Adley Rutschman is hitting .170 as a Red Sox, and his elbow is acting up.
Am I sounding the alarm?
Not yet.

Boston gave up a massive prospect haul for him. Maybe this is the move that pushes the Red Sox over the top. Maybe years from now we're watching those prospects become stars and wondering what the hell Craig Breslow was thinking.

We don't know yet.

Nomar taught me that.

It has been 22 years since Nomar Garciaparra last played for Boston, and no move hit me harder.
I can still see the batting gloves. The toe taps. No. 5 everywhere.

Then he was gone.

I was a kid. I just knew Orlando Cabrera was playing shortstop now, so naturally I hated him for not being Nomar.
A few months later, Cabrera helped Boston win the World Series.

Sports are stupid. And wonderful.

Sometimes they take Nomar away. Sometimes Minnesota gives up on David Ortiz and Boston gets Big Papi for $1.25 million.

Manny launching balls over the Monster. Lester beating cancer, becoming an ace and winning championships. Xander growing up here. Mookie becoming an MVP and feeling untouchable.

Eventually, one way or another, they were all gone.

Sometimes it was right. Sometimes it absolutely wasn't.

And sometimes you pay Pablo Sandoval $95 million for 161 games and 14 home runs.

Adley can sit this one out…for now.

For the top five and bottom five, let’s keep it to the last 10 years. Although the scars go back much further.

The Best
1. Trading for Chris Sale, December 2016
Boston dealt Yoan Moncada, the No. 1 prospect in baseball, Michael Kopech and two others for one of baseball's nastiest pitchers.
Sale struck out 308 batters his first year in Boston and finished second in Cy Young voting.
A year later, he struck out Manny Machado for the final out of the World Series.
Prospects are fun. Championships are forever.

2. Signing J.D. Martinez, February 2018
Spring training had started and somehow J.D. Martinez was still unsigned.
Boston grabbed him. He hit .330 with 43 bombs and 130 RBI.
The Red Sox won 108 games and the World Series.
Sometimes the obvious move is obvious for a reason.

3. Trading for Nathan Eovaldi, July 2018
Boston gave Tampa Bay Jalen Beeks, Baseball America's No. 6 prospect in the system at midseason, for Nathan Eovaldi.
Then October happened.
Eovaldi threw six relief innings in that insane 18-inning World Series loss and became a Boston sports folk hero.
He stayed five seasons and became the guy you wanted on the mound in October.

4. Stealing Garrett Whitlock From the Yankees, December 2020
The Yankees developed Garrett Whitlock.
The Yankees left him unprotected.
Boston paid them $100,000 and took him.
He immediately became one of our best relievers.
A big-league weapon for $100,000, directly from the Yankees.
Beautiful.

5. Getting Wilyer Abreu, August 2022
Boston moved an expiring Christian Vázquez to Houston and got two prospects back.
One became Wilyer Abreu, now a two-time Gold Glove winner.
That's how deadline selling is supposed to work.

The Worst

1. Trading Mookie Betts, February 2020
Mookie Betts was 27, an MVP, a World Series champion and one of the best players alive.
The Boston Red Sox traded him anyway.
Spare me the payroll math.
Mookie should have retired in Boston.
And the longer he stays in Los Angeles, the more his Red Sox years start to feel like the first chapter of someone else’s legend.
That makes me sick.

2. Trading Rafael Devers, June 2025
Boston finally paid the homegrown superstar.
Ten years. $313.5 million.
Then, barely a season and a half into the extension itself, they moved him off third, turned a position change into a public feud and traded him to San Francisco.
Apparently the lesson from Mookie had an expiration date.

3. Letting Xander Bogaerts Walk, December 2022
Boston was probably right.
Would I want Xander's $280 million contract today? No.
Did I enjoy watching a two-time champion and franchise cornerstone put on a Padres uniform?
Also no.
Not every painful move is stupid.
Some just suck.

4. Letting Kyle Schwarber Walk, November 2021
How did we fuck this one up?
Schwarber came here, mashed, helped push Boston to the ALCS and looked genetically engineered for Fenway.
Boston let him leave.
Then he became one of baseball's premier power hitters, eventually launching 56 homers and finishing second in MVP voting in 2025.
Who could have seen that coming?
Besides everyone.

5. Letting Nathan Eovaldi Walk, December 2022
We knew exactly who Nate Eovaldi was.
October legend. Big-game pitcher. Beloved here.
Boston let him leave.
His first season in Texas ended with another World Series championship.
Cool. Very cool.

Honorable mention to Chris Sale, because watching him leave after years of injuries and immediately win a Cy Young was cruel, even if trading him was completely defensible.

Who did I miss?
Maybe Xander doesn't belong. Maybe Whitlock isn't big enough. Maybe I left out the one that still makes you irrationally angry.

Who belongs on this list?

And who are you kicking off?