Boston Red Sox 2015–2017 The
Boston Red Sox chose Benintendi with the seventh overall selection in the
2015 MLB draft. He signed with the Red Sox, receiving a $3.6 million
signing bonus. Benintendi made his professional debut with the
Lowell Spinners of the
Class A-Short Season New York–Penn League. Andrew finished the 2015 season playing 19 games for the Class A Greenville Drive going 26/74 (.351) and posting an OPS of 1.011. He began the 2016 season with the
Salem Red Sox of the
Class A-Advanced Carolina League and received a promotion to the
Portland Sea Dogs of the
Double-A Eastern League on May 15. The Red Sox promoted Benintendi to the major leagues on August 2, 2016, straight from Double-A, only 421 days after being selected in the draft. He made his major league debut on August 2, against the
Seattle Mariners as a
pinch hitter, and recorded his first major league hit off of
Hisashi Iwakuma on August 3. Benintendi recorded both his first major league
triple and home run against the
Detroit Tigers on August 21 in a 10–5 loss. On October 6, in Game 1 of the
2016 ALDS against the
Cleveland Indians, Benintendi hit a home run in his first postseason at bat, off of Indians' pitcher
Trevor Bauer. With the feat, Benintendi became the youngest Red Sox player to hit a home run in a postseason game. However, the Indians won the game by a score of 5–4 and swept the series in three games. Benintendi ended the
2016 season with a .295 batting average, 31 hits, 14 RBIs, two home runs, and one stolen base in 34 games played. Benintendi started 2017 on the Red Sox'
Opening Day roster, batting second as Boston defeated the
Pittsburgh Pirates by a score of 5–3. On July 4, against the
Texas Rangers, Benintendi went 5-for-5 with 6 RBIs, two home runs, and a double in the 11–4 victory. He finished second in the
American League Rookie of the Year voting, despite receiving no first-place votes due to
Aaron Judge winning unanimously. Overall, during the
2017 Red Sox regular season, Benintendi batted .271 with 20 home runs, 90 RBIs and 20 stolen bases in 151 games played. In the
ALDS against the eventual
World Series champions, the
Houston Astros, he batted .250 (4-for-16) with a home run and two RBIs in four games.
2018–2020 Through the first half of the 2018 season, he was the team's regular left fielder, usually batting second, behind
Mookie Betts. On July 8, Benintendi was named as a candidate in the American League's
All-Star Final Vote for a spot in the
2018 MLB All-Star Game. At that time, Benintendi had a
slash line of .293/.379/.515 with 14 home runs and 55 RBIs. Instead, fans voted in
Jean Segura of the
Seattle Mariners. For the season Benintendi appeared in 148 games hitting .290 with 41 doubles, 103 runs scored, 16 home runs, 87 RBIs, and stealing 21 bases. In the
MLB playoffs, Benintendi recorded the final outs to seal victories for the Red Sox in Games 4 and 5 of the
American League Championship Series, the first of the two a diving effort to prevent a bases-loaded hit in a two-run game. The Red Sox won the
World Series over the
Los Angeles Dodgers, giving Benintendi a championship title. In the World Series, Benintendi had four hits in Game 1 and hit .333 in series. Benintendi began the 2019 season as Boston's regular left fielder. Manager
Alex Cora initially made him the team's
leadoff hitter, until the start of June when Cora moved Benintendi to second in the order, with
Mookie Betts batting first, as was the team's usual order in 2018. On June 11, Benintendi was
ejected for the first time in his MLB career for a comment he made about home plate umpire
Ángel Hernández that was heard by first base umpire
Vic Carapazza. For the season, Benintendi appeared in 138 games, batting .266 with 40 doubles, 13 home runs and 68 RBIs. On February 8, 2020, the Red Sox announced signing Benintendi to a two-year contract worth $10 million, avoiding arbitration. On July 29, he recorded the 500th hit of his major league career, a
ground rule double off of
New York Mets pitcher
Jeurys Familia. Benintendi was placed on the 10-day
injured list on August 12, with a right rib cage strain. Benintendi's 2020 campaign came to an end on September 8, after being transferred to the 45-day injury list. With the
2020 Red Sox, Benintendi was 4-for-39 at the plate (.103) with one RBI.
Kansas City Royals (2021–2022) On February 10, 2021, the Red Sox traded Benintendi and cash to the
Kansas City Royals as part of a three-team trade in which the Red Sox acquired
Franchy Cordero,
Josh Winckowski, and three
players to be named later (identified in June as minor league prospects: outfielder Freddy Valdez from the
New York Mets, and pitchers Grant Gambrell and Luis De La Rosa from the Royals) while the Mets received
Khalil Lee. In his first year with the Royals, Benintendi batted .276/.324/.442 with 17 home runs and 73 RBIs in 134 games. He led all left fielders with 1,116 innings played and a .987 fielding percentage, and won his first
Gold Glove Award. In
salary arbitration, Benintendi was awarded a salary of $8.5 million for the 2022 season. He began the season batting .317 en route to being named the Royals' lone representative to the
2022 MLB All-Star Game. In July 2022, Benintendi was one of several Royals players who was unable to play against the
Toronto Blue Jays due to Benintendi's refusal to be vaccinated against the COVID-19 virus (and would have been denied entry to Canada due to health requirements at the time). In 93 games with Kansas City prior to being traded, Benintendi batted .320/.387/.398 with 3 home runs and 39 RBIs.
New York Yankees (2022) On July 27, 2022, the Royals traded Benintendi to the
New York Yankees in exchange for minor league prospects
T. J. Sikkema,
Chandler Champlain, and
Beck Way. On September 2, 2022, Benintendi was hit by a pitch on the right wrist and left the game. The next day, he was put on the 10-day injured list due to right wrist inflammation. Further evidence revealed that Benintendi had broken the hamate bone of his right wrist, which required surgery. In 2022 with the Yankees he batted .254/.331/.404 with 2 home runs in 114 at bats.
Chicago White Sox (2023–present) On January 3, 2023, Benintendi signed a five-year, $75 million contract with the
Chicago White Sox. Benintendi hit his first home run with the White Sox on June 16 against the
Seattle Mariners off of
Bryan Woo. In 2023, he batted .262/.326/.356 with five home runs and 45 RBI in 562 at-bats while leading all AL left fielders with four errors. Benintendi had a power resurgence in the 2024 season, hitting 20 home runs to match his career high set in 2017. However, by other metrics, 2024 was Benintendi's least productive season. His batting average (.229) and on-base percentage (.289) were career lows for a full season. Coupled with below-average defense in left field, Benintendi registered a negative
wins above replacement for the first time in his career, excluding the 2020 COVID-shortened season. On February 27, 2025, it was announced that Benintendi would miss 4-6 weeks with a non-displaced fracture in his right hand, an injury suffered when he was hit by a pitch during a spring training game. He returned in time for opening day on March 27, hitting a three-run home run in the White Sox's 8–1 win over the Angels. On March 31, Benintendi hit his 100th career home run with a 3-run home run off
Minnesota Twins starter
Chris Paddack. On April 9, Benintendi was placed on the 10-day injured list due to a
left adductor strain. He made his return on April 17 versus the
Athletics where he went 0–of–2. On April 18, 2025, Benintendi recorded his 500th RBI when he hit a solo home run off of
Hunter Dobbins in the top of the fourth inning. On May 7, Benintendi was placed on the 10-day injured list for the second time in the season due to a
left calf strain. He made his return on May 23 versus the
Texas Rangers where he went 0–of–2 with a RBI walk. On September 23, the White Sox announced that Benintendi was suffering from left
Achilles tendinitis and would miss the rest of the regular season. He finished the season with a .240 batting average, 20 home runs, 63 RBI, and a .738 OPS in 116 games. ==Personal life==