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 methamphetamine distribution. His criminal record includes 33 prior convictions, among them controlled substance violations and a previous federal conviction for conspiracy to distribute methamphetamine.
Gary Winters, 63, was sentenced earlier this year to 25 years in federal prison following his guilty plea last July to conspiracy to distribute a controlled substance and possession with intent to distribute. Gary’s history includes drug trafficking offenses dating back to at least 1999 and a serious drug felony conviction in 2010.
According to evidence presented in the case, both men were involved in an ongoing drug conspiracy between July and August of 2023. During that time, Bradley Winters sold methamphetamine directly to a confidential informant working with law enforcement. Gary Winters was on supervised release for his previous conviction when he participated in the new conspiracy; he was found with over 180 grams of methamphetamine during an August traffic stop.
After being indicted, Bradley Winters was released on pre-trial supervision but failed to appear for court as ordered on July 18, 2024. Authorities discovered he had removed his GPS ankle monitor. An arrest warrant was issued, and officers located him on July 26 in Clear Lake, Iowa. He attempted to flee and resisted arrest while carrying several baggies of methamphetamine and more than $6,000 cash.
Both sentences were handed down by United States District Court Judge Leonard T. Strand in Sioux City—Gary’s on January 3 and Bradley’s most recently—with each brother also receiving a ten-year term of supervised release following their imprisonment. Federal parole is not available.
“Gary Winters and Brad Winters are being held in the United States Marshal’s custody until they can be transported to a federal prison.”
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.
