GRIMY TIMES EXCLUSIVE: Mason City, Iowa – The Winters brothers, Bradley, 58, and Gary, 63, have been handed down prison sentences of more than 20 years for their roles in a methamphetamine distribution conspiracy. Bradley Winters was sentenced to 240 months in federal prison today after pleading guilty on March 18, 2025, to two counts of distribution of methamphetamine. His record is marred by 33 prior convictions, including serious drug felonies and violent crimes.
Gary Winters, previously convicted of a serious drug felony, received a sentence of 300 months’ imprisonment after pleading guilty on July 24, 2024, to conspiracy to distribute a controlled substance and possession with intent to distribute. His sentence includes a mandatory 10-year term of supervised release following his prison term.
Between July and August 2023, the Winters brothers were part of an ongoing drug conspiracy in Mason City, selling methamphetamine to law enforcement informants. Gary was serving supervised release for a previous drug conviction when he was caught with over 180 grams of meth during an August 2023 traffic stop.
Bradley Winters’ sentence was delayed by his attempt to flee from authorities on July 26, 2024. He cut off his GPS ankle monitor and fought with officers, who found him in possession of methamphetamine and cash. He faced charges for failing to appear in court and evading law enforcement.
The investigation into the Winters brothers was a collaborative effort between the Cerro Gordo County Sheriff’s Department, Clear Lake Police Department, and the Iowa Division of Narcotics Enforcement. Assistant United States Attorney Ron Timmons prosecuted the case.
Both defendants are currently in custody of the United States Marshal’s Service and will be transported to federal prisons to serve their sentences. The court file for this case is available at https://ecf.iand.uscourts.gov/cgi-bin/login.pl, Case Number 23-3032.
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Key Facts
- State: Iowa
- Agency: DOJ USAO
- Category: Drug Trafficking|Fraud & Financial Crimes|Violent Crime
- Source: Official Source ↗
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