Ranking the Red Sox 5 best moves under Chaim Bloom

BOSTON, MA - SEPTEMBER 22: Chief Baseball Officer Chaim Bloom of the Boston Red Sox looks on during a pre-game ceremony in recognition of the Minor League Awards before a game against the New York Mets on September 22, 2021 at Fenway Park in Boston, Massachusetts. (Photo by Billie Weiss/Boston Red Sox/Getty Images)
BOSTON, MA - SEPTEMBER 22: Chief Baseball Officer Chaim Bloom of the Boston Red Sox looks on during a pre-game ceremony in recognition of the Minor League Awards before a game against the New York Mets on September 22, 2021 at Fenway Park in Boston, Massachusetts. (Photo by Billie Weiss/Boston Red Sox/Getty Images)
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CLEVELAND, OHIO – JUNE 24: Starting pitcher Nick Pivetta #37 of the Boston Red Sox reacts after giving up a homer during the fourth inning against the Cleveland Guardians at Progressive Field on June 24, 2022 in Cleveland, Ohio. (Photo by Jason Miller/Getty Images)
CLEVELAND, OHIO – JUNE 24: Starting pitcher Nick Pivetta #37 of the Boston Red Sox reacts after giving up a homer during the fourth inning against the Cleveland Guardians at Progressive Field on June 24, 2022 in Cleveland, Ohio. (Photo by Jason Miller/Getty Images) /

Ranking Chaim Bloom’s best moves with the Red Sox

There was a time not too long ago when Chaim Bloom was getting a lot of heat from Boston Red Sox fans. The club was sitting at 10-19 with a punchless offense and a hapless bullpen, and every move the team’s Chief Baseball Officer made the previous offseason was being second guessed. Why did they trade 30 home run man Hunter Renfroe for Jackie Bradley Jr.? Why didn’t they re-sign Kyle Schwarber? Why didn’t they sign a premier closer?

Now that the Red Sox have turned it around, I think it’s time to give Bloom his due. During his two-plus years with the Red Sox, his great moves have far exceeded his poor ones, and he’s had some absolute gems along the way.

Here are Bloom’s five best moves as CBO of the Red Sox.

BOSTON, MA – MAY 29: Enrique Hernández #5 of the Boston Red Sox rides in a laundry cart through the dugout after hitting a home run during the fourth inning of a game against the Baltimore Orioles on May 29, 2022 at Fenway Park in Boston, Massachusetts. (Photo by Maddie Malhotra/Boston Red Sox/Getty Images
BOSTON, MA – MAY 29: Enrique Hernández #5 of the Boston Red Sox rides in a laundry cart through the dugout after hitting a home run during the fourth inning of a game against the Baltimore Orioles on May 29, 2022 at Fenway Park in Boston, Massachusetts. (Photo by Maddie Malhotra/Boston Red Sox/Getty Images /

Red Sox sign Kiké Hernández to a 2-year, $14 million deal

There was not much fanfare from Red Sox Nation when Chaim Bloom brought Kiké Hernández aboard two winters ago. Sure, Hernández had been a useful player for some really good Dodgers teams, but he was looked at more of a utility piece than an everyday player. In his six years in Los Angeles, he topped the .250 average and 20 home run mark just one time each.

With such a meager resume entering 2021, it was a surprise to many when Alex Cora installed Hernández as the everyday centerfielder and leadoff hitter. Yet Hernández responded with a career-best season, setting personal highs in at-bats, runs, on-base-percentage, and WAR. He also proved to be one of the best defensive outfielders in the game and went nuclear in the postseason with a .408/.423/.837 slash line and five home runs.

If Hernández was able to continue his 2021 success, he would be much higher on this list. Yet this season has been a massive struggle, first with an offensive slump and then with a hip flexor strain that landed him on the IL. Still, Hernández’s value has far exceeded expectations, especially considering he’s only making $7 million a year.

BOSTON, MASSACHUSETTS – OCTOBER 18: Kyle Schwarber #18 of the Boston Red Sox rounds the bases after his home run as Yuli Gurriel #10 of the Houston Astros looks on during Game Three of the American League Championship Series at Fenway Park on October 18, 2021 in Boston, Massachusetts. (Photo by Elsa/Getty Images)
BOSTON, MASSACHUSETTS – OCTOBER 18: Kyle Schwarber #18 of the Boston Red Sox rounds the bases after his home run as Yuli Gurriel #10 of the Houston Astros looks on during Game Three of the American League Championship Series at Fenway Park on October 18, 2021 in Boston, Massachusetts. (Photo by Elsa/Getty Images) /

Red Sox trade Aldo Ramirez for Kyle Schwarber

The 2021 trade deadline was just around the corner, and it was clear the Red Sox needed to do something. The AL East race was beginning to tighten up, and their rivals had already made critical moves to upgrade their offense. The Yankees had traded for sluggers Anthony Rizzo and Joey Gallo, while the Rays got one of the best designated hitters in the game in Nelson Cruz.

There were many bats on the market for the Red Sox to choose from, including former MVP Kris Bryant and All-Stars Javier Baez, Trea Turner and Starling Marte. Yet the man the Red Sox went after was a .230 hitter entering 2021 and nursing a serious hamstring injury at the time of the acquisition. Nobody could have expected just how much of an impact Kyle Schwarber would make.

Schwarber joined the Red Sox in mid-August, and transformed the Red Sox lineup with his power and patience. He slashed a phenomenal .291/.435/.522, working 33 walks in just 41 games. The slugger also played a major part in the Red Sox playoff run, homering three times including a grand slam before getting overmatched by the Astros in the ALCS.

The value the Red Sox got from this deal was enormous, especially considering how little they gave up to gave him. The only prospect they gave up in the deal was Aldo Ramirez, who had a 8.33 ERA after the deal and has yet to appear in a game this season.

If Schwarber was re-signed this past offseason, this deal would be an all-timer. But considering he departed for Philadelphia and the Red Sox got just half a season of Schwarber that didn’t end in a championship, this moves come in at just number four.

OAKLAND, CA – JUNE 5: Franchy Cordero #16 of the Boston Red Sox bats during the game against the Oakland Athletics at RingCentral Coliseum on June 5, 2022 in Oakland, California. The Red Sox defeated the Athletics 5-2. (Photo by Michael Zagaris/Oakland Athletics/Getty Images)
OAKLAND, CA – JUNE 5: Franchy Cordero #16 of the Boston Red Sox bats during the game against the Oakland Athletics at RingCentral Coliseum on June 5, 2022 in Oakland, California. The Red Sox defeated the Athletics 5-2. (Photo by Michael Zagaris/Oakland Athletics/Getty Images) /

Red Sox trade Andrew Benintendi

At first glance, this trade may not seem like a massive win for the Red Sox. Andrew Benintendi has won a Gold Glove for the Royals and is currently hitting .299. Franchy Cordero, meanwhile, has hit just .202 over two years for the Red Sox.

The surface-level stats, however, don’t tell the whole story. Benintendi may have a high batting average, but he’s homered just three times and has an unimpressive .757 OPS. He’s also a free agent at the end of the season, and considering he’s just 27, is likely to command a nine-figure contract that is well beyond his value.

While Cordero doesn’t have the raw average of Benintendi, he’s shown great improvement during his second year in Boston. He’s cut his strikeout rate by 10% and upped his walk rate from 5.9% to 9.9%, and he hits the ball as hard as anyone in the majors.

Then there are the prospects. Three of the four haven’t made much progress, but the fourth looks to be a big hit. Josh Winckowski advanced to Triple-A Pawtucket in his first season in the Red Sox organization and took another step forward this year, posting a 3.38 ERA and a terrific 5.38 K/BB ratio. His performance earned him a promotion to the show, and he’s made the most of it with 3-1 record and a 3.60 ERA over his first four starts.

As unpopular as the Benintendi trade was at the time, it looks now to be the right long-term move. If Cordero’s baseline numbers start matching up with his underlying metrics and Winckowski becomes a regular member of the rotation, this deal will move even more in the Red Sox column.

BOSTON, MASSACHUSETTS – JUNE 01: Starting pitcher Garrett Whitlock #72 of the Boston Red Sox throws against the Cincinnati Reds during the first inning at Fenway Park on June 01, 2022 in Boston, Massachusetts. (Photo by Maddie Meyer/Getty Images)
BOSTON, MASSACHUSETTS – JUNE 01: Starting pitcher Garrett Whitlock #72 of the Boston Red Sox throws against the Cincinnati Reds during the first inning at Fenway Park on June 01, 2022 in Boston, Massachusetts. (Photo by Maddie Meyer/Getty Images) /

Red Sox select Garrett Whitlock in the Rule 5 draft

The Rule 5 Draft is overlooked by many major league fans, and it makes sense why. Players are only eligible for the draft if their team chooses not to protect them on the 40-man roster, meaning that the players up for grabs are not the biggest name prospects. The Red Sox, for example, only had kept one player from the Rule 5 draft during the 2010s:  Jonathan Arauz, who was just released this past week after posting a .600 OPS in 147 at bats for the club.

In most years, the Red Sox and most other contenders choose to sit out the Rule 5 draft, considering the players they choose have to stay on the big league roster for the entire year. In 2020 however, there was a player they simply could not pass on. After coming to the Yankees as an 18th rounder in the 2017, Garrett Whitlock broke out in 2018, posting a 1.86 ERA and advancing all the way to Double-A.

Yet after a midseason 2019 Tommy John surgery, the Yankees decided they weren’t going to wait around, and left him unprotected for the 2020 Rule 5 draft. Their archrivals pounced, and made Whitlock a critical piece of their bullpen. He was so dominant that he ended up being Alex Cora’s most trusted reliever in the postseason.

His 2022 campaign has not been nearly as strong, as he’s struggled to adjust to a move to the rotation, and he’s currently on the IL with a hip injury. Yet even if Whitlock never is quite as dominant as he was in 2021, his contributions to the Red Sox should far exceed what is expected of a Rule 5 pick.

BOSTON, MA – MAY 29: Pitcher Nick Pivetta #37 of the Boston Red Sox pumps his fist after a double play ended the fourth inning against the Baltimore Orioles at Fenway Park on May 29, 2022 in Boston, Massachusetts. (Photo By Winslow Townson/Getty Images)
BOSTON, MA – MAY 29: Pitcher Nick Pivetta #37 of the Boston Red Sox pumps his fist after a double play ended the fourth inning against the Baltimore Orioles at Fenway Park on May 29, 2022 in Boston, Massachusetts. (Photo By Winslow Townson/Getty Images) /

Red Sox trade for Nick Pivetta and Connor Seabold

It doesn’t get much better than this. It was clear from the start than the 2020 Red Sox weren’t going anywhere, and as the trade deadline approached, the Red Sox were looking to offload some pieces. The only true piece of value Bloom had to work with was Brandon Workman, a closer coming off a breaking 2019 season.

Bloom found a suitor in the pitching-needy Philadelphia Phillies, who agreed to take on both Brandon Workman and fellow reliever Heath Hembree. It’s safe to say that neither played panned out. Hembree had a 12.54 ERA before being optioned at the end of the season, while Workman blew three of his eight save opportunities and actually ended up back with the Red Sox in 2021.

Usually when a team sells at the trade deadline, they are looking for prospects in return. And while the Red Sox did acquire one prospect in return (Connor Seabold, who dominated Triple-A en route to a major league callup), the centerpiece of the deal already had 71 major league starts under his belt at the time of his acquisition.

Nick Pivetta always had the stuff of a frontline starter, but wildness and overall inconsistency plagued him during his time in Philly. His 2021 regular season wasn’t really anything special, as evident by his 4.53 ERA, but he became a fan favorite in the postseason by dominating the Rays in extra innings in the critical Game 3 and tossing five innings of one run ball in the ALCS against the Astros.

This season, however, has transitioned this deal from a clear Red Sox win to a straight up train robbery. After a rocky start, Pivetta has been one of the game’s best pitchers since early May, posting a 8-1 record and a 1.85 ERA over his last ten starts.

For the Red Sox to get a frontline starting pitcher and a top prospect in the same deal is one thing, but to get them for two relievers who have produced nothing since the trade is an all-time move. This is Chaim Bloom’s best work.

Jarren Duran has earned his starting spot. dark. Next

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