The Legal Troubles That Sent Former Quarterback Ryan Leaf to Jail After the NFL

Content warning: This article mentions substance abuse.

In 1998, Ryan Leaf was selected by the San Diego Chargers — now known as the Los Angeles Chargers — as the second overall pick in that year's NFL Draft. Despite high expectations, his professional career was cut short due to poor performance, behavioral issues, injuries, and difficulty maintaining focus and work ethic.

Just four years later, his NFL career came to an end. Ryan went on to finish his degree at Washington State, but his post-NFL life was marked by a series of legal troubles that ultimately led to time behind bars. Here's everything you need to know, including why he actually went to jail.

After retiring from football, Ryan Leaf returned to Montana and quickly fell into substance addiction. He told USA Today Sports in 2017 that his addiction began with painkillers prescribed after surgeries during his NFL career but escalated after retirement in 2002.

A night in Las Vegas, where he was offered Vicodin, marked the start of an eight-year struggle with opioid abuse: "I was uninhibited," he explained. "And I didn't have to feel anything — the failure, the pain, the anxiety, the depression, all of it."

In May 2009, Leaf's legal troubles peaked when he was indicted in Texas on burglary and drug charges. Nearly a year later, in April 2010, he pleaded guilty in Texas to eight felony drug charges. He was sentenced to 10 years' probation and fined $20,000.

In 2012, Leaf was arrested twice within four days in Montana on burglary and drug charges. He took a plea deal, admitting to felony burglary and drug possession. Texas authorities then issued new arrest warrants with a $126,000 bond.

On June 19, he was sentenced to seven years in custody of the Montana Department of Corrections, beginning with treatment at a rehab facility.

However, he was moved to Montana State Prison in January 2013 for violating treatment rules. Leaf was later incarcerated at Crossroads Correctional Facility.

A little over two years later, in September 2014, a Texas judge sentenced him to five years but credited his time served in Montana. Leaf was released in December 2014 and placed under probation supervision.

On May 22, 2020, Leaf was arrested again, this time for misdemeanor domestic battery in California. He later took a plea deal, receiving three years' probation and a year-long domestic violence class.

In July 2024, Ryan Leaf returned to Montana State Prison — not as an inmate, but as a guest speaker. He shared his story with those currently incarcerated, many of whom are battling the same cycles of addiction he once faced.

"I think it helps for me to step into that room and tell them that I relate and can identify with them probably better than anybody out in the public," he told Montana Sports at the time. "That I was exactly where they were 10 years ago. And you can have the life of your dreams. You just have to do the next right thing."

A central theme of Leaf's inspirational message was the idea that no one should be defined by the worst thing they've done — something that clearly struck a chord with the audience.