Throughout his career, Strawberry was one of the most feared sluggers in the sport, known for his prodigious home runs and his intimidating presence in the batter's box with his 6 ft 6 in (1.98 m) frame and his long, looping swing that elicited comparisons to Ted Williams.

As an 18-year-old out of Los Angeles’ Crenshaw High School, Strawberry signed a letter of intent with Oklahoma State, to play baseball for Gary Ward.

1985, Strawberry suffered torn ligaments in his thumb, making a diving catch off of Ozzie Virgil of the Philadelphia Phillies.

After starting pitchers Ron Darling of the Mets and John Tudor of the Cardinals dueled scorelessly into extra innings, Strawberry provided the only run of the Mets' 1-0 victory in the 11th inning, hitting a massive home run off of Ken Dayley that hit the clock on the scoreboard in the right field stands of Busch Stadium.

The 1986 Mets jumped to an early lead (a 4-game sweep of the Cardinals in St. Louis was pivotal) and cruised easily to the divisional title, setting a team record with 108 wins.

[10] With the Mets having rallied to take a 6-5 lead in the 8th inning of Game 7, Strawberry hit a home run off of Al Nipper to seal the victory and the series.

He took a notably-slow home run trot around the bases, leading to Nipper throwing at him and igniting a brawl between the teams during spring training, the next season.

In 1987, Strawberry hit 39 home runs and stole 36 bases, joining the exclusive 30–30 club[12] at the time becoming one of only 10 players in baseball history to accomplish the feat.

On Opening Day in 1988, Strawberry hit a massive home run (estimated at 525 ft.) that struck the roof of Olympic Stadium in Montreal.

Strawberry led the Mets to the playoffs, losing to the Dodgers in seven games in the National League Championship Series.

Strawberry signed as a free agent with the Los Angeles Dodgers on November 8, 1990,[10] inking a lucrative five-year $22.25 million contract.

By the end of the 1991 season, he had 280 lifetime homers at the age of only 29, drawing comparisons to then home run king Hank Aaron.

With the Yankees, he showed flashes of his former brilliance, belting 11 home runs in a part-time role and helping his team win the World Series in 1996 alongside former Mets teammates Dwight Gooden and David Cone.

[5] However, he suffered abdominal pain for around two months, which he did not disclose to his teammates or staff, and his playing time declined late in the season.

[19] Strawberry was diagnosed with colon cancer during the American League Division Series (ALDS),[19] and he was replaced on the roster by rookie Ricky Ledée.

[21] Six days after news of the positive test broke, Selig announced that Strawberry would be suspended for the entire 2000 season, effectively ending his career.

The others are his former coach Davey Johnson, who did it as a member of the Philadelphia Phillies, as well as Mike Ivie of the San Francisco Giants, Ben Broussard of the Cleveland Indians, and Brooks Conrad of the Atlanta Braves.

[25] He threw out the ceremonial first pitch at Shea Stadium before Game 1 of the National League Championship Series between the Mets and the St. Louis Cardinals on October 12, 2006.

He served as an anchor on the Mets pre- and post- game shows on SNY in 2007 and 2008, eventually settling into a part-time analysis role for the 2009 season.

In his acceptance speech, Strawberry apologized to Mets fans for leaving to sign with the Dodgers, saying it was "the greatest mistake I ever made".

[36] He attributes his initial alcohol and drug use to the pain he endured as a child and his subsequent substance abuse to the pressures of performing in New York.

[42] On April 3, 1999, Strawberry was arrested in Tampa, Florida for soliciting sex from a policewoman posing as a prostitute and for having a small amount of cocaine.

[49] On March 12, 2002, Strawberry was back in jail for violating several non-drug rules at the drug treatment center where he was on probation in Ocala, Florida.

[52] On or about March 11, 2024, Strawberry suffered a heart attack, underwent a stent procedure and reported that he was recovering in a hospital in Lake St. Louis, Missouri.

In 1988, he was featured heavily in the William Goldman and Mike Lupica book Wait Till Next Year, which looked at life inside the Mets over a whole season (among other New York sports teams).

In 2004, the Rebecca Gilman play The Sweetest Swing in Baseball premiered at the Royal Court Theatre in London.

The lead character ‒ Dana, as portrayed by Gillian Anderson ‒ adopts the personality and speech of Darryl Strawberry in an attempt to pass herself off as schizophrenic.

[citation needed] In 2010, Strawberry appeared on NBC's The Apprentice with Sharon Osbourne, Cyndi Lauper, Bret Michaels, and others.

On February 8, 2011, Strawberry appeared along with Clara Hughes and Stephane Richer on a Canadian documentary by Michael Landsberg to talk about his battle with depression.

[55] On Wednesday, November 15, 2017, Strawberry appeared on The Tonight Show Starring Jimmy Fallon to talk about his new book Don't Give Up on Me, which sheds light on addiction and recovery.