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Why Did Darryl Strawberry Go To Prison?

Darryl Strawberry is a former Major League Baseball right fielder who played for the New York Mets, Los Angeles Dodgers, San Francisco Giants, and New York Yankees. Strawberry was one of the most feared sluggers in baseball during the 1980s and 1990s and was named to 8 straight All-Star teams from 1984-1991. However, off the field issues including battles with substance abuse and legal troubles derailed what could have been an even greater career. Strawberry’s problems with the law eventually led to multiple stints in prison during the 2000s.

Darryl Strawberry’s Early Career

Darryl Strawberry was born in Los Angeles, California in 1962. He was selected by the New York Mets with the 1st overall pick in the 1980 MLB Draft after a standout high school career. Strawberry made his MLB debut in 1983 at the age of 21 and immediately became one of the top power hitters in the game. In his rookie season, Strawberry hit 26 home runs and was named the National League Rookie of the Year.

Over the next 8 seasons with the Mets, Strawberry hit 252 home runs and led the league twice in long balls. He was also instrumental in helping the Mets win the 1986 World Series, their last championship to date. Besides his prodigious power, Strawberry became known for his intimidating presence in the batter’s box with his 6’6″ frame and picture perfect swing. It seemed like superstardom was within reach.

Darryl Strawberry’s Legal Issues Begin

However, Strawberry’s career soon started to unravel due to off-the-field problems. In 1987, Strawberry checked into an alcohol rehab facility for the first time before the start of the season. In 1990, Strawberry was arrested for allegedly hitting his wife and threatening her with a gun during a domestic dispute. The charges were later dropped. After more legal issues and declining performance, the Mets opted not to re-sign Strawberry when he became a free agent after the 1990 season.

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Strawberry signed with the Los Angeles Dodgers in 1991 and seemed to regain his form, hitting 28 home runs and being named Comeback Player of the Year. But more drug and legal issues caused him to miss significant time in 1992 and 1993. The Dodgers let him go after the 1993 season, leading to short and unproductive stints with the Giants and Yankees.

Strawberry’s Downward Spiral Leads to Prison

By the late 1990s, heavy cocaine use had derailed Darryl Strawberry’s once-promising career. He was suspended by MLB repeatedly for cocaine abuse. His legal problems mounted during this period as well:

  • In 1994, he was arrested for failing to pay over $100,000 in child support.
  • In 1995, he was charged with tax evasion.
  • In 1999, he was convicted of soliciting sex from an undercover police officer and sentenced to probation and community service.

The 1999 conviction was the last straw for MLB, who suspended Strawberry for one year for violating the league’s drug policy. After the suspension ended, Strawberry attempted a brief comeback but could not stay out of trouble.

Tax Evasion Conviction and Prison

In 2000, the IRS caught up with Strawberry, charging him for filing false tax returns from 1989-1990. He was alleged to have not reported over $500,000 in income. In January 2001, Strawberry pleaded guilty to tax evasion and was sentenced to 6 months home confinement and probation.

However, just a few months later in April 2001, Strawberry violated his probation by driving under the influence and fleeing the scene of an accident. As a result, his probation was revoked and he was sentenced to 11 months in prison.

After being released in 2002, Strawberry again tried to make a baseball comeback but was suspended indefinitely by MLB after testing positive for cocaine. His drug addiction persisted despite more stints in rehab.

Drug Charges and More Prison Time

In 2004, Strawberry was once again arrested for possession of cocaine and soliciting the services of a prostitute. A year later in 2005, Strawberry admitted to violating his probation by leaving a drug treatment center. He was sentenced to more prison time as a result.

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In 2006, Strawberry was arrested yet again for violating probation by using drugs and not reporting to his probation officer. This led to even more jail time.

By early 2009, Strawberry had been suspended by MLB five times and served multiple prison terms related to drugs, solicitation, and probation violations. His successful playing career had given way to a tragic cycle of substance abuse and run-ins with the law. Baseball and Darryl Strawberry seemed like a distant memory.

Darryl Strawberry’s Road to Redemption

Amazingly, after reaching rock bottom, Darryl Strawberry slowly began to turn his life around. In 2009, a judge sentenced him to probation rather than prison, allowing him to voluntarily enter a drug treatment program.

Strawberry completed the program and finally got sober, later citing his deep religious faith as crucial in defeating his demons. He also made amends with his ex-wife and children.

In recent years, Strawberry has focused on helping others, becoming a mentor and substance abuse counselor. He offers advice to young players about avoiding his mistakes. While drugs derailed his career, Strawberry is working to put his life back together and use his experiences to help the next generation of baseball stars.

Why Did Darryl Strawberry Go to Prison: A Summary

In summary, here are the key reasons why Darryl Strawberry served multiple stints in prison during the 2000s:

  • Repeated cocaine abuse and refusal to get sober
  • Tax evasion conviction in 2001 led to 6 months home confinement and probation
  • Violated probation by drunk driving in 2001, leading to 11 months in prison
  • 2004 arrest for cocaine possession and solicitation led to more prison time
  • 2005 probation violation brought more jail time
  • 2006 arrest for using drugs and not meeting probation officer led to more imprisonment

Strawberry repeatedly broke the law related to drugs, solicitation, probation violations, and tax evasion. Rather than take advantage of second chances like MLB suspensions and probation, he continued to use drugs and break the rules of his probation. As a result, the legal system had little choice but to send Strawberry to prison on multiple occasions.

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Thankfully, Strawberry eventually got sober starting in 2009 and has turned his life around. He now uses his experiences to help others avoid the pitfalls that sent him to prison repeatedly during the 2000s.

What crimes did Darryl Strawberry commit?

The main crimes that led to Darryl Strawberry’s imprisonment were:

  • Tax evasion
  • Drug possession (cocaine)
  • Solicitation of prostitution
  • Probation violations including driving under the influence

How many times was Darryl Strawberry arrested?

In total, Strawberry was arrested at least 5 times for various crimes including drug possession, solicitation, and probation violations between 1994 and 2006. Each arrest ultimately led to more jail time.

How much prison time did Strawberry serve?

Though sentences were sometimes concurrent, in total Strawberry likely served nearly 3 years in prison through his various stints between 2001-2006. His longest single sentence was 11 months in 2001.

Could Strawberry have avoided prison time?

Yes, if Strawberry had taken advantage of the many second chances he was given, like entering drug rehab in the 1990s and abiding by probation terms, he could have avoided prison time. However, his cocaine addiction proved extremely difficult to overcome.

Where was Strawberry imprisoned?

Records indicate Strawberry served time at the Hillsborough County Jail in Tampa, Florida; South Bay Correctional Facility in Florida City, Florida; and Tri-County Correctional Facility in Mechanicsburg, Pennsylvania.


Darryl Strawberry’s recurring legal troubles and inability to stop using cocaine derailed a baseball career that could have led to the Hall of Fame. Multiple arrests and probation violations related to drugs, solicitation, and tax evasion resulted in nearly 3 cumulative years in prison between 2001-2006 for the troubled slugger. Had Strawberry been able to get sober earlier and comply with the law, he may have avoided doing hard time. Thankfully, starting in 2009, Strawberry was finally able to beat his addiction and turn his life around through faith and helping others. Though drugs sent Strawberry to prison repeatedly, he now serves as a cautionary tale about squandered potential and the importance of seeking help when battling addiction.

Prison Inside Team

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Welcome to ‘Prison Inside,’ a blog dedicated to shedding light on the often hidden and misunderstood world within correctional facilities. Through firsthand accounts, personal narratives, and insightful reflections, we delve into the lives of those who find themselves behind bars, offering a unique perspective on the challenges, triumphs, and transformations that unfold within the confines of these walls.

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