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: Mookie Betts, Red Sox had massive gap in 2019 contract talks

MLB Rumors: Mookie Betts, Red Sox had massive gap in 2019 contract talks

If you ask Lou Merloni, there's a reason the Boston Red Sox are actively looking to trade Mookie Betts before the season begins.

The Red Sox avoided arbitration with Betts settling on a one-year, $27 million contract with the outfielder earlier this month.

But that's after Boston failed on several occasions to sign Betts to a long-term contract before he becomes an unrestricted free agent in 2021.

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According to Merloni, the two sides weren't even close.

The former Red Sox infielder reported Tuesday on WEEI's "Ordway, Merloni & Fauria" that Boston offered Betts a 10-year, $300 million contract extension following the 2018 season. Betts countered with 12 years and $420 million, according to Merloni, and the deal fell through.

That gap of $120 million marked the third consecutive offseason the Red Sox and Betts were off by roughly $100 million in contract negotiations, citing the eight-year, $200 million offer Betts rejected following the 2017 season and the five-year, $100 million deal he turned down after the 2016 season.

Merloni added he's unsure whether the Red Sox made another offer to Betts this offseason -- but the fact that they're discussing a Betts trade with the likes of the San Diego Padres and Los Angeles Dodgers should answer that question.

"They can't get it done," Merloni said on WEEI. "They know they can't get it done. When you go to a guy for three years in a row and you're off by almost $100 million -- in one instance over $100 million -- they know they can't sign him."

The 12-year, $420 offer Betts reportedly seeks is in line with recent major league megadeals: Slightly south of Mike Trout's 12-year, $430 million behemoth but north of Bryce Harper's 13-year, $330 million deal.

Boston reportedly was unwilling to shell out that kind of cash for Betts -- and may lose the former American League MVP because of it.

If Plan A was keeping Mookie Betts, it feels like Red Sox are moving to Plan B

If Plan A was keeping Mookie Betts, it feels like Red Sox are moving to Plan B

When Red Sox ownership finally addressed Dave Dombrowski's dismissal in late September, chairman Tom Werner made what remains the most honest and revealing assessment of the team's approach to superstar Mookie Betts.

"We've stated publicly that we would hope he would stay with us the rest of his career," Werner said. "We have made proposals to him in the past and he did want to test free agency, which is his right. And we'll have some conversations with him going forward. But obviously there'll be a point where hopefully we can make a deal or we'll decide at that point what is plan B or plan C, but we haven't gotten to that point and we're very open to continuing discussions with him."

Based on the recent reports out of San Diego, in particular, it sure feels momentum is building towards a plan B or C that end with Betts's departure.

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Multiple factors have led to this point.

The first is ownership's stated goal (NOT A MANDATE, STOP CALLING IT THAT!) to drop below the $208 million luxury tax threshold. The team's offseason of inactivity may have lulled us into thinking that John Henry and Co. had changed their minds, but all the reasons that desire made sense in September still apply now. Resetting their tax penalties will put the team in the best long-term position to build a winner, with or without Betts.

Then there's the shape of this offseason itself.

December hit us with a flurry of high-end activity, but virtually all of it was of the free agent variety, from Stephen Strasburg to Gerrit Cole to Anthony Rendon. Outside of former Cy Young winner Corey Kluber being dealt to the Rangers, most of December's 13 trades were relatively minor.

Monday's move of All-Star Starling Marte from Pittsburgh to Arizona suggests the start of a late trade season, since the recent signings of Nick Castellanos (Reds) and Josh Donaldson (Twins) means the free-agent market is pretty much dry. "The pace of this offseason has been unusual around the industry, in terms of when things evolved," allowed Red Sox chief baseball officer Chaim Bloom recently.

Then there's the sign-stealing elephant in the room, which is the loss of manager Alex Cora and MLB's investigation into the 2018 champions, a dual catastrophe that leaves the Red Sox in danger of losing draft picks at precisely the moment when their thin farm system most needs them.

If Betts is their best avenue to acquiring young talent, and if the talks to extend him (Plan A) have convinced management that he's definitely hitting free agency, which means he's almost definitely gone, then it would be a dereliction of duty not to explore every possible avenue for maximizing his value.

After a quiet winter in that regard, rumors are suddenly percolating like steam-forced espresso. The Red Sox and Padres have reportedly progressed far enough to haggle over how much of Wil Myers' remaining $61 million the Red Sox will assume, with at least one young outfielder and pitcher joining him in return.

Meanwhile, San Diego's division rivals in Los Angeles loom with a potential second Boston bailout, especially if they're willing to take on both Betts ($27 million) and David Price ($32 million) and really clear the books for 2020, just as they did with Adrian Gonzalez and Co. in 2012.

That's two motivated buyers and one motivated seller potentially transitioning to Plan B. That sounds like a recipe for a deal, which means Red Sox fans should prepare to kiss their MVP right fielder goodbye.

Sometimes your primary plan just doesn't play out, so you move on to the next one.