Hawkeye Reporter

Two Mason City brothers have been sentenced to lengthy federal prison terms for their roles in a methamphetamine distribution conspiracy. Bradley Winters, 58, received a 20-year sentence after pleading guilty in March 2025 to two counts of distributing methamphetamine. Gary Winters, 63, was sentenced in January 2025 to 25 years following his guilty plea on charges of conspiracy to distribute and possession with intent to distribute a controlled substance.

Both men have significant criminal histories involving drug offenses and other crimes. Bradley Winters has 33 prior convictions, including previous federal drug convictions from 2009 related to methamphetamine. Gary Winters was previously convicted in 2010 for conspiracy to distribute methamphetamine and had also been convicted in 1999 for possession with intent to distribute methamphetamine while carrying firearms during drug trafficking.

According to evidence presented in the case, between July and August of 2023, the Winters brothers were involved in an ongoing drug conspiracy centered in Mason City, Iowa. During this period, Bradley sold methamphetamine to a confidential informant working with law enforcement. At the time of his involvement, Gary was serving supervised release from his earlier conviction when he was found possessing 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 at a scheduled court hearing on July 18, 2024. Authorities later discovered that he had removed his GPS ankle monitor. An arrest warrant was issued; on July 26, officers located him in Clear Lake, Iowa where he attempted to flee and fought with law enforcement officers. He was found carrying several baggies of methamphetamine and more than $6,000 cash.

Gary Winters received his sentence from United States District Court Judge Leonard T. Strand: "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." Similarly: "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 available under the federal system.

Both men are currently held by the United States Marshal’s Service pending transfer to federal prison facilities.

The investigation involved multiple agencies including 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.