MASON CITY, IA – Two brothers from Mason City are facing decades behind bars after being sentenced for running a methamphetamine distribution operation in Cerro Gordo County. Gary Winters, 63, received a 25-year sentence, while his brother, Bradley Winters, 58, was sentenced to 20 years in federal prison. The sentences, handed down by United States District Court Judge Leonard T. Strand, reflect the severity of their crimes and extensive criminal histories.
Federal prosecutors detailed how, between July and August 2023, Gary and Bradley Winters conspired to distribute methamphetamine throughout Mason City. Bradley Winters directly sold drugs to a confidential informant working with law enforcement. Simultaneously, Gary Winters, already on supervised release for a 2010 drug conviction, actively participated in the conspiracy. On August 24, 2023, authorities stopped Gary and discovered he was carrying over 180 grams of methamphetamine.
The situation escalated after Bradley Winters’ indictment. Released on pre-trial supervision, he brazenly skipped a scheduled court appearance on July 18, 2024, in Sioux City. He then cut off his GPS ankle monitor, triggering an arrest warrant. Law enforcement located him in Clear Lake, Iowa, where he attempted a foot chase and physically fought with officers before being apprehended. During the arrest, officers found Bradley in possession of multiple baggies of methamphetamine and over $6,000 in cash.
Gary Winters pleaded guilty on July 24, 2024, to one count of conspiracy to distribute a controlled substance and one count of possession with intent to distribute a controlled substance. His prior record includes a 1999 conviction for possession with intent to distribute methamphetamine and carrying firearms during drug trafficking, as well as the 2010 conviction for conspiracy to distribute 500 grams or more of methamphetamine. He will serve a 10-year term of supervised release after his 300-month prison sentence. Bradley Winters pleaded guilty on March 18, 2025, to two counts of distribution of methamphetamine. He also faces 10 years of supervised release following his 240-month sentence.
The Winters brothers’ criminal histories are extensive. Bradley Winters alone has 33 prior convictions, including a 2009 federal conviction for conspiracy to distribute methamphetamine and distribution of methamphetamine, alongside numerous theft and assault charges. There is no parole in the federal system; both men will serve their full sentences. Currently, Gary Winters and Bradley Winters are in the custody of the United States Marshals awaiting transport to federal prison.
The investigation was a collaborative effort between the Cerro Gordo County Sheriff’s Department, the Clear Lake Police Department, and the Iowa Division of Narcotics Enforcement. Assistant United States Attorney Ron Timmons prosecuted the case. Court file information can be found at https://ecf.iand.uscourts.gov/cgi-bin/login.pl (case file number 23-3032). Follow the United States Attorney’s Office for the Northern District of Iowa on X @USAO_NDIA for updates.
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Key Facts
- State: Iowa
- Agency: DOJ USAO
- Category: Drug Trafficking|Organized Crime
- Source: Official Source ↗
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