few of his other major deals as an executive to see. 

Gotcha by a dollar

In early 1990, Tim Burke was considered the Expos’ best pitcher out of the pen, but by the end of May, it would’ve been generous to say so. He’d allowed runs in his first three appearances of the year and always seemed good for a couple of opposing base runners at the worst possible time.

He was doing it again on May 30 when he allowed four hits, a walk, and two runs. Then, in the bottom of the ninth, Burke cracked his fibula jogging over to cover first base. 

Into his role stepped Dave Schmidt, a pitcher Dombrowski and the Expos had targeted the previous winter. A free agent left to dangle by the Orioles, Schmidt had a simple philosophy for getting paid: More, please. Whatever he’d gotten from a previous deal, he wanted the amount to increase in his next one, apparently even though he’d finished 1989 with a 5.69 ERA. 

It was a bold move, but Dombrowski went for it. Schmidt had made $650,000 with the Orioles in 1989. So, to get him to pitch for Montreal in 1990, Dombrowski offered Schmidt $650,001. The price was right and Schmidt signed with the Expos.

Now here he was, available to take over late-inning relief duties because he’d been acquired the past winter and didn’t have a hairline fracture anywhere in his leg. Schmidt would have a 2.38 ERA in June after taking over for Burke and be named the Expos’ Player of the Month. All because — well, because of a lot of things, but partially because Dombrowski had heard a pitcher he was targeting had wanted more… and offered exactly that.

It was satisfying not only because Schmidt had thrived when an opportunity to play a bigger role had emerged, but because directness had not paid off for Dombrowski elsewhere in the winter of 1990. 

Free agent Kirk Gibson had been offered a deal from the Expos for two years and $4.2 million. It came with geographical convenience (Gibson could easily travel home to Michigan) and a spot in the middle of the batting order. Dombrowski seemed proud they had checked all the boxes they could, but Gibson instead elected to go with the Royals’ offer of two years, $3.3 million with a chance to earn another million in incentives. 

“Extremely disappointed,” Dombrowski said. Truthfully, it was a bit ridiculous. A big-name free agent? Going to Kansas City? That’s disappointing for everyone. 

A dynamic duo

By 1993, the Marlins had popped up in South Florida and Dombrowski’s work in Montreal earned him the position as their inaugural GM. They proceeded to notch a losing record every season for the next four years. 

Before the 1997 season, it was time for Dombrowski and the Marlins to hire a new skipper. It just so happened that Jim Leyland was done in Pittsburgh, though the 53-year-old’s $1 million contract was supposed to last through 2000. Leyland had left in disgust due to ownership’s lack of desire to spend and win. 

The race was on. Every team in need of a manager, and maybe some that just wanted Leyland, began the courtship process. 

But Dombrowski had an inside track: he and Leyland had worked together on the White Sox years before, and Marlins ownership had agreed to put up a sweet offer to the right man for the job. Or at least, whoever Dombrowski told them was the right man for the job. 

So Leyland rejoined Dombrowski in Miami and they immediately — immediately! — won the 1997 World Series together. It was a pairing that would return, on other teams. 

“There’s no denying how well the Dombrowski-Leyland partnership works,” wrote one Marlins columnist in 2011, when the pair had reunited again, this time with the Tigers, who were in the middle of a deep playoff run yet again. “There’s the 1997 championship as proof, plus the Tigers’ spot in the 2006 World Series as substantiation. Now, they’re back in the ALCS.”

Getting past the LCS 

Likely looking for revenge for making him look foolish during the whole Gibson affair, Dombrowski had joined the Detroit Tigers in 2002, hoping to exact terror on a fellow AL Central squad, the Royals. 

Tigers owner Mike Illitch had been “desperate” to return his team to glory, and he hired Dombrowski as the architect. Three years into his tenure, Dombrowski had a list for what the team needed to reach the level both he and ownership sought: A better bullpen, a big middle of the order bat, and top tier starting pitcher. 

If that sounds like every team ever’s shopping list, well, fair enough. But the difference was, Dombrowski went down his list and got everything he wanted: Troy Percival improved the bullpen, and Magglio Ordóñez powered up the order.

Did it work? Not quite. Percival finished with a 5.76 ERA and the Tigers were 20 games under .500. But the acquisition of Ordóñez still looked good in 2006, when he was one of the Tigers’ four 20-home run hitters, and Dombrowski checked off that last item on his list, the starting pitcher, in Kenny Rogers. He also added future Hall of Fame catcher Iván Rodríguez.

The 2006 Tigers were suddenly a 95-win team that plowed through the Yankees and A’s on their way to the World Series — one of four ALCS appearances they’d make during his time with the organization.

A crucial part of Dombrowski’s success in his pre-Philadelphia days was the desire of the owner to get his team to stop embarrassing itself, which led to spending, which led to a higher quality of free agents being signed, which led to better on-field results.

Another defining characteristic — at least of his time in Detroit, where he spent 14 years — was that his teams made it to the LCS multiple times and couldn’t finish the job, similar to a certain Philadelphia-based ball club the last two seasons. 

So is it a flaw that Dombrowski gravitates toward great players who flame out over the course of a season? Or is the whole point of roster construction to give yourself the best possible chance to win it all on paper before you let the chaos of baseball take over on the field?

Ready for the next ring?

Well, Dombrowski does have two World Series championships separated by over 20 years. So it’s not that he never builds a team that can get there.

The second one came in 2018 with the Red Sox, after Dombrowski had traded four prospects (and agreed to cover the $25 million on his deal) for Craig Kimbrel, signed 30-year-old David Price to a seven-year deal, acquired a knife-wielding Chris Sale, and brought in Arizona slugger J.D. Martinez, all over the course of three years. Sometimes, the direct moves you make today pay off indirectly years later. Not sure if you still get credit for them, but the numbers are there. 

You could also argue that Dombrowski’s previous satisfaction with Kimbrel is what made him interesting enough to bring to Philadelphia, where Kimbrel blew Games 3 and 4 of this season’s NLCS. 

Oops! I let the darkness get in.  

As the already impactful 2023 off-season goes on for the Phillies, Dombrowski will obviously be its protagonist. He’s got the team where he wants it — despite our shared disappointment, the Phillies have been fun to watch over two consecutive deep postseason campaigns. But now there’s all the fiddling to do necessitated by contracts, free agency, and a greater knowledge of where the flaws exist. 

Rumors of Dombrowski being open to a Nick Castellanos trade were killed, but a move like that, while a bummer on some levels, would liberate the Phillies’ batting order from one of its chronic free-swingers — the plate approach that became their undoing in the NLCS. 

Several aspects of Dombrowski’s likely Hall of Fame career have paid off well for him: He’s benefitted from his boss’ desire to win, from a close relationship with his manager, from moving swiftly and efficiently when he knows what he wants. It feels clear he values people, going back to the same players or organizations with whom he’s built relationships in a 45-year career as a baseball executive. There have been countless other moves, big and small, not mentioned here. 

It was ultimately Dombrowski’s decision to move on from Rhys Hoskins, but he’s not the one who sniped Hoskins in the leg last spring.

According to Dombrowski, the hard part’s over — he’s got all the backing he needs from owner John Middleton. Now he just needs that third ring. Hopefully, he’s not waiting 20 more years.

Justin Klugh has been a Phillies fan since Mariano Duncan's Mother's Day grand slam. He is a columnist and features writer for Baseball Prospectus, and has written for The Inquirer, Baltimore Magazine,...