Dave Dombrowski built a champion, but he's leaving behind a bit of a mess. Whomever the Red Sox hire to replace him will be staring at the organization's most consequential winter in a decade.
You want a challenge? Try being in charge of the following:
* Mookie Betts will probably be extended or traded this winter, and the latter option no longer feels so far-fetched.
* The starting rotation is anchored by three pitchers Dombrowski signed for more than $400 million, and not one of them is guaranteed to be healthy next season, whether it's Chris Sale, David Price, or Nathan Eovaldi.
* Slugging DH J.D. Martinez could opt out of his contract and force the Red Sox to step up or watch him walk away, though the qualifying offer gives the team some leverage.
* With a payroll pushing $240 million and dead money in the form of Dustin Pedroia's extension, Pablo Sandoval's buyout, and the final year of Rusney Castillo's $72.5 million contract (which doesn't technically count against the luxury tax since he's not on the 40-man roster, but try telling John Henry that $14 million isn't real), the Red Sox will be financially squeezed to address needs in the starting rotation and bullpen, especially if they hope to reset their luxury tax clock and avoid another round of penalties.
* Rafael Devers looks like a superstar in the making, and the Red Sox must decide if they can lock him up to a long-term extension, even though he won't be arbitration eligible for another year.
* Can the team live with Jackie Bradley's inconsistent offense now that he's looking at an eight-figure contract arbitration award? Might outfielder Andrew Benintendi be dangled to acquire young pitching? Is Brandon Workman really a closer, or do the Red Sox need one of those, too?
These complicated issues must be addressed in Dombrowski's wake, and the clock is already ticking.
Because the Red Sox have committed so many resources to an iffy rotation, for instance, there is almost certainly no longer money for both Martinez and Betts. The former will be more affordable because of his age (32), position (DH), and skillset (slugging), but the latter is a younger and more dynamic player.
If Betts is dealt — and that feels increasingly likely, since retaining him will cost at least $300 million — it won't necessarily be because the Red Sox fear losing him, but because they realize they can't afford him. And if that's the case, then you will have lost the defending MVP because of payroll mismanagement.
The rotation serves as ground zero in that regard, since that's where Dombrowski lavished huge deals on Price (7 years, $217 million), Sale (5 years, $145 million), and Eovaldi (4 years, $68 million). Sale has already been shut down, Price will probably soon join him, and Eovaldi just threw five innings for the first time since April elbow surgery.
Because all three are signed through at least 2022 (and Sale through 2024), the problems they pose aren't going away anytime soon, unless Magic Johnson decides to buy another baseball team. That's a massive expenditure for such distressing levels of uncertainty.
Fixing one of baseball's statistically worst rotations won't be accomplished atop the free agent market, where Astros right-hander Gerrit Cole is expected to receive $200 million. There's no way the Red Sox throw such money after yet another 30-something starter.
Acquiring arms behind left-hander Eduardo Rodriguez will require trades, then. Betts is one candidate to be moved, with Benintendi another. The problem is, the Red Sox are so thin in the outfield, dealing any of the current starters will require a parallel move.
Plug one leak, watch another spring.
Likewise, they should prepare to open their checkbooks for Devers, a transcendent talent who is already the best overall hitter on the team, even though he doesn't turn 23 until October. The Braves recently locked up NL MVP candidate Ronald Acuna Jr. for eight years and $100 million, with options that could keep the 21-year-old in Atlanta through age 30. Let the Devers bidding start there.
With Mitch Moreland and Brock Holt on expiring contracts and Michael Chavis limited for now by the hole atop his swing, the Red Sox will need infield help, too, at first and second base. That's a lot of pieces to acquire in one offseason on a limited budget. Bobby Dalbec, anyone?
That's what Dombrowski is leaving behind. His brute-force approach produced a World Series champion, but it also broke a lot of china, and his successor's first order of business will be grabbing a broom.
Dombrowski's worst moves since winning World Series>>>>>
Click here to download the new MyTeams App by NBC Sports! Receive comprehensive coverage of your teams and stream the Celtics easily on your device.