Red Sox: This winter will decide Chaim Bloom’s legacy in Boston

BOSTON, MA - DECEMBER 9: Chief Baseball Officer Chaim Bloom of the Boston Red Sox speaks during the 2019 Major League Baseball Winter Meetings on December 9, 2019 in San Diego, California. (Photo by Billie Weiss/Boston Red Sox/Getty Images)
BOSTON, MA - DECEMBER 9: Chief Baseball Officer Chaim Bloom of the Boston Red Sox speaks during the 2019 Major League Baseball Winter Meetings on December 9, 2019 in San Diego, California. (Photo by Billie Weiss/Boston Red Sox/Getty Images) /

Red Sox CBO Chaim Bloom must separate himself from ghosts of GMs past

This upcoming winter will be one that will set the tone for Chaim Bloom’s time with the Red Sox. We’ve seen with executives of the past that one transaction or one free agency window can cement their legacy, good or bad. I’m not going to this past offseason against Chaim as he was brought in to achieve a very specific goal, and though I hate how he had to go about it, he achieved what he was asked to do.

But now the game has changed and his adaptability is what will seal his fate in the minds of Red Sox Nation. Before I put the full focus on Chaim, let’s take a walk down memory lane with some of our previous GMs.

When I think of Theo Epstein two things come to mind, signing David Ortiz and Thanksgiving at Curt Schilling‘s house. The former would become one of the greatest players to ever wear a Red Sox uniform, and the latter would be the key component in ending Boston’s World Series drought. Epstein would prove to be one of the best GMs in the game during his time in Boston and has continued that success in Chicago.

The next stop on our trip will be to visit with our old friend Ben Cherington. Pittsburgh’s GM was the heir apparent to Epstein and had mixed success in the role. He was a damn wizard when it came to drafting young talent and building the farm system. Guys that he either brought into the system or developed during his time played a big role in the Red Sox winning the World Series in 2018.

However, it was the awful contracts that he gave to Pablo Sandoval and Hanley Ramirez that will haunt him forever. Neither player panned out to the salaries that they were given and the Red Sox have been paying for those mistakes long after Cherington’s departure. Sadly, for as great as he was in regards to building toward the future, he couldn’t match that excellence on the free-agent market.

Finally, we’re going to call up the man that got the final pieces needed to create the juggernaut that was the 2018 Red Sox, Dave Dombrowski. Dealin’ Dave was brought in by the ownership to do what he does best, trade top prospects for superstars, and spend on big-name talent. He did exactly that by creating blockbuster trades for Craig Kimbrel and Chris Sale. He’s also the man that brought J.D. Martinez to Boston and extended Xander Bogaerts ahead of 2019.

Unfortunately for all the good that Dombrowski achieved, he also lived up to his reputation on the other side of the coin. He gutted the farm system and set Boston’s prospect list back a few years, hindering several promotions.

Towards the end of his time with the organization the ownership made it seem as if he was acting all on his own just dolling out contracts, not accepting any of the blame. Dombro was made to be a scapegoat for the incredibly disappointing 2019 season and was sent packing before it came to an end.

Enter, Chaim Bloom.

Chaim Bloom can cement his Red Sox legacy this offseason

Time to sound dramatic, this offseason will be do or die for Chaim Bloom’s time in Boston. Ok, now that we’ve got that out of the way let me get into why I feel this way. In his first winter with the Red Sox he was brought in for one reason and one reason only, shave the budget. The team was at the highest level of the CBT penalty and needed to get back below the marker in order to reset their clock.

As I said above, he achieved the task he was given and did what his bosses asked him to, but he had to trade away a generational talent and a former Cy Young winner to do so. Well, he didn’t need to trade away Mookie Betts, but that’s a conversation for another time. I don’t hold that against him though as it felt like the Red Sox were never truly willing to play ball with the former MVP and he was going to get traded no matter what.

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So this upcoming offseason will be the first true test of Chaim as the boss of a baseball ops team. While he was in Tampa he was high on the food chain but he wasn’t the top dog, it’s a very different situation for him in Boston. He needs to attack this free agency window and offseason like a shark smelling blood in the water.

The biggest need on the to-do list is pitching. Even with Chris Sale and Eduardo Rodriguez set to return in 2021, this pitching staff is still a massive embarrassment. He should be willing to not only spend on the free-agent market but also listen to trade offers in order to obtain a solid starter and quality reliever. If he can achieve those things while not giving away idiotic contracts like those before him, I think it’ll be a massive step in a positive tenure.

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His eye for talent and player development will be a strong boost for the Red Sox from their previous front office boss. I truly believe that he can partner that skill for building a farm system with the massive budget he now has in Boston. In his first offseason, he was mandated, whether FSG wants to admit it or not, to cut the budget. Now that they’re back in the good graces of the finance department, he can spend on the pieces he feels will fix this team ahead of 2021. With a great eye for talent and a budget to match, I think Chaim Bloom can thrive at Fenway Park.