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Prospect promotions, payroll concerns, Chaim Blooms tenure, more: Red Sox mailbag

The Red Sox are off Thursday, for the first time in 19 days, and then return home for a tough seven-game stretch against Cleveland and Toronto beginning Friday.

We figured it was a good time to take some reader questions for a mailbag.

On Wednesday, we posted part one of the mailbag with questions about the rotation construction, how injuries are affecting this team, contract extension talks and the future of some depth players.

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In part two here, we’ll answer some prospect questions, look at how long a leash chief baseball officer Chaim Bloom has, and what the future of the team looks like, among other topics. (Note: Questions have been lightly edited for style and clarity.)

Am I correct in my contention that the payroll/roster construction problem isn’t that this ownership won’t spend, but rather that they have rarely spent wisely/effectively, while still usually building high-ish to high payroll rosters? They spend good money to build bad teams. — David J. via The Athletic app

I understand the sentiment and there’s definitely some truth to it. At the same time, they proved they’re willing to spend when they want to with Rafael Devers’ $313 million deal. There are plenty of contracts you could debate have been misses. Chris Sale’s contract is up for debate; Trevor Story has been injured more than he’s played so far on his six-year deal; Jake Diekman’s two-year, $8 million deal last year obviously didn’t work out; neither did Garrett Richards’ deal; and while Matt Barnes looked excellent when he signed a two-year, $18.75 million deal in 2021, it all went south shortly thereafter. The list goes on.

Still, there have been some decent signings: Michael Wacha last year at one year, $7 million; Adam Duvall this year at one year, $7 million; Kenley Jansen for two years, $32 million; even Kiké Hernandez to a one-year, $10 million contract last summer when he probably would have gotten more on the open market this winter. But those are all relatively small splashes. I think there have been some effective decisions, and also some awful ones. The Devers’ deal legacy remains to be seen, but he deserved to be paid up front. So I’ll give it to you that the two biggest contracts thus far in Sale and Story haven’t produced the needed results.

Do the Sox remain committed to building teams that don’t obliterate the salary cap? We’ve heard statements like that, owners saying they’re committed to keeping payroll down. I get it as a business decision. But it’s led to some pretty lackluster teams. — Les G. via The Athletic app

While there is no hard salary cap, the Red Sox have hovered around or just above the luxury tax threshold the last few years, which this year is $233 million. They paid the luxury tax penalty last season for going over the threshold and that’s when they had an opportunity at the deadline to go under, so it’s not as if they are morally opposed to paying the penalty.  This year, the Red Sox’s current payroll is roughly $225 million. (Chad Jennings had a good Red Sox payroll breakdown earlier this year.) The ownership group has said on a few occasions they’re not going to spend upward of $300 million like the Mets and Steven Cohen, but seven teams, as of now, are set to go over that $233 million mark (Mets, Yankees, Padres, Phillies, Jays, Dodgers, Braves). So it’s fair to argue whether the Red Sox are spending wisely, as noted above, and they certainly aren’t among the top few teams in the league spending-wise as they have been in the past.

Trevor Story in September 2022. (James A. Pittman / USA Today)

Is there any chance the Red Sox end the regular season having been anything better than mediocre-at-best in an overall sense? — David J. via The Athletic app

There’s always a chance. Sure, you can look at their overall current record, hovering around .500, and think that’s what they’ll be all year. But at the same time, they’ve endured some significant injuries over the first month and have still managed a .500 record while playing some good teams. The American League East is undoubtedly tough, but if the Red Sox played in almost any other division, they’d be in second or third place. They just finished a 19-day stretch of playing games every day, their longest such stretch of the season, and went 10-9. So I think there’s a chance they could be better than mediocre, especially once they get healthier with the return of Story and Duvall by July. The biggest key will be getting more out of their rotation.

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If the season ends without a playoff appearance, do you see the Sox management making a big splurge on say Shohei Ohtani or another big free agent? It’s a great free-agent class. — Samuel C. via The Athletic app

The Red Sox heavily pursued Ohtani in 2017 (The Boston Globe’s Alex Speier had a great story on this in 2018.) The Red Sox obviously have taken a conservative approach with free agents in recent years. Story’s six-year, $120 million is the most they’ve spent under Bloom on a free agent with Masataka Yoshida’s five-year, $90 million coming in second. Ohtani would be the type of player to pursue given his generational talent as well as his international appeal and it’s possible the Red Sox have been reshuffling their finances in an effort to make an all-out pursuit of Ohtani this winter. But given the way they’ve operated of late, I have a hard time seeing them outbidding teams like the Mets, Dodgers, Yankees or Padres. It’ll be the biggest storyline of the offseason, regardless.

Can we expect the front office to be cleaned out if the Red Sox are still a .500 team at the All-Star break? — @GrayHairJoe via Twitter

By the All-Star break, I’d say no. By the end of the season … see the next question.

Will Chaim Bloom be replaced during the season if the team performs to current expectations (bottom of the division)? What is the history of the Fenway group with mid-season management replacements? — Scott C. via The Athletic app

Theo Epstein left on his own following the 2011 season, but the earliest this ownership group has fired or replaced a GM-type was late in the second half, which they’ve done twice. They demoted Ben Cherington and replaced him with Dave Dombrowski in mid-August 2015 and then they fired Dombrowski the first week of September 2019, but didn’t bring in Bloom until late October. Both Cherington and Dombrowski held the job for four years and each won a World Series. Bloom is in his fourth year of a five-year deal, though that doesn’t necessarily mean the job is guaranteed for five years. Right now the team is getting by and doing better than expected in many areas, but another last-place finish would be a tough look. By midseason, if things go off the rails, or if there’s a chance for deadline moves and they’re flubbed, I think Bloom’s job security will be a big topic.

In the dark hours of the night, do Sox ownership or management have any regrets about not finding a way to pay and keep Mookie Betts? Hearing of his playing shortstop for the Dodgers (albeit in an emergency) seemed the final troll on what shoulda, coulda, woulda been. — Andrew S. via The Athletic app

The dominoes of these massive contracts are so interesting to examine. Would the Red Sox even have offered Xander Bogaerts or Chris Sale the 2019 extensions if they were convinced they were going to work out a Betts deal that upcoming offseason? Meanwhile, the Betts shortstop news made me think back to this 2015 story I wrote on how the Red Sox discovered Betts. Danny Watkins, the scout who signed him, first noticed Betts, then a senior in high school, making a slick behind-the-back move while playing shortstop.

As far as the trade, CEO Sam Kennedy talked about regretting how they publicly handled it all. I think the biggest regret overall might be that they didn’t work something out far sooner with Betts even before the eight-year, $200 million offer in 2017. They’ve always said they weren’t going to go past a certain number, but if they’d started sooner, things might be different. We’ll never know. Bloom has discussed wanting to sign younger players to extensions earlier in their careers as he did with Garrett Whitlock. Whitlock’s was a modest four-year deal, but one that was signed after his first season in the majors. That could be a blueprint for future extensions.

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​​What does this team look like in five years? More than half the current roster will be retired by then and the replacements look shaky at best, particularly on the pitching side. We have one really good prospect and a bunch of maybes. — Ben H. via The Athletic app

This current team is a mix of veterans and young players. So yes, Chris Sale, Kenley Jansen, Justin Turner and Corey Kluber likely won’t be around, but Tanner Houck, Garrett Whitlock, Brayan Bello, Kutter Crawford and Josh Winckowski all should be. I don’t think that’s necessarily a shaky group. On the position player side Rafael Devers, Trevor Story, Triston Casas, Jarren Duran, and Connor Wong would all still be under contract. And as far as prospects, Marcelo Mayer, Ceddanne Rafaeala, Miguel Bleis, Blaze Jordan, Nick Yorke, Bryan Mata, Shane Drohan and perhaps promising Single-A pitching prospect Luis Perales could all be in the mix among many others. There will be trades and some players won’t pan out, but there are more players here than it seems, which is part of what Bloom has been trying to do with his sustainable roster approach.

How does the current farm system compare to past administrations at the same point in their tenure? Bloom was brought in to make a sustainable organization and so far the results are lacking. — Anonymous U. via The Athletic app

I’d say the immediate results are lacking, for sure. The team the last couple of seasons has been inconsistent and frustrating to watch. But the sustainable approach requires a much more long-term view. If you refer to the previous question, there are pieces here, but it’s going to take time. People don’t necessarily want to wait that long, which is understandable, but I don’t think that means it’s not working. Tanner Houck was drafted in 2017 and it’s only now, six years later, that we’re starting to see some more consistent results. As far as the past, the comparisons aren’t apples to apples, but since you asked, we’ll look at Baseball America’s organizational rankings. BA currently has the Red Sox farm system as 10th in baseball. In Dombrowski’s final season, four years into the job, the Red Sox were 30th after having graduated several prospects. In 2015, in Cherington’s fourth and final year, the team ranked second.

Who do you think is likely to be the next prospect called up? — Mick L. via The Athletic app

It probably makes most sense to look at the minor leaguers on the 40-man roster, since they have the most direct path to the majors. Of that group, six players have yet to make their big league debuts: infielder David Hamilton, outfielder Wilyer Abreu, infielder/outfielder Ceddanne Rafaela and pitchers Bryan Mata, Chris Murphy and Brandon Walter. None of the pitchers have been off to particularly strong starts so I think each of them will continue to get innings in Triple-A Worcester.

Rafaela spent a good portion of spring training with the big league team, but started the year off in Double A as the Red Sox want him to continue refining his approach at the plate and with his swing decisions. He could be a midseason call-up, though. Abreu was acquired alongside Enmanuel Valdez for Christian Vazquez last summer. Valdez was called up recently to help with the infield depth, but Abreu will probably stick in Worcester for a while unless there’s an emergency in the outfield.

That leaves us with Hamilton, who’s been off to a hot start in Worcester, hitting .319 with a .950 OPS with three doubles, a triple and four homers through 18 games. He’s the fastest prospect in the system and his 70 steals last season in Portland tied a Red Sox franchise record with Jacoby Ellsbury, who had 70 steals in the majors in 2009. Hamilton already has 11 steals so far this year. Director of player development Brian Abraham told Chad Jennings they really want to solidify some of the changes Hamilton made with his bat speed and bat path this winter so he’ll be in Worcester for a while longer. But he’s a good defender and has elite speed and with Yu Chang out and needing hamate bone surgery, I think Hamilton might force their hand soon and he could be up within the next few weeks.

If you’re asking about which big-name, top-five prospect will be debuting next, Nick Yorke is in Double A and the swing changes he made in the offseason seem to be taking hold. He could be in Triple A by the end of the season. It’s unlikely, but there’s a slight chance they call him up at the very end of the year, though I imagine 2024 is more likely when you’ll see him. Marcelo Mayer is a level beneath him in High A and is also expected to debut in 2024.

(Top photo: Tommy Gilligan / USA Today)

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Artie Phelan

Update: 2024-04-23