Meth-dealing Mason City brothers sent to federal prison for decades

SIOUX CITY – A pair of Mason City brothers were sentenced to more than 20 years in federal prison for methamphetamine distribution.

Bradley Winters (pictured at top), age 58, was sentenced today, to 20 years in federal prison, after a March 18, 2025, guilty plea to two counts of distribution of methamphetamine. Bradley had previously been convicted of a serious drug felony. Bradley’s criminal history is extensive, with 33 prior convictions. His convictions include controlled substance violations (including a 2009 federal conviction for conspiracy to distribute methamphetamine and distribution of methamphetamine), multiple thefts, and multiple assaults.

Gary Winters, age 63, was sentenced January 3, 2025, to 25 years in federal prison, after a July 24, 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 had previously been convicted of a serious drug felony in 2010. Gary’s criminal history includes a 1999 possession with intent to distribute methamphetamine and carrying firearms in connection with drug trafficking and a 2010 conviction for conspiracy to distribute 500 grams or more of methamphetamine.

Evidence in the case revealed that between July 2023 and August 2023, Bradley Winters and Gary Winters were part of an ongoing drug conspiracy based in Mason City, Iowa to distribute methamphetamine. Bradley Winters sold methamphetamine to a confidential informant, working with law enforcement. Gary was serving a term of supervised release for his 2010 drug conviction when he was involved in the conspiracy, including his possession of over 180 grams of methamphetamine when he was stopped by law enforcement on August 24, 2023.

After Bradley was indicted in this case, he was released on pre-trial supervision. Bradley failed to appear as ordered on July 18, 2024, in federal court in Sioux City. It was later discovered that Bradley cut off his GPS ankle monitor. An arrest warrant was issued for his arrest, and on July 26, 2024, Bradley was located by officers in Clear Lake, Iowa where he fled from officers on foot and fought with them. Bradley was in possession of several baggies of methamphetamine, as well as more than $6,000 cash.

Gary Winters was sentenced on January 3, 2025, in Sioux City by United States District Court Judge Leonard T. Strand to 300 months’ imprisonment. He must also serve a 10-year term of supervised release after the prison term. Bradley Winters was sentenced today, by United States District Court Judge Leonard T. Strand to 240 months’ imprisonment. He must also serve a 10-year term of supervised release after the prison term. There is no parole in the federal system.

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 case was investigated Cerro Gordo County Sheriff’s Department, Clear Lake Police Department, and the Iowa Division of Narcotics Enforcement, and was prosecuted by Assistant United States Attorney Ron Timmons.