Tomase: Assessing Chaim Bloom's biggest wins, losses with Red Sox


Chaim Bloom joined the Red Sox in 2019 on Halloween and the ensuing two years have provided a clear picture of how the chief baseball officer likes to operate, but with one big question unanswered.

Blending a little of Theo Epstein's "why not us?" audaciousness with a lot of Ben Cherington's pragmatism, Bloom has very quickly succeeded in making the Red Sox a short-term contender while building towards his ultimate goal of creating an organization capable of sustaining long-term success.

Counting players allowed to leave in free agency and lost on waivers, Bloom has made 171 transactions (per Baseball-Reference) since assuming the helm, and the patterns illustrate just how uninterested he is in short-term solutions that come at the expense of his long-term vision.

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With the exception of trading well-regarded minor league right-hander Aldo Ramirez to the Nationals for rental Kyle Schwarber, a case can be made that Bloom's other 170 moves have prioritized the future. He has consistently maintained flexibility by signing players to one- and two-year contracts, with upside signings including team options that give Bloom the chance to decide if he wants a player long-term. In the case of Garrett Richards, the answer was no. Perhaps rehabbing left-hander James Paxton will be a yes.

If there's a question that we're still trying to ascertain, it's when Bloom will spend his considerable resources for real. Thus far, the biggest contract he has bestowed is the two years and $14 million he gave Kiké Hernández to successfully prove he's an everyday player and not a super-utilityman.


With tantalizing high-end free agents like Trevor Story and Carlos Correa still unsigned, the Red Sox will be linked to them just because. But we still don't know if, when, or how Bloom will make that leap. If ownership felt any inclination to grow impatient and nudge him in that direction, as has been its wont in the past, Bloom bought himself time with a rousing 2021 that ended two games shy of an improbable World Series despite a series of mostly anonymous pickups.

Don't be surprised if Bloom gives us more of the same -- acquisitions that elicit little more than a shrug during the winter before paying dividends during the summer.

John Tomase

More likely, of course, is that Bloom is following ownership's mandate to a tee. He arrived just in time to find a new home for franchise cornerstone Mookie Betts, a deal that ultimately saved the Red Sox a lot of money without necessarily supplying much top-end talent.

Regardless, as baptisms go, that one felt particularly fiery, and Bloom never wavered. He held out until spring training before sending Betts to the Dodgers and then delayed the completion of the three-way trade when he didn't like the look of Brusdar Graterol's medicals.

Instead of letting that trade define him, Bloom set about rebuilding the organization from the ground up. His bargain additions last winter yielded a playoff team, and his first two drafts already look like winners, with 2020 first-rounder Nick Yorke far exceeding industry expectations and this year's fourth overall pick, Marcelo Mayer, widely considered the most talented player in the 2021 MLB Draft.

Bloom has yet to flex his financial muscles except in one very specific way, which is to buy the final year of an overpriced free agent as a means of acquiring prospects. He did so with the Yankees last year, acquiring the roughly $9 million owed Adam Ottavino to add right-hander Frank German, who failed to deliver at Double-A. He did so again last week when he reacquired Jackie Bradley, Jr. from the Brewers for outfielder Hunter Renfroe and a pair of infield prospects who slot into the middle of Boston's suddenly deeper farm system.

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This weird pre-lockout phase of the offseason saw Bloom remain mostly sidelined, content to pick through what's left when the signing period resumes following the ratification of the next CBA. While teams like the Rangers committed half a billion dollars to their middle infield and the Tigers struck big deals with Javier Baez and Eduardo Rodriguez, Bloom stayed disciplined. He acquired Paxton in a move that's more about 2023 and 2024 than next year, signed old friend Rich Hill to spin his ageless curveballs in the rotation, and traded Renfroe in a move that opens up a corner outfield spot for either free agency (Schwarber?) or the trade market.

While there's always a chance the Red Sox make a splash for someone like Story, an All-Star shortstop with tremendous power, don't be surprised if Bloom gives us more of the same -- acquisitions that elicit little more than a shrug during the winter before paying dividends during the summer.


He has earned some benefit of the doubt, because two years into the job, it certainly appears the Red Sox are in capable hands.

So what are Chaim Bloom's best and worst moves since joining the Red Sox? Let's break down the top five of each.

Best moves


1. Taking Garrett Whitlock in Rule 5 draft

This would be a home run in any scenario, but the fact that Bloom stole one of the most promising young relievers in the game from the rival Yankees makes it all the sweeter. This was by no means an obvious pick. Whitlock hadn't pitched competitively since 2019 while recovering from Tommy John and the Red Sox committed to keeping him on the roster for the entire 2021 season anyway.

He delivered and then some, posting a 1.96 ERA and establishing his floor as primary setup man, with a ceiling of legitimate top-three starter.

2. Brandon Workman trade

Red Sox players and coaches held immense respect for Workman, who contributed to World Series titles in 2013 and 2018, but his stuff had regressed noticeably when Bloom shipped him to the desperate Phillies at the 2020 trade deadline for underachieving right-hander Nick Pivetta and prospect Connor Seabold.

Workman made a bad bullpen situation in Philly even worse, and Pivetta spent a month at the alternate site before winning two starts in September. The fiery Canadian made 30 starts last season and then posted a 2.63 ERA in the playoffs as one of Boston's best starters.

Not even 29, he should have a home in the Red Sox rotation moving forward.

3. Signing Kiké Hernández

During an offseason that saw Bloom emphasize versatility, no player better embodied that concept than Hernández. The Red Sox raised eyebrows by claiming they believed he could be an everyday player, but the athletic super-utilityman proved them right by starting at second, quickly shifting to center, and immediately proving indispensable.

He delivered Gold Glove-caliber defense in place of Jackie Bradley Jr., he found discipline atop the lineup, and he proved the value of postseason experience by hitting .408 and slamming five homers in 11 games as the Red Sox fell two wins shy of the World Series. Not bad for two years and $14 million.

4. Landing Kyle Schwarber at trade deadline

We don't spill ink anymore, but it's worth considering how any bits and bytes were loosed into cyberspace criticizing this move for the first two weeks of August when Schwarber couldn't play and the Red Sox were in freefall.

Bloom maintained that he believed the left-handed slugger to be the most impactful bat moved at the deadline, and he was ultimately proven right. Once he recovered from a hamstring strain, Schwarber teed off, hitting .291 with seven homers and a .957 OPS in 41 games.

He transformed an overly right-handed Red Sox lineup by providing a commanding presence from the left side, quickly becoming a fan favorite in the process.


5. Finding Christian Arroyo

There are plenty of other options here, whether it was effectively exchanging backup catcher Sandy Leon for the more productive Kevin Plawecki, or identifying Hunter Renfroe as a worthy target last winter, or grabbing Jose Iglesias to plug a hole in September. But Bloom's acquisition of Arroyo off waivers in August of 2020 illustrated his approach to scouring every surface for talent.

A former first-round pick turned bust with the Giants and Indians, Arroyo found a home with the Red Sox by making himself versatile. He played second base and shortstop, basically tore his groin trying to learn first base in a pinch, and even delivered an inning of relief. He may never be a star, but he could've easily fallen through the cracks, and Bloom didn't let that happen.

Worst moves


1. Signing Garrett Richards

With two-time Cy Young Award winner Corey Kluber also available, the Red Sox went in a different direction, signing the right-handed Richards despite a history of being injured and not delivering results commensurate with his talent.

His 2021 season ended up being a rollercoaster, from a bad start marked by wayward mechanics, to a strong rebound, to crumbling helplessly when MLB cracked down on the use of foreign substances, to a belated run of usefulness out of the bullpen, to a season-ending injury in the playoffs.

The Red Sox signed Richards to a one-year deal with an option that gave them some control if they liked what they saw. They instead pulled the plug on an experiment that yielded a 4.87 ERA and too much whining and complaining.

2. Andrew Benintendi trade

If there's one aspect of the Rays Way we often get wrong, it's the idea that Tampa Bay wins every trade. During Bloom's time in the Trop, Tampa jettisoned a parade of former standouts without always receiving a winning return.

Benintendi is in danger of joining the likes of Evan Longoria and Jake Odorizzi on this list. He won a Gold Glove in his debut with the Royals and would've been more useful to the 2021 Red Sox than replacement Franchy Cordero. The Red Sox received four other prospects in the deal, but for the time being, the only one with a realistic chance of impacting the big leagues is right-hander Josh Winckowski.

3. Mookie Betts trade

Plenty of you would undoubtedly put this No. 1, and I've previously argued it could make the best-of list. Recognizing that Bloom's hands were tied by a desire to drop below the luxury tax threshold, there weren't a lot of clubs that could afford Betts as well as half of the $96 million remaining on David Price's contract.

The Dodgers were pretty much it, and it looks like the Red Sox traded an MVP for a slightly above-average outfielder in Alex Verdugo as well as two middling prospects (Jeter Downs, Connor Wong).


It's sad to say, but whatever value the Red Sox derived from the trade likely traces to dumping Price's salary, which the Red Sox didn't exactly pump back into the product. It may have been necessary, but it's hard to call that a win.

4. Signing Marwin Gonzalez

The flip side of the Hernández signing is Gonzalez. He arrived with a similarly impeccable pedigree, and manager Alex Cora excitedly empowered him to lead in the locker room, but Gonzalez's bat simply didn't cooperate.

The switch hitter batted just .202 before being released in August, his ability to catch up to fastballs perhaps permanently compromised. He joined the Astros and fared no better, batting .176 but at least reaching another World Series after Houston eliminated the Red Sox.

5. Signing Jose Peraza

For the longest time in the winter of 2020, Peraza served as the extent of Bloom's efforts. He signed in December as a low-cost flyer who'd had one half decent season with the Reds in 2018, batting .288 with 14 homers.

Given the chance to claim the second base job with Dustin Pedroia's career effectively over, Perez responded by going 4 for 5 on Opening Day before entering an immediate tailspin. He ended up hitting .225 and the Red Sox let him walk the following winter.