Published Oct. 21, 2018

It’s tempting to think that David Dombrowski has been chasing a white whale ever since he’s been a baseball executive.

It’s tempting to construct a narrative that here he is again, in the World Series, knocking at the proverbial door—a door that he’s been unable to kick down.

It’s tempting to look at the roster that Dombrowski has cobbled together as the man running the Boston Red Sox, see all of the former Tigers dotting it, and say that he’s merely trying to accomplish in Beantown that he couldn’t get done in Motown.

It’s tempting to assess Dombrowski’s style of front office management with the Red Sox and deduce that here we go again, with he tearing another farm system apart in order to acquire the high profile, high octane, ready-to-go talent needed for a deep playoff run—and that while it didn’t quite work with the Tigers, maybe he can close the deal in Boston.

These would all be neatly packaged storylines, if it wasn’t for that World Series that Dombrowski won back in 1997 while in charge of the Florida Marlins.

Another era, another type of game

If it seems as if that was a different, bygone era of baseball, it was.

Analytics were discussed in private sector boardrooms, not in dugouts. Home runs and RBI still meant something. Starting pitchers completed games now and again. WAR was something engaged in on battlefields, not on ball diamonds.

But Dombrowski has his brass ring, even if it was won against a baseball landscape that is foreign to what we’re used to today. And that’s why it seems as if he still hasn’t won one at all.

It seems like it in Detroit, especially.

Dombrowski joined the Tigers in November 2001 as team president and within five months he had canned the GM and the manager—both on the same day.

That purge was a dramatic beginning to a nearly 15-year run with the Tigers, one filled with exciting free agent signings, blockbuster trades and tantalizingly close brushes with greatness.

High risk, low return in Detroit

The Tigers won a lot under Dombrowski’s watch, but they could never win the big one. And in his pursuit of a championship, Dombrowski cashiered one prospect after another, gutting the organization’s feeder system, in order to bring in the star power that made Comerica Park the place to be on summer nights in Detroit.

The Tigers, with Dombrowski running the show, were a lot like the Red Wings, who considered no youngster untouchable when it came to acquiring seasoned, star NHL players.

It worked at Joe Louis Arena, to the tune of four Stanley Cups in 11 years.

With the Tigers, not so much—even though Octobers were quite memorable at Brush and Madison.

Dombrowski is at it again, in Boston.

He’s back in the World Series, for the fourth time. His last two journeys there, with the Tigers (2006, 2012), ended with a thud. The Tigers went 1-8 in those two Fall Classics.

Wayne Huizenga: no Ilitch, he

The 1997 championship with the Marlins was not only a long time ago, and accomplished when baseball was a much different game than it is now, it was under odd ownership.

Almost immediately after the champagne dried in the locker room, Marlins owner and former Blockbuster Video chief Wayne Huizenga ordered that Dombrowski tear the roster apart (“I really didn’t think he was going to do it,” Dombrowski said), requiring salaries to be dumped like yesterday’s trash in order to mitigate what Huizenga claimed was a $34 million loss in 1997. In 1998, the Marlins, while Dombrowski and field manager Jim Leyland watched helplessly, plummeted to 54 wins after accumulating 92 the year prior.

There was no such self-destruction in Detroit, until literally the waning hours of Dombrowski’s tenure, in late-July, 2015.

A parting gift in Detroit

Just before being canned by Tigers, Dombrowski engineered trades that sent stars David Price and Yoenis Cespedes packing (plus reliever Joakim Soria), with the team receiving Matt Boyd, Daniel Norris, JaCoby Jones and Michael Fulmer in return.

The Tigers were big time players in free agency for most of Dombrowski’s time in Detroit. No check was too big for owner Mike Ilitch to cut. No contract was albatross enough in specter.

It didn’t work. The Tigers were kings of the AL Central, but beyond that, the postseason was a minefield. Gut-wrenching failures were as prevalent as the thrills of victory.

The Red Sox knew what they were getting

Dombrowski has his Red Sox, in his third full season on the job, in the World Series. Neither he nor the franchise are strangers to this moment. The Red Sox have captured three rings since 2004.

The Red Sox have paid the price for David Dombrowski’s kind of success, as the Tigers did. The Red Sox farm system isn’t thought of very highly by folks who follow those sorts of things.

But that’s how Dombrowski does things. The Red Sox fully knew that when they hired him just weeks after the Tigers gave him the ziggy.

The Red Sox hired Dombrowski with the expressed belief that he was the executive best equipped to replicate Ben Cherington and Theo Epstein’s championship work.

Three years and some change later, Dombrowski has gotten the Red Sox back to where they’ve been accustomed since 2004. It’s important to note that the Red Sox haven’t lost a World Series since 1986.

Does the HOF beckon?

There’s some scuttlebutt that Dombrowski is headed to Cooperstown—especially if the Red Sox take care of the Dodgers in this year’s World Series.

“There’s very few executives that get multiple opportunities to [win a World Series],” says longtime friend and current assistant with the Red Sox, Frank Wren. “But Dave’s been one of the best general managers in the game for a long, long time.”

We’ve seen this movie in Detroit before: bargain away young chips, acquire big name guys, make the playoffs, advance to a World Series here and there.

But with the Tigers, those World Series appearances were embarrassing in their brevity. In both cases, the team that was on center stage resembled very little the one that had gotten through the earlier playoff rounds—despite all the star power.

It’s highly unlikely that this Red Sox team will crap the bed against the Dodgers. In fact, I’m not anticipating much of a Series.

If the Red Sox win, all the usual farm system gutting that Dombrowski is famous for, will be forgiven. If they lose, it will be a third straight failure in the Fall Classic for DD—but the first in 32 years for the Red Sox franchise.

It’s an interesting stake.