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It Cannot Be That Hard To Be a General Manager

It just can’t!

Boston Red Sox End Of Season Media Availability Photo by Billie Weiss/Boston Red Sox/Getty Images

Listen, I’m not naive. I know that it’s probably pretty hard to be a GM/President of Baseball Operations/Chief Baseball Officer. Actually, before I get into this, let’s talk about those titles. Why do teams have both of those things now? What is even the difference? Why was Theo Epstein the Red Sox’ General Manager and then Dave Dombrowksi was their President of Baseball Operations but now Chaim Bloom is the Red Sox Chief Baseball Officer? They were/are all at the top of the chain of command! What is the difference?! And, even if a team has a Chief Baseball Officer or President of Baseball Operations, they still have a GM! What does that person even do? It’s all a big racket if you ask me. Anyway, where was I?

Red Sox GM Theo Epstein And Manager Terry Francona Photo by Jim Davis/The Boston Globe via Getty Images

Okay right, yeah. This is a long-held belief of mine: it just simply cannot be that hard to be a GM (we’re gonna roll with that one for the purpose of this piece because it’s shorter to type). Think of the vast amount of information at the hands of every MLB team these days. There are teams upon teams of people who provide information so that front offices can make the best decision possible. Now, sure, not every team can be great. Somebody’s gotta win and somebody’s gotta lose.

On the flip side of that, GMs who are paid millions of dollars to do their job should never lose trades. I’m not talking deadline deals for rentals where teams overpay for a guy for 2 months. That happens and it’s a part of the game. I’m talking about your everyday offseason trade, that kind of thing. Free-agent signings are a whole other thing.

This brings me to a man named Chaim Bloom. Since he was hired by the Red Sox after the 2019 season, Chaim has made 32 trades. Of those trades, I would probably categorize 13 of them as “major” trades. Of those 13 “major” trades, Chaim has “won”, and I’m being generous here, 4, MAYBE 5 of them. Let’s break some of them down.

The Mookie trade. I don’t need to get all the way into this because, really, none of us need that. All I’ll say is this was unmitigated disaster. Jeter Downs is gone. Connor Wong is maybe a backup catcher. And Alex Verdugo has gotten worse every year in Boston. Unless Verdugo takes a colossal step forward this year, this is a pitiful return for arguably the second greatest player in franchise history.

Next up, we have Chaim’s best trade: Brandon Workman and Heath Hembree for Nick Pivetta and Connor Seabold at the 2020 trade deadline. Credit where credit is due, this was a fleecing for Chaim. Getting back two controllable starters, regardless of their ability, for roughly 30 games of 2 relievers (who by the way, were both terrible post-trade) is fantastic.

Division Series - Tampa Bay Rays v Boston Red Sox - Game Three Photo by Billie Weiss/Boston Red Sox/Getty Images

One of the strangest trades Chaim’s made is the Andrew Benintendi trade. The Red Sox acquired Franchy Cordero, Josh Winchowski, and 3 PTBNLs (who are all still quite young, so maybe they become something) for Andrew Benintendi. Was Benintendi’s time in Boston probably up? Sure. But why trade him after his value completely cratered? Why not at least see if he could rebuild some of that value? It literally could not get worse than it was at the end of the 2020 season. Now, Cordero is gone and Winchowski was far and away the least impressive young arm the Sox had to use last year. This one never made sense to me.

Next up, one that will never really make sense to me. The Red Sox traded Hunter Renfroe to the Brewers for Jackie Bradley Jr, and prospects David Hamilton and Alex Binelas. Now, I got the idea behind this trade. Renfroe was coming off a career year and Chaim was still trying to build the farm back up. Where this deal goes awry is the inclusion of Jackie Bradley Jr. Let’s get one thing clear, I adore JBJ. He was a vital part of a championship here and I’ll always be grateful for that. That being said, it was insane that Chaim agreed to take him back in this deal. JBJ’s AAV of 12 million was ludicrous for the player he was/is now. That money being on the books is also a part of why the Red Sox stayed over the luxury tax in ’22, which is a whole other thing.

American League Championship Series Game 4: Boston Red Sox v. Houston Astros

Let’s give Chaim a win here. At the 2022 deadline, he traded Jake Diekman to the White Sox for Reese McGuire. How Chaim convinced Chicago to take on Diekman’s contract AND get back a decent player in return is genuinely impressive. Kudos on this one, Chaim.

It seems evident to me after three years of Chaim that he can do pretty well on the smaller deals, but when he’s tasked with a big one, it’s probably not gonna go great. Thankfully, the Red Sox don’t have a franchise player that might need to be traded soon. Wait, hold on everyone. Somebody’s tugging on my arm.

Tampa Bay Rays v Boston Red Sox Photo By Winslow Townson/Getty Images