If you remember five months ago, a large percentage of Red Sox fans were extremely frustrated with Chaim Bloom. After trading away players like Mookie Betts and Andrew Benintendi in prior years, to signing questionable names and a lot of filler options while he hopes the process of developing prospects starts to take shape. Let’s dive into “Old Friends & New: Red Sox Edition” and see where things stand as we approach halfway through the 2023 season.

Mookie Betts Trade

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At the end of the 2022 season, the Mookie Betts trade looked horrible. The star prospect return of the trade was Jeter Downs. Though he showed early potential, he seemed to peak as a AAA player and was eventually released this past offseason. In terms of major league contributors, OF Alex Verdugo had an average season and C Connor Wong had continued to struggle in the majors and spent most of his time in AAA.

Now as we enter the heart of the 2023 season, things are looking up a bit on this trade. Connor Wong has finally broken through and has developed into an average MLB-hitting catcher while being one of the best defensive backstops in the league. Alex Verdugo has also taken a step forward and has turned into an All-Star candidate in 2023. His bat has improved, showing more power and discipline at the plate. Defensively, he has improved dramatically from 2022 and has proved he can handle the dreaded right field at Fenway.

Betts in LA

In terms of Mookie Betts, he is slashing a .264 BA, and .365 OBP with 17 HRs and 43 RBIs. Overall at the plate, Betts is having a good season. That being said, it should be noted that he is also striking out at the highest rate of his career.

The biggest change in Betts’ play this year has been with his defense and speed. The perennial Gold Glover is off to a slower start defensively. According to Baseball Savant, his OAA is down from 2022, and his speed rating is down to below league average. The biggest worry with Betts has always been his size and how he will hold up into his mid 30’s. Though that is still a few years away, Betts is showing glimpses of those exact worries that many had. We’ll see how it plays out throughout the rest of this season and in years to come.

Andrew Benintendi Trade

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In 2021, the Red Sox decided to move on from Andrew Benintendi. They sent him to the Royals for OF Franchy Cordero, SP Josh Winckowski, and 3 PTBNL in a three-team deal. A few months ago, the trade looked bad and there was no denying that.

Benintendi went on to regain his groove as a contact hitter in Kansas City during the 2021 season. In 2022, he was eventually traded to the Yankees before signing a five-year, $75 million contract with the White Sox this past offseason. Cordero came to Boston as a fringe major leaguer. Though he showed flashes of real upside, he was never able to provide consistent quality at-bats. The Red Sox eventually moved on from Cordero.

Now in June 2023, the view of this trade looks to have flipped in the Red Sox’s favor. Josh Winckowski has settled into a role as a multi-inning reliever and has been a major weapon for Alex Cora in 2023. In 25 appearances, Winckowski has pitched 41.2 innings, with a 2.38 ERA with batters hitting .237 against him. Winckowski has improved dramatically from 2022, allowing fewer HR% and BB%, while boosting his SO%.

In 2023, Benintendi is batting .275 with a .345 OBP and one homerun. It’s reasonable to ask yourself the question of who you would rather have right now, and your answer should be Winckowski. He’s playing better and costs a fraction of what Benintendi does.

Rafael Devers Extension

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This past offseason was filled with ups and downs for the Red Sox. Fans were furious to see Xander Bogaerts walk out the door. It should be noted that the Padres gave him a ridiculous contract and it was smart not to match it. That being said, the failure from that whole situation comes from not extending him long-term before the 2022 season.

When fans watched Boegarts walk out the door, the attention immediately turned to Rafael Devers as he was due for a long-term deal as well. Fans were petrified by the idea of Chaim Bloom and the Red Sox front office allowing yet another home-grown star to leave. Fortunately for everyone, the Red Sox were able to lock Devers into a 10-year, $312.5 million contract. This deal locks Devers up through his age-36 season.

When everyone was projecting contracts for Devers, most everyone felt the bare minimum would be a 10-year, $300 million deal, with the chance those numbers could rise to 12+ years and north of 350 million. In the end, the completed extension looks to be a very reasonable deal for both sides and most importantly for the Red Sox, Devers will only be 36 by the end of it.

Trevor Story Signing

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After the lockout ended before the 2022 season, the Red Sox moved quickly and signed veteran shortstop Trevor Story to a six-year, $140 million contract. The expectation was that Story would move to second base as Xander Boegarts was the team’s shortstop, and Story’s history of arm issues would result in a better fit at 2B.

In his first season, Story batted .238 with 16 HRs and 66 RBIs over 94 games. On top of the multiple injuries that derailed his season, Story struggled to find consistency at the plate. Oddly enough, his power translated to Fenway and not his contact hitting so far.

In early January 2023, Story underwent an internal bracing procedure on his elbow that would force him out for at least half of the Red Sox 2023 season. The expectation is that this surgery should fix the nagging arm issues that Story has dealt with over the past few years, but the question is… should Chaim Bloom have expected this to come?

Masataka Yoshida Signing

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Among the five moves here, this one is the newest and still the biggest unknown yet. Nevertheless, here we are. When Masataka Yoshida was posted and available for teams to speak with, the expectations were that he’d take a bit to sign. That being said, the Red Sox didn’t give any other team a chance to beat them to signing Yoshida. Chaim Bloom worked quickly and offered Yoshida a five-year, $90 million contract. The deal was above the expectations for what he’d sign for. Yoshida and his agent Scott Boras ultimately decided to jump on the offer and Yoshida quickly become a Red Sox.

Once the signing was announced, ESPN Kiley McDaniel spoke with “anonymous executives” around the league asking what he is missing from the scouting reports to what the Red Sox paid for Yoshida.

“‘Nothing,’” replied one international scouting director. “‘Overpay for me … too rich imo,’” from another scouting director. A third exec: “‘I have no idea.’” A fourth: “‘Nothing … I wish they and him luck.’” A fifth: “‘We thought he was worth less than half of what they paid.’” A sixth added, “‘I have no words.’”

Now as Yoshida approaches 200 career MLB at-bats, it has become very clear. Either those executives failed to properly evaluate Yoshida, or they were bitter that the Red Sox beat them to Yoshida.

In 48 games, Yoshida is batting .308 (seventh in MLB) with a .381 OBP (16th), seven home runs, and 37 RBIs. Everything that the Red Sox said they saw in him seems to be translating to the MLB. His SO% ranks fifth best in the MLB and has been one of the best hitters in baseball this year. It’s still early into Yoshida’s MLB career, but if this is the Yoshida we will see for the next five seasons, this will end up being one of the best moves of Chaim Bloom’s career.

See the Light

Whether you find yourself as part of the “anti-Bloom” agenda, part of the “Bloomanati” or somewhere in between, that’s up to you. One thing is clear though, things look a bit better than they did five months ago. Both the Betts and Benintendi trades look much better (though the Betts trade still isn’t a win). The Devers extension is what everyone hoped for and the cost was reasonable. Finally, the Yoshida signing looks to be a major win for Chaim Bloom so far.

There is still plenty of season left in 2023 and a lot can change, but the tides have shifted a bit. We’re seeing a bit of what Bloom is pushing for and his prospects in the pipeline are performing well. If he can stick around long enough for them to find their way to the major league, we might just see him prove everyone wrong. His “3-5 year vision” is currently in year four. Let’s hope he continues to build the Red Sox in the right direction.

For more sports content, visit Belly Up Sports and follow me on Twitter, @MattCouture5.

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Matt Couture

Massachusetts native and life long Boston sports fan

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