Nathan Eovaldi

Say goodbye to J.D. and Mookie? Red Sox payroll decisions are about to get ugly

Say goodbye to J.D. and Mookie? Red Sox payroll decisions are about to get ugly

If Red Sox ownership really wants to reset the luxury-tax clock, then the new GM should expect the following item to be missing from his new office: a checkbook.

For the Red Sox actually to drop below the $208 million threshold that returns their penalty structure to zero will require not so much pruning shears as a chainsaw, with two high-profile victims -- Mookie Betts and J.D. Martinez -- on the chopping block.

The Red Sox spent more than $240 million last year and will be in that range again this year. If they spend beyond the tax threshold again in 2020, they'll trigger the most onerous penalties, with a tax of 50 percent on every dollar spent over $208 million, 95 percent on every dollar over $248 million, and a sliding scale in between. They could end up making a tax payment of more than $20 million.

The problem with dropping below that $208 million figure is the Red Sox are already well over it for 2020 if they do nothing except keep their signed and arbitration-eligible players. By just a simple back-of-the-envelope calculation, they have more than $220 million already committed to next year's team, which is why Dave Dombrowski's successor will inherit such a challenge.

The clearest way to slip below that threshold requires a pair of unthinkable moves -- letting Martinez opt out of his contract and walk, and trading Betts. And even that might not be enough, given the rest of the team's needs.

Those two should count for roughly $50 million against next year's cap, assuming Betts earns about $28 million in arbitration and Martinez carries his $22 million luxury-tax hit (on an actual salary closer to $24 million). Renouncing Martinez would still cost $6 million for cap purposes in 2020, since it's the difference between his tax hit ($44 million) and his actual earnings ($47.5 million in salary, $2.5 million buyout) over two years in Boston.

If that's where ownership wants to maroon its new GM, John Henry and Co. might as well hire Harry Sinden, who took arrows for the Jacobs family while holding a death grip on the Bruins' purse strings in the 1980s and early '90s.

How did the Red Sox find themselves in such dire financial shape following a season that will see them miss the playoffs and finish around .500? It's not pretty.

Consider the following 2020 salaries, totaling nearly $135 million, for luxury tax purposes:

David Price ($31 million), Martinez ($22 million), Chris Sale ($25.6 million), Nathan Eovaldi ($17 million), Dustin Pedroia ($13.75 million), Xander Bogaerts ($20 million), Christian Vazquez ($4.5 million).

If we estimate $60 million in arbitration (which requires saying goodbye to backup catcher Sandy Leon and knuckleballer Steven Wright), we're already pushing $200 million with just the following players: Betts, Jackie Bradley, Eduardo Rodriguez, Andrew Benintendi, Brandon Workman, Heath Hembree, Matt Barnes.

Add young, pre-arb players like Rafael Devers (whom we'll get to in a second) and Michael Chavis, plus $15 million for medical expenses and benefits, and we're already in the $220 million range without addressing free agent losses such as Rick Porcello, Mitch Moreland, and Brock Holt, or depth for a rotation that doesn't know if it can trust Sale, Price, and/or Eovaldi to stay healthy, even though they'll be earning $79 million in real money.

Removing Betts and Martinez from the equation drops that commitment to the $175 million range, but also creates holes at DH and right field that can't be filled for free.

It also calls into question whether it makes much business sense, in 2020, to extend Devers, since doing so will jump his tax number from about $800,000 to $12 million to $15 million if he were to receive a contract in line with the eight-year, $100 million extension Ronald Acuna Jr. signed with the Braves.

This is all assuming that ownership has designs on dropping below $208 million. If it does, there's no way the Red Sox will pay Betts $35 million a year, and you can kiss him goodbye. There's also no realistic path to squeezing in Martinez at $25 million annually. That's what happens when an unreliable Big Three is soaking up a third of the payroll. The prospects of moving Sale, Price, or Eovaldi without eating most of the money range from dim to hopeless.

With payroll and winning no longer strongly correlated -- if the season ended today, two of the game's six lowest payrolls would face off in the AL wild-card game (Tampa vs. Oakland) -- the Red Sox can't simply buy their way to a title.

So, good luck to the new guy if he's ordered to shed payroll, because that's going to cost him some serious talent and leave the Red Sox in a position that might benefit their bottom line and long-range plans, but could make 2020 every bit as painful as 2019.

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Three deals that illustrate where Dave Dombrowski ultimately went wrong in eyes of Red Sox ownership

Three deals that illustrate where Dave Dombrowski ultimately went wrong in eyes of Red Sox ownership

Here's the thing about Dave Dombrowski's "worst" deals -- they almost always landed impact players.

When he overpaid for closer Craig Kimbrel, in his first major acquisition as Red Sox president of baseball operations, he still landed an All-Star. When he took the David Price bidding into the stratosphere in what became the highest contract ever given to a pitcher, he still landed the de facto 2018 postseason MVP. When he surrendered promising left-hander Jalen Beeks to the Rays, he still landed eventual playoff hero Nathan Eovaldi.

But those deals still took a toll on the long-term health of the organization, and it's worth exploring how they came to be viewed by ownership as signals that Dombrowski wasn't the right man to lead the baseball operation moving forward, which is why he was fired on Sunday night.

Start with Kimbrel. Dombrowski acquired the All-Star closer from the Padres on Nov. 13, 2015, by making what became his signature -- the offer you can't refuse. The trade created a ripple of uneasiness across a front office that had grown accustomed to the hoarding of prospects by predecessor Ben Cherington, even as it recognized the need to ease up on the reins.

At issue: the centerpieces of the trade -- outfielder Manuel Margot and infielder Javier Guerra -- represented a fair price on their own to acquire the disgruntled closer, who hadn't thrived in San Diego after five years of dominance in Atlanta. Each was a consensus top-60 prospect, with Baseball Prospectus ranking Margot 14th following the 2015 season.
Dombrowski is a man of action, however, and he wanted the deal done, so he sweetened the pot with left-hander Logan Allen, a teenager who had just posted a 1.11 ERA in his pro debut while walking only one batter in 24.1 innings.

While Kimbrel certainly produced in Boston, making three All-Star teams and saving more than 100 games, the loss of Allen proved costly this July when the Indians made him a central figure in the three-way trade that sent right-hander Trevor Bauer to Cincinnati, top prospect Taylor Trammell to the Padres, and Allen and slugger Franmil Reyes to the Tribe.

Allen debuted this season at 22 and is exactly the kind of cost-controlled piece the Red Sox could use to augment a rotation that's underperforming and overpaid.

Speaking of the rotation, Dombrowski has committed more than $400 million to three giant question marks -- Price, Chris Sale, and Eovaldi. When the Red Sox signed Price for a record $217 million a month after acquiring Kimbrel, they didn't just surpass the next-highest offer, they obliterated it. The runner-up Cardinals reportedly offered Price a seven-year deal in the $175 million range. The Red Sox blew that number out of the water to overcome whatever misgivings Price may have harbored about pitching in Boston, which probably should've been a red flag. As the Globe's Alex Speier noted, they effectively bid against themselves. Now his contract looks unmovable.

Then there's Eovaldi. This was an under-the-radar moment, but many in the organization felt he could be acquired without surrendering Beeks, a hard-throwing left-hander who had impressed in an emergency start against Team USA before the 2017 World Baseball Classic, when he struck out Christian Yelich and Adam Jones in two scoreless innings.

Beeks had a number of advocates on the player development side who recognized his potential to develop into a big league starter, especially after he overhauled his arsenal to feature a 95 mph four-seam fastball and cutter.

It's easy to look at that deal and say, "Eovaldi was instrumental in winning a World Series. Who cares that you gave up Jalen Beeks?" But what if the Red Sox could've acquired Eovaldi for a lesser prospect -- and with Eovaldi coming off yet another arm surgery, his market wasn't exactly robust -- and kept Beeks?

He'd be another depth option in an organization that badly needs it. Instead, he has emerged as a key multi-inning arm in Kevin Cash's bullpen, with an 11-3 record since arriving in Tampa.

The same can be said of Giants right-hander Shaun Anderson, a 2016 third-round pick shipped to San Francisco in 2017 for Eduardo Nunez. Anderson has made 16 starts in the big leagues (albeit with a 5.22 ERA) and owns a higher ceiling than the pitchers the Red Sox were forced to throw in the 4-5 spots of the rotation this season.

Meanwhile, how much could the bullpen use someone like Ty Buttrey? The 6-foot-6 right-hander had some command issues early in his minor league career, but since going to the Angels last July for second baseman Ian Kinsler, has averaged nearly 11 strikeouts per nine innings while posting a 3.90 ERA. That's a solid setup man in exchange for a second-base rental.

In each case, there was apprehension within the organization that Dombrowski was overpaying. That's tolerable when the farm system is loaded, but it's not sustainable, which is why the Red Sox suddenly find themselves in the market for a new GM.

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David Price's return to Red Sox rotation still uncertain, will pitch simulated game Tuesday

David Price's return to Red Sox rotation still uncertain, will pitch simulated game Tuesday

With their playoff hopes hanging by a thread (they began the night seven games back of the second AL wild-card spot), the Red Sox could use some good news on the starting pitching front after learning they'll be without Chris Sale the rest of the season.

They didn't get it Friday ahead of the series opener with the Padres in San Diego.

There had been speculation that David Price could be ready to start the series finale Sunday. That won't happen, manager Alex Cora told reporters before the game Friday.

Price, out since Aug. 4 with a cyst on his left wrist, had a bullpen session at Fenway Park on Thursday and will throw a simulated game in Colorado on Tuesday, "then we'll go from there," Cora said.

Eduardo Rodriguez starts Friday night, Nathan Eovaldi on Saturday and Sunday's starter is still to be determined. Lefty Brian Johnson (1-2, 6.58 ERA) had been filling Price's spot in the rotation.


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