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Chaim Bloom’s Top 10 moves part 2 #5-1

After two years in Boston, Chaim Bloom has made some outstanding moves. Now is time to break down the top 5.

Image: @RedSox/Twitter

A few weeks ago, I began the process of ranking the top moves of Chaim Bloom’s tenure in Boston. Last time, we broke down those that landed in the back half of my top 10, including the acquisitions of 2021 breakouts Enrique Hernández and Hunter Renfroe. That list can be found here. Today, we take a look at the true standouts of the bunch, the top 5. (Please note: Except where otherwise specified, all prospect rankings are from Sox Prospects, the most trusted authority on Red Sox prospects)

5. 2021 Amateur Draft

Calling an entire draft a single “move” is, admittedly, cheating to some degree. Nevertheless, Chaim Bloom has already flexed his muscles in the draft in such a way that demands placement on this list. If there was anything positive to come out of the 2020 season, it was the fourth overall pick in the subsequent draft, the highest the team had selected in over 50 years. Speculation swirled about what direction would be taken with this pick. Many were hopeful that Vanderbilt righty Jack Leiter would fall to fourth. Others were excited at the prospect of Leiter’s teammate, Kumar Rocker, coming to Boston. Neither happened, as Leiter went 2nd overall to the Rangers, while Rocker fell to the Mets at 10th. Instead, Chaim Bloom took high school shortstop Marcelo Mayer. While there was not a clear-cut #1 overall pick akin to Bryce Harper or Stephen Strasburg available in this year’s draft, most rankings did have Mayer pegged as the #1 player in the class. When Bloom and company had arguably the most talented player in the draft class fall into their laps at four, it was a no-brainer. Mayer instantly became a top prospect. While Sox Prospects has him ranked 2nd, behind only Triston Casas, MLB Pipeline ranks him as the organization’s top prospect and the ninth-best prospect in baseball.

The draft does, however, extend beyond the first round, and Bloom continued to add value throughout the draft. In the third round, the team drafted Tyler McDonough (ranked 21st) out of NC State. McDonough is a utility player who projects as a second baseman but has experience in the outfield, infield, and behind the dish. He has a strong approach at the plate which allows him to draw walks while limiting strikeouts. He lacks a true stand-out skill, but projects as average in most areas, which should allow him to make an impact at the Major League level, especially with his versatility. In the 5th round, Nathan Hickey (ranked 29th), a catcher from the University of Florida, was selected. It’s unclear if Hickey will be able to stick behind the plate long term, but his bat is expected to be valuable enough that he could move to a less demanding position and still be a valuable player. If he can make it work as a catcher, then his bat becomes that much more valuable. The last player I’d like to highlight from this draft class is Niko Kavadas (ranked 44th), a first baseman from Notre Dame. Kavadas is antithetical to McDonough in just about every way. Kavadas has one true calling card, his prolific power. He homered more frequently than anybody else in NCAA Division I in 2021, hitting 0.47 home runs per game. If Kavadas ever loses his power stroke, it’d be the end of his status as a prospect, as power is his only above-average tool.

4. Acquiring Kyle Schwarber for Aldo Ramirez

Kyle Schwarber and the Red Sox go together like Barry Bonds and intentional walks. The fit wasn’t so obvious at first, as the Red Sox seemed to be in the market for a first baseman, a position Schwarber had virtually no experience at as a professional. Luckily, Chaim Bloom is smart enough to know that if the bat is good enough, you can figure out where to put the glove later. Schwarber changed the entire dynamic of the lineup once he joined it. All season the team had struggled to command the strike zone, frequently taking themselves out of at-bats by swinging at waste pitches. Schwarber, as evident by his .435 OBP with Boston, worked against that. After his debut, the entire team began to show a more refined approach at the plate, most notably Bobby Dalbec. Despite being acquired to replace Dalbec, Schwarber worked with him in the cage, leading to Dalbec being a premier hitter in the second half of the season (153 sOPS+). Kyle’s postseason heroics are also of note here. He first struck in the third inning of the wild card game, sending a 3rd inning Gerrit Cole fastball high and deep into right field, sending Fenway into pandemonium, and increasing the lead to three runs. Then, in game three of the ALCS, Schwarber sent a similarly high and deep flyball again into right field. Once again Fenway was sent into a state of chaos, as not only did the Red Sox now lead 6-0, but they also became the first team in history to hit three grand slams in a single postseason.

3. Acquiring RHPs Nick Pivetta and Connor Seabold for Heath Hembree and Brandon Workman

The 2020 Red Sox stood to gain nothing by holding onto bullpen pieces, and Chaim Bloom wisely sold off Hembree and Workman, who were both due for free agency at season’s end. The duo joined a Phillies bullpen amid a historically bad season. They were not of much help. The two combined for an ERA of 9.27 across 22.1 innings. At the time, Nick Pivetta did not seem that impressive of a return. At the time of the trade, the 27-year-old had thrown nearly 400 innings across four different seasons, never posting an ERA+ above 86 in a calendar year. In his first full season in Boston, he looked like an entirely new pitcher. While his overall run prevention (104 ERA+) was only slightly above league average, it was still a vast improvement over the rest of his career. Additionally, he posted career bests in a variety of xStats, including xBA (.197), xwOBA (.279), and xERA (3.31). The other half of this return, Connor Seabold, ranks as the 11th best prospect in the system. While the righty lacks a true standout offering, he has strong command and four quality pitches. This, combined with his proximity to the Majors (expected to start 2022 in AAA after making his MLB debut in 2021), give Seabold a high floor as a fifth starter or longman in the bullpen. Even one of these pitchers in exchange for Hembree and Workman would have been enough for this trade to end up on the list, but getting both earns it a spot in the top 3, as well as the distinction of the highest-ranked trade made by Chaim Bloom.

2. 2020 Draft

One of the most surprising first-round picks in recent memory came from our friend Chaim Bloom. With his first selection ever, he drafted Nick Yorke, a high school second baseman from California. The pick confused analysts and fans alike. MLB Pipeline ranked Yorke as 139th prospect available in the draft, a far cry from the 17th overall pick the Red Sox used to draft him. Some of that confusion dissipated after their selection in the 3rd round, Blaze Jordan. The Mississippi State commit is one of the more famous high school baseball players in recent memory. Blaze has been in the national spotlight for his power since he was 11 when he won his first national home run derby. In 2019, at age 17, he won the high school home run derby at that year’s MLB All-Star Game. Jordan likely would have been selected much earlier, but it was widely believed that it would be difficult to pry him away from his commitment to play at Mississippi State. Bloom planned for this. After getting drafted higher than expected, Nick Yorke was willing to sign for well below the slot value of the 17th overall pick. Saving this money allowed the team to go overslot in their offer to Jordan, successfully luring the young slugger away from college.

Sox Prospects ranks Yorke and Jordan 3rd and 7th in the system respectively. Yorke has even cracked Pipeline’s top 100 prospects, ranked 96th after the 2021 season. Yorke spent 2021 validating Bloom’s decision to pick him first, as he slashed .325/.412/.516 across low and high A, while slugging 14 homers en route to being named the Red Sox 2021 Offensive Player of the Year. Blaze Jordan posted similarly impressive numbers across the Florida Complex League and Low A, slashing .324/.368/.590. The duo is still a couple of years away, with neither expected to make the Majors until 2024, although they could force their way through the system faster than that if they continue to hit everywhere they go.

1. Selecting Garrett Whitlock in the 2020 Rule 5 Draft

When I started this list, the first thing I did was pencil this in for the top spot. The rule 5 draft is likely both the least reliable and highest potential upside method of adding talent to your roster. The vast majority of teams won’t even make a selection in any given year, as most teams aren’t willing to sacrifice the roster spot. Bloom showed he wasn’t afraid to dip into the Rule 5 draft during 2019 when he selected Jonathan Arauz. While Arauz was a typical rule 5 selection, filling a utility bench role on a non-contending team, Bloom showed his acumen in this facet in 2020 when he selected Garrett Whitlock from the rival Yankees.

Whitlock, a starting pitching prospect, found a home in Boston’s bullpen, where he quickly established himself as a valuable, high-leverage option for multiple innings. In a bullpen that was shaky to begin with and had more questions pop up along the way, Whitlock was remarkably consistent. His 2021 was highlighted by his performance in the Wild Card game, where he shut the door on his former team’s season, jamming Gleyber Torres on a fastball, inducing a weak flyball to Hunter Renfroe for the final out.

Whitlock is still under team control for five more seasons, although that could change pending the ongoing labor negotiations. Bloom reiterated the point several times that the organization still views him as a future starter. His three plus pitches (four-seam, slider, change-up) make him well prepared for such a role. Whitlock will likely have every opportunity to be a starter in 2022, but Bloom is clearly prepared for him to continue his role in the bullpen if necessary, as he has brought in veteran rotation depth in Rich Hill, Michael Wacha, and James Paxton. While it’s not clear exactly what role he will be in, it is clear that Garrett Whitlock is going to be a valuable piece of the Red Sox moving forward, hopefully for a long time.


Matt O’Halloran is a junior mathematics major at the University of Massachusetts Lowell. He works in analytics with the school’s baseball program. He is a writer for Beyond the Box Score and an editor at Diamond Digest. He can be found on Twitter @matto20.