HINDSIGHT: Red Sox biggest off-season mistake last winter?
The hosts of the Bastards of Boston podcast each breakdown the one Red Sox move from last winter that they hated the most!
CODY PAULSEN:
The Red Sox did a whole lot of 'meh' in the offseaon. The O'Neil acquisistion didn't move the needle much, the Criswell signing looks better in hindsight than it did at the time, and the Chris Sale trade at least made sense when it happened.
While Sale has certainly overperformed this year, I don't think anyone could have predicted the type of season he is having. Grissom was a highly touted right handed bat that could play second, those fit a lot of needs for the Sox so it made a ton of sense.
The one that confuses me the most is the Sandlin for Schreiber trade. I can't wrap my head around trading a major leaguer for a prospect when the bullpen has been such a thorn in this team's side for so many years.
Schreiber is a serviceable reliever and enjoying a nice season in KC. Sandlin is a good starting pitching prospect, but ranks 14th in our system and in high-A.
This move signals to me more than anything that we weren't willing to compete for the postseason this year which disappoints me the most.
JEREMY SCHILLING:
With the hindsight of 66 games played to this point, the Chris Sale trade to the Atlanta Braves for Vaughn Grissom is my least favorite off-season move by the Boston Red Sox.
Add in the fact that the Red Sox are paying half of Sale's salary and I am sick to my stomach. Especially considering the fact that Boston is rolling out the combination of Cooper Criswell and a weekly bullpen game.
Sale is 8-2 with an ERA of 3.01 in twelve starts. Across 74.2 innings the lefty has struck out 92 batters with a WHIP of 0.94.
Add the Andrew Bailey effect and it is not difficult to imagine a world where Sale is recreating these stats in a Red Sox uniform.
Conversely, Grissom is hitting .148 in 81 at-bats with only three RBI's. He is getting on base at a .207 clip with an OPS of .367. Woof! Add in the fact that he was not available to start the season and is currently injured.
Obviously, it would have been tough to predict Sale's return to form in 2024. Additionally, with his history it is not hard to imagine a world where he still gets injured this season, but for now Sale pitching well for the Atlanta Braves stings, and is my least favorite move of the off-season.
JASON KELLY:
The Red Sox offseason lacked any sort of real action or intent to compete heading into the 2024 season.
There were multiple things the front office could have done differently to improve the roster heading into Spring Training. Instead, they decided to basically stand pat and only make a few minor additions to an already compromised roster.
However, I think the biggest regret of the offseason was only adding Lucas Giolito to the starting rotation mix.
After trading away Chris Sale, the Red Sox made themselves extremely thin in the rotation, and Giolito’s injury certainly showed that. With Houck, Bello, and Crawford all slated to exceed their usual innings output, the team should have added one or two more dependable arms to help shoulder the load.
Chris Sale is gone, Giolito is down for the year, and injuries along with regression are already creeping into the Red Sox rotation as we head towards the All-Star break.
For a team that was already projected to underperform, another injury or two in the already paper-thin starting rotation could lead to an epic midseason collapse.
CHARLIE SMITH:
The Sale-Grissom Deal!
Sending Chris Sale to ATL was always going to be seen as a good situation for one team and a prayer for another.
Being in the minority - I wasn’t thrilled about the move. Grissom had some upside, but had injury and fielding concerns. So far it’s amounted to one guy hitting .148 with three RBI’s, and one extra base hit and one bat flip.
Sale? Well he’s flipped the script with an 8-2 record, 3.01 ERA, and 92 strikeouts across 74 2/3 innings. Also only six HRs allowed.
What else? The Sox paid $17 million to NOT have Sale pitch in Boston.
Brutal!
TERRY CUSHMAN JR:
The Red Sox have flaws in nearly every aspect of their team. Only as of late, the starting pitching has started to sputter. The offense, however, has been the one constant problem all season long.
Justin Turner put together a strong 2023 campaign, essentially replacing the production we lost when J.D. Martinez departed the previous season.
My opinion all winter long was that Turner would need to be adequately replaced, with the ADDITION of another solid right handed bat. It was important to balance out the massive abundance of lefties.
What was Craig Breslow’s solution? Tyler O’Neill.
Everything that previously haunted the former Cardinals outfielder has followed him to Boston. The strikeouts. The injuries. The usual malfunctions that typically result in him having barely mediocre seasons.
Only Rafaela and Duran have more strikeouts than O’Neill. And why wouldn’t they? Since they both young outfielders have played a ton more games.
Besides hitting a meager .150 the entire month of May, he only has two home runs since April 27th.
The oft injured O’Neill has been a massive net negative to Turner, and without an additional impact right handed bat, how does this team finally gain its footing in a wildcard race?
Let’s also not fail to mention Boston has a pitching staff that desperately needs run support.
To add insult to literal injury, O’Neill has essentially destroyed his trade value as we head towards the trade deadline.


