If I had a nickel for every time someone asked me why I’m a Red Sox fan, I’d have a lot of nickels. Granted, being a fan of Boston sports while living in Chicago is pretty rare, but it is something I am very proud of since I was born there. While Boston is one of the most successful sports cities in the country, there is still so much pain that goes unnoticed.

There is so much that I could rant about the Red Sox’s management decisions in free agency and trades, but I am deciding to focus on two major ones: the Mookie Betts trade and the Rafael Devers trade.

It’s hard to describe just how bad the Mookie Betts trade was, but I’ll try to paint the picture as best I can.

Imagine this: you’re a nine-year-old kid watching your favorite baseball team win the World Series, your favorite player (Mookie Betts) wins the MVP, and the roster looks better than it ever has before. The next season, Mookie played amazingly again, batting .295, hitting 40 doubles, and even winning a Gold Glove along with all that. Being a gold glove winner means that analysts around the country consider you the best fielder at your position that season. You think that your team finally found their guy, and he’ll be on the team for his whole career and be one of the greats. But you’re wrong.

February 11, 2020. I remember that day like it was yesterday. I was eating my snack after my normal 4th-grade school day when my dad laid down the hammer. The Red Sox traded away their best player in at least 10 years to the Los Angeles Dodgers, along with one of their best relieving pitchers, David Price. This trade inevitably kick-started the Dodgers dynasty that we are all familiar with, but that’s a conversation for a different day.

In return for the 27-year-old MVP, the Red Sox received Alex Verdugo, Connor Wong, and Jerter Downs.

Alex Verdugo played 3 full seasons at the MLB level with Boston, hitting only .260 in his best season. Connor Wong played only 60 games last season, hitting .190, making himself one of the worst catchers in the MLB. Jeter Downs only played 14 games with the Red Sox, batting a pitiful .154.

These stats are not in-depth at all, but you can see just how little production they got in return for an MVP, 7x Silver Slugger, and 6x Gold Glove winner.

The Red Sox owner is one of the richest in all of sports. If you need proof, look up “John Henry Red Sox boat,” and that should give you a good perspective. If your owner has lots of money, you would think that he would spend it to better his team, especially if it’s to lock up the best player in the MLB at the time. Instead, he dumps all his money into Liverpool F.C in the Premier League, which he also owns.

Another time Henry decided not to spend his money was more recent, in the 2025 offseason, which was very uneventful for the Red Sox, thanks to Henry and Chief Baseball Officer Craig Breslow. The more recent things I blame Breslow for not getting the job done and being a horrible negotiator.

On January 13th, 2023, the Red Sox re-signed one of their biggest talents in 26-year-old Rafael Devers. Devers is a big, power-hitting third baseman who has been in Boston his entire career. He was loved by fans and loved the city of Boston. The Red Sox signed him for 13 years, and were paying him 313 million dollars. But in the offseason before the 2024-2025 season, the Red Sox signed star third baseman Alex Bregman.

This made Devers a little unhappy because they play the same position, and he didn’t want his spot to be taken away. So, to satisfy him, they moved Bregman to second base. Bregman is by far a better fielder than Devers, and definitely should’ve been playing third over him just because of that. The coaches knew this, and they made the switch to put Devers at DH and move Bregman back to third.

Designated hitter (DH) is probably the best position for Devers to play. Standing 6’ and weighing 235, he isn’t the most athletic guy on the field, but he sure does have pop at the plate.

When the first baseman for the Red Sox, Triston Casas, got hurt, the coaching staff asked Devers if he would be okay trying to play first base, but he refused. In Dever’s defense, this was the third time they changed his position. I would be a little ticked off, too. But in the end, you listen to your coaches, and Devers switched to first base.

Then things got crazy. Very fast.

I remember this day vividly as well. June 15th, 2025. I was driving home from my friend’s lake house when I got the ESPN notification from Jeff Pasan. The Red Sox traded Rafael Devers to the San Francisco Giants in exchange for James Tibbs III, Jordan Hicks, and Kyle Harrison.

James Tibbs never played in a game for the Red Sox, as he was traded to the Dodgers about a week later. Kyle Harrison has been pitching in the Minor leagues for half a season, but hasn’t been anything special. Jordan Hicks appeared in a few games for the Red Sox but was genuinely one of the worst pitchers I’ve ever watched. But it doesn’t even matter because he got traded to the White Sox about two weeks ago.

The trade caught everyone by surprise, and no one understood why the Red Sox had traded the guy they had basically marked as their future by signing him to that 13-year contract. The Red Sox management later stated that Devers felt like a “locker room cancer” to them, and he wasn’t benefiting the team in any way.

Moving on quickly from the unknown question of why they even traded him in the first place, they still had Alex Bregman, who was signed on a three-year deal, with opt-outs after every year. This means that if he plays really well and thinks he can get more money somewhere else, he has the chance to go do that.

And that is exactly what he did. Bregman played outstanding for Boston last season and thought he was worth more than what his contract was. The Red Sox still had a chance to re-sign him, but I had zero confidence they would get it done. As you can see, they have a tendency to let their eBay players walk away from them. And guess what, he did.

Alex Bregman signed with the Chicago Cubs for 175 million dollars. The Red Sox reportedly offered him 155 million, but didn’t believe his agents when they said they had a better offer, and let him walk away, just like they did with their other stars.

Bregman’s leaving was particularly harmful to the Red Sox because last season Boston started with 2 third basemen who were both ranked in the top 10 for their position, and starting this season, they have zero. Bregman was thought to be the leader of the team, providing the young core of the team with wisdom and experience, and was going to be the guy they stuck with. After all, they did trade away their power-hitting third baseman while he was in his prime for this guy.

The Boston Red Sox management has a history of making bad choices, and I can only hope that they will finally come to their senses and figure it out.