If you were watching baseball in 2016, Andrew Benintendi felt like the "Chosen One." He was the smooth-swinging lefty with the perfect hair who jumped from the draft to Fenway Park in what felt like a blink. Honestly, it’s wild to look back at how fast it all moved. Most fans remember him as a Red Sox cornerstone, but the journey since Boston has been a whirlwind of trades and record-breaking contracts.
You’ve probably seen the highlight reels of his snag in the 2018 ALCS. It's iconic. But if you try to map out exactly when he swapped the Sox for the Royals, or how long he actually spent in Pinstripes, things get a bit fuzzy for the average fan.
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Boston Red Sox: The 421-Day Sprint
Everything started in 2015. The Red Sox took Benintendi with the 7th overall pick out of the University of Arkansas. He wasn't just some prospect; he was the Golden Spikes winner. Basically, the best college player in the country.
Most guys spend years grinding in the minors. Not Benny.
Andrew Benintendi joined the Red Sox on August 2, 2016. Think about that. He was drafted in June 2015 and was starting in left field at Fenway just 421 days later. He made his debut against the Seattle Mariners as a pinch hitter. The hype was real. He stayed in Boston through the 2020 season, winning a World Series ring in 2018 and cementing himself as part of that legendary "Win, Dance, Repeat" outfield.
But baseball is a business. By late 2020, his production had dipped. The batting average plummeted to .103 in a weird, injury-shortened season. Suddenly, the "untouchable" prospect was on the block.
The Kansas City Pivot
On February 10, 2021, the news broke. Benintendi was headed to the Kansas City Royals. It was a massive three-team trade involving the Mets.
Kansas City was a fresh start. He wasn't the "next big thing" anymore; he was a veteran looking to find his swing again. It worked. In 2021, he went out and won a Gold Glove. He proved he wasn't just a Fenway product who benefited from the Green Monster.
He stayed with the Royals through the first half of 2022. He was actually their lone All-Star that year. He was hitting .320, looking exactly like the player Boston thought they had years prior. But the Royals were rebuilding, and Benintendi was a valuable chip.
The New York Yankees: A Short Summer
This is the part everyone forgets. Or maybe they just blocked it out.
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Andrew Benintendi joined the New York Yankees on July 27, 2022. The Yankees sent three prospects to Kansas City to get him. They needed a high-contact lefty for a postseason run. It looked like a match made in heaven. Then, the bad luck hit.
In early September, he broke a bone in his wrist on a swing. Just like that, his time in New York was effectively over. He only played 33 games for the Yankees. He never even got to play in the postseason for them. Because he was an impending free agent, he hit the market that winter without ever really "becoming" a Yankee.
Chicago White Sox: Making History
When the 2022 offseason rolled around, people expected him to sign a decent deal. Nobody—and I mean nobody—expected him to break records.
On January 3, 2023, Benintendi officially signed a five-year, $75 million contract with the Chicago White Sox.
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At the time, it was the largest contract ever handed out by the White Sox. Sorta crazy, right? A franchise that’s been around since 1901 had never given $75 million to a single player until Benintendi.
He’s been on the South Side ever since. 2023 was a bit of a struggle for him, and the team was, frankly, a mess. But 2024 saw a power surge where he hit 20 home runs, matching his career high. As of 2026, he’s still the primary left fielder for the Sox, under contract through 2027.
Andrew Benintendi Career Timeline at a Glance
To keep it simple, here is how the movement actually happened:
- June 8, 2015: Drafted by Boston (7th overall).
- August 2, 2016: Called up to the Big Leagues (Red Sox).
- February 10, 2021: Traded to the Kansas City Royals.
- July 27, 2022: Traded to the New York Yankees.
- January 3, 2023: Signed with the Chicago White Sox as a free agent.
Why the Movement Matters
A lot of people think Benintendi "fell off" because he isn't the superstar he was projected to be in 2017. Honestly, that's a bit unfair. He’s evolved.
He went from a power-hitting rookie to a Gold Glove defender, then to a high-OBP contact hitter, and recently back to someone who can knock 20 out of the park. Teams keep trading for him or signing him because he’s consistent. He’s a "glue" guy.
If you're tracking his career for fantasy baseball or just because you’re a fan, the big takeaway is his resilience. He survived the Boston pressure cooker, found himself in KC, handled the New York media, and became the face of a record-setting deal in Chicago.
For those looking to follow his current performance, keep an eye on his splits against left-handed pitching. In 2024 and 2025, he showed a massive improvement there, which has kept his bat in the lineup even when the White Sox are cycling through younger players. If you're looking for his latest stats or game logs, checking his active status with the White Sox is your best bet, as he's locked into that roster for the foreseeable future.
To get a better sense of his impact, you should look at his defensive runs saved (DRS) during his time in Kansas City versus his current metrics in Chicago. It shows a player who has learned to compensate for aging with better positioning. Following his journey across these four iconic franchises gives you a pretty good map of the modern MLB landscape.