On Monday morning, the Red Sox announced J.D Martinez, who signed a 5-year, $110 million contract. I’m surprised Scott Boras settled, but he probably realized Martinez wasn’t going to get the $200 million they were looking for.

Am I excited he’s on the team? Sure. He had pretty good numbers last season—.303 average, 45 home runs, 104 RBI, .690 slugging—but there are a few things that are nagging me about this signing:

1. He’ll be turning 31 this year: Hypothetically speaking, if he stays in Boston for all five years, he’ll be 35. I’m assuming the Sox will have him DH, which will work better as he gets older.

2. He’s had some injuries: I get that players get hurt—that’s what’s going to happen when you play almost every day for six months. During his physical, an x-ray showed the presence of a condition involving the Lisfranc ligament in his right foot, an injury that landed him on the DL for the first six weeks of last season. Back in 2016, he also suffered a non-displaced fracture in his right elbow caused by running into the outfield wall. He says he’s healthy but the Sox are a little leery, especially when it comes to his contract.

If he’s going to DH, well, then there are no walls for him to run into.

3. The Sox have a horrible track record with free agent five-year contracts: Sorry, this is the cynic in me, but it’s one of the first things I thought of when I heard Boras was looking for five years.

Let’s take a trip down memory lane, shall we?

Daisuke Matsuzaka, 2007: The Sox won bidding right to him with a final bid of $51,111,111.11. The team wined and dined him and got him to sign a 6-year, $52 million contract. And things looked good. (They better have—the Sox just spent over $100 million on him.)

He finished 2007 with a 15-12 record, 4.40 ERA, and a World Series ring. His 2008 looked better with a final record of 18-3 and 2.90 ERA.

Then he played in the 2009 World Baseball Classic, had weakness in his arm—I also remember there might have been something with his back—and things were never the same.

He missed the first month of the 2010 season, did okay, had Tommy John in 2011, played in the minors for part of 2012, then agreed to a minor league deal with the Indians in 2013.

Now he’s back playing in Japan. We got two good years out of him.

Carl Crawford, 2011: Probably one of the worst signings in recent years. The Sox were like “Here’s $142 million! Come play with us for seven years!” and Carl said, “Sure! What can go wrong?”

Everything.

Over his first two seasons, he hit .260 with 9 home runs and 23 steals. AND THEY WERE PAYING HIM $20 MILLION A YEAR.

He was then part of a fire sale in 2012 along with Adrian Gonzalez, Josh Beckett, and Nick Pinto to the Dodgers. The Sox only had him for about a season and a half.

In case you were wondering, he’s retired now. I never knew that.

Pablo Sandoval, 2015: I lied before. THIS was the worst signing in recent years.

This time around, the Sox were making it rain $90 million for five years. (And lucky him, he got a sixth-year club option, too!)

In 2015, he batted .245 with 10 home runs and 47 RBI, career lows since his first full season in 2009.

He was overhyped and definitely not who the Sox thought they were getting for that price. And there was that whole Instagramming from the clubhouse problem in June of that season. He was benched after it was discovered he was liking pictures of women during a game in Atlanta. Claiming he was in the bathroom wasn’t a good enough excuse, but he wasn’t fined by the league.

Come spring training in 2016, Sandoval reported out of shape, and every sports outlet was commenting on his weight like a Kardashian pregnancy. As a result, he lost his starting job to Travis Shaw—who I’m still mad that the Sox traded for a lousy reliever who’s on the DL. But Sandoval did get one start that season in the beginning of April in Toronto, which featured the “Snap Heard Around the World.”

Conveniently, four days later Sandoval claimed he had “shoulder soreness,” and no one could figure out how he got hurt. It’s not like he really played at all. So to make it seem like a legitimate injury, the Sox placed him on the 15-day DL before having an MRI exam on his left shoulder. Enter Dr. James Andrews, the miracle worker of Tommy John surgeries. In the beginning of May, Sandoval underwent surgery to repair a torn labrum in his left shoulder.

It took the Sox another season before realizing that Sandoval wasn’t going to cut it. They said, “Pack your bags” and released him in July 2017.

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So, yeah, I’m a little hesitant when it comes to J.D. Martinez because of the bad life choices made by the Sox in the past. But I’m going to stay optimistic for now. Check back with me at the end of the season.