Red Sox

Dave Dombrowski is leaving behind a mess for his Red Sox replacement

Dave Dombrowski is leaving behind a mess for his Red Sox replacement

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>>>>>

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MLB Rumors: Yankees offer Gerrit Cole a record contract

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MLB Rumors: Yankees offer Gerrit Cole a record contract

The Boston Red Sox may be looking to cut their payroll this offseason. But that doesn't mean that their rivals will be too.

In fact, some may spend big. And that includes the New York Yankees.

The Yankees have been reportedly interested in free-agent pitcher Gerrit Cole. The former Houston Astro is expected to get a lot of money on the open market, and according to Bob Klapisch of the New York Times, the Yankees have made a record-setting offer for his services.

This would be a big signing for the Yankees, as they could use another top-tier pitcher for their starting rotation. And Cole would certainly fill that need.

Cole, 29, had one of the best seasons of his career for the Astros, logging a 20-5 record and posting a 2.50 ERA. He also struck out a league-best 326 batters and helped the Astros win the American League pennant.

While the Yankees offer is on the table, they are still competing with the Los Angeles Dodgers and the Los Angeles Angels to earn his services, as Klapisch noted. We'll see if this offer is enough or if any of the teams involved in the sweepstakes up the ante.

And while the Yankees chase after Cole, the Red Sox are weighing some moves of their own. According to the latest rumors, they are expressing interest in a reunion with Rick Porcello.

Where Cole ranks among the MLB's top 10 free agent starting pitchers>>>

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MLB Rumors: Red Sox interested in a reunion with Rick Porcello

MLB Rumors: Red Sox interested in a reunion with Rick Porcello

The Boston Red Sox may be trying to cut some payroll this offseason, but that isn't going to stop them from targeting some free agents. And that may include one of their own.

According to Jason Mastrodonato of The Boston Herald, the Red Sox are having talks with Rick Porcello about a potential reunion. While the Red Sox may be interested in Porcello, Mastrodonato wrote that "it's unclear how aggressive the Red Sox will be in their pursuit."

He also noted that a short-term, incentive-based contract may make sense for both sides.

Porcello, soon to be 31, has spent the past five seasons with the Red Sox after being acquired in exchange for Yoenis Cespedes, Alex Wilson, and Gabe Speier. He won the Cy Young Award in his second year with the team, 2016, but he has had issues in the seasons since that campaign.

In 2019, Porcello endured his worst campaign as a pro, logging a career-worst 5.52 ERA and 7.4 K/9, his worst mark since joining the Red Sox. Still, he posted a 14-12 record and still profiles as a solid back-end starter because of his ability to eat innings.

We'll soon see if the Red Sox end up being involved in the Porcello sweepstakes. If they are involved, they will have competition and may find themselves facing off with the likes of the New York Mets, who reportedly have an interest in Porcello.

Where Porcello ranks among the MLB's top 10 free agent starting pitchers>>>

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