How Boston Red Sox Fumbled Signing Former Astros Slugger 13 Years Ago

Alex Bregman’s return to the Boston Red Sox was, in a sense, a call-back to when the franchise blew their chance back in 2012.

Matthew Postins | Feb 17, 2025

Sep 4, 2024; Cincinnati, Ohio, USA; Houston Astros third baseman Alex Bregman (2) high fives teammates after scoring on a RBI single hit by outfielder Ben Gamel (not pictured) in the second inning against the Cincinnati Reds at Great American Ball Park. / Katie Stratman-Imagn Images

In this story:

Houston Astros

Houston Astros fans aren’t going to forget Alex Bregman’s contributions to the franchise since he was selected in the first round out of LSU in 2015.

Now that he’s with the Boston Red Sox, the Astros will only see him in a visiting uniform. But it could have gone much differently.

No, not in free agency. Way back in 2012 when Bregman was still in high school.

Back then, he was playing at Albuquerque Academy in Albuquerque, N.M. But he wasn’t highly touted. But, he was drafted in the 29th round by the Red Sox. Yes, the Red Sox.

Bregman could have been theirs back then. But, as The Athletic reported, there was one reason why Boston didn’t get a deal done.

Money. Isn’t that always the way?

Back in 2012, franchises were dealing with a soft cap on draft signing bonus pools for the first time. Boston took a shortstop in the first round and then paid over-slot bonuses to two other draft picks.

After that, Boston was basically out of money.

Amiel Sawdaye was Boston’s amateur scouting director at the time. Today, he is Arizona’s assistant general manager. Sawdaye said to The Athletic that he felt Bregman should have been drafted far higher, perhaps as high as the third round. But, he broke his right middle finger and missed his senior season.

Once he was healthy and he worked out for scouts before the draft, Boston’s scouts were enamored. One, Jim Robinson, told Sawdaye that Bregman was the best shortstop in the class.

But, none of it was to be. Bregman didn’t sign with Boston, went on to LSU to play for the Tigers and eventually was the Astros’ first-round (No. 2 overall) pick in 2017. The Red Sox took outfielder Andrew Benintendi five picks later.

Boston did all right. The Red Sox won the 2018 World Series, one year after the Astros won their first world championships — with Bregman at third base.

Bregman made his MLB debut in 2016. He has a career slash line of .272/.366/.483/.848 with 191 home runs and 663 RBI. He made two All-Star Games, won the Gold Glove last year and finished second in American League MVP voting in 2019.

While with Houston, the franchise won two World Series, made two other World Series appearances, went to the AL Championship series seven times and went to the playoffs eight times.

Recommended Articles