Timothy T. Duax U.S. Attorney | U.S. Attorney for the Northern District of Iowa
Two brothers from Mason City, Iowa, have been sentenced to lengthy federal prison terms for their roles in distributing methamphetamine. Bradley Winters, 58, received a 20-year sentence after pleading guilty in March 2025 to two counts of distribution of methamphetamine. According to court records, Bradley Winters has a criminal history that includes 33 prior convictions such as controlled substance violations—including a 2009 federal conviction for conspiracy to distribute and distribution of methamphetamine—multiple thefts, and assaults.
Gary Winters, 63, was sentenced earlier this year on January 3 to 25 years in federal prison following his July 2024 guilty plea to one count of conspiracy to distribute a controlled substance and one count of possession with intent to distribute a controlled substance. Gary also had previous serious drug felony convictions dating back to at least 1999 and was convicted in 2010 for conspiracy to distribute more than 500 grams of methamphetamine while carrying firearms.
Evidence presented in the case showed that between July and August of 2023, both brothers were involved in an ongoing drug conspiracy based in Mason City. During this period, Bradley Winters sold methamphetamine directly to a confidential informant working with law enforcement. At the time, Gary Winters was serving supervised release for his prior conviction but still participated in the conspiracy; he was found with over 180 grams of methamphetamine during an August traffic stop by law enforcement.
After being indicted, Bradley Winters was released on pre-trial supervision but failed to appear as ordered on July 18, 2024. Authorities later discovered he had removed his GPS ankle monitor. An arrest warrant was issued and on July 26, officers located him in Clear Lake where he attempted to flee and resisted arrest. He was found carrying several baggies containing methamphetamine and more than $6,000 cash.
Both men were sentenced by United States District Court Judge Leonard T. Strand—Gary receiving a sentence of 300 months (25 years) plus a ten-year term of supervised release; Bradley receiving a sentence of 240 months (20 years) plus ten years’ supervised release after incarceration. Federal sentences do not allow parole.
Currently, both Gary and Bradley Winters are held by the United States Marshal’s Service pending transfer to federal prison facilities.
The investigation involved 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.
