Darryl Strawberry has been jailed for a couple of different legal issues in his past, though the contexts and outcomes differ across sources.
- In the early 2000s, he received prison time related to probation violations tied to prior drug-related offenses. He was sentenced to 18 months in prison in Florida after violating probation stemming from a 1999 conviction on drug and solicitation of prostitution charges. This is the incident most commonly cited in mainstream reporting about his time in jail. [news source summaries and archival reports indicate the 18-month sentence]
- Separately, a 1995 tax-related case led to a felony conviction for failing to report income from autograph signings and other memorabilia activities. He later received clemency in 2025 from the president regarding that tax evasion charge. While clemency did occur, the underlying tax-related conviction is distinct from the later probation violation case. [news reports and official statements from 2025 discuss the pardon]
If you’d like, I can pull up the exact articles or court records for these events to give precise dates and docket numbers.
