In 2019 he was again an All Star, led the AL in walks and WAR, and received the 2019 American League Silver Slugger Award at third base.

[2][3] At age 13, in his Bar Mitzvah speech he said: "I want to be a professional athlete who plays for the love of the game, never quits trying to give my best, and is a good role model for all of the kids who look up to baseball players.

[15] His great-grandfather Samuel "Bo" Bregman immigrated from Russia to Washington, D.C., around 1900 at age 11 to escape Russian anti-Jewish pogroms, and ultimately married Sadie Hurwitz.

In his first game, he turned an unassisted triple play by catching a line drive, tagging a runner, and then stepping on second base.

[7][14][27][28] At the October 2010 COPABE Pan American Baseball Championships in Lagos de Mareno, Mexico, while he was a sophomore, he batted .564 for the gold-medal-winning 16-and-under USA National Team, and was named the MVP.

[7] In the fall of that year he led the 18-and-under U.S. National Team to a gold medal at the International Baseball Federation World Championships.

[7][12][38][39][40] Moreover, he was named 2013 ABCA First-Team All-South Region, National Collegiate Athletic Association (NCAA) Baton Rouge Regional Most Outstanding Player, Louisiana Freshman of the Year, and SEC Player of the Week (March 25, 2013), and named to the 2013 USA Collegiate National Team (for which he batted .361).

[48][49][50][51] He was one of four finalists for the 2015 Golden Spikes Award, presented annually to the nation's top college player and won by outfielder Andrew Benintendi.

[63] He made his professional debut with the Quad Cities River Bandits of the Single-A Midwest League in late June.

[73] During the May 14, 2017, game versus New York at Yankee Stadium, Bregman hit his first major league grand slam, off Masahiro Tanaka, in the first inning of a 10–7 Astros win.

[77][73] Houston won the AL West division with a 101–61 record, thus advancing Bregman to his first career major league playoff.

In Game 7, with the Astros up 1–0 with Yankees on first and third in the top of the fifth, Bregman threw out Greg Bird at home on a chopper to third off the bat of Todd Frazier to help preserve the lead.

Bregman would once again throw out a runner at home from third base in Game 4 of the World Series against the Los Angeles Dodgers when he gunned down Austin Barnes at the plate in the top of the sixth inning to preserve a scoreless tie.

[93] After he hit a go-ahead home run in the 10th inning off Ross Stripling, he was named the Astros' first All-Star Game MVP.

[94][95] In the second half of the season, Bregman became the focal point of the Astros offense as injuries to Carlos Correa, George Springer, and Jose Altuve took all three of them out of the lineup for most of July and early August.

[73] During this stretch, the Dugout Stare, a home run celebration that Bregman had begun performing during the 2017 postseason, became popular among his teammates and on social media.

In a game against the Seattle Mariners on August 22, Tyler White hit a solo home run in the top of the 9th inning of a 10–7 win.

A large group of Astros players, including Bregman, performed a synchronized dugout stare into the camera, eventually becoming their new team home run celebration.

[77][95] Bregman batted .386/.488/.735 with runners in scoring position, the highest slugging percentage in the major leagues and the second-best OPS (behind Mike Trout).

[77] In the 2019 postseason, Bregman enjoyed an excellent ALDS against the Tampa Bay Rays, batting .353/.450/.647 with two doubles, one home run, three walks, and two RBIs.

Bregman's bat went ice cold in the ALCS and first three games of the World Series, though, as he struggled through a 4-for-31 (.129) slump with only one home run and three RBIs.

[127] On June 16, 2021, Bregman strained his left quadriceps in a game versus the Texas Rangers, as he attempted to avoid hitting into a double play.

[125] For his meritorious character and service to the community, the Houston chapter of the Baseball Writers' Association of America (BBWAA) honored Bregman with the Darryl Kile Good Guy Award for 2021.

[137] Bregman doubled and drove in two runs on September 19 versus the Rays to power a 4–0 Astros' win that clinched a fifth AL West division title over the previous six seasons.

[140] Bregman was also one of two qualified batters in the majors to collect more walks than strikeouts while hitting at least 20 home runs, alongside Juan Soto.

The pair combined to lead the Astros to 5 wins in 6 games; Bregman batted .444, 1.389 OPS, three doubles, three home runs, three walks, and six RBI.

This was the second occurrence in club history with co-Players of the Week; on September 10, 2000, Richard Hidalgo and Julio Lugo shared the honors.

[77] Following the season, Bregman became a free agent[160] after rejecting a one year, $21.05 millon qualifying offer from the Astros,[161] and was named AL Gold Glove Award winner at third base for the first time.

[162] On February 15, 2025, Bregman signed a three-year, $120 million contract with the Boston Red Sox, including opt-out options after the 2025 and 2026 seasons.

[169] With several Astros teammates of Latin descent, including Jose Altuve, Yordan Alvarez, and Yuli Gurriel, Bregman consistently practices and improves his Spanish-speaking ability.