Jerry Jones on flawed players and Cowboys redemption bets

Jerry Jones has explained the Dallas Cowboys’ long-standing willingness to take chances on troubled talent, citing Charles Haley and the reported 2026 addition of Von Miller as examples of a philosophy he discusses in Netflix’s America’s Team: The Gambler and His Cowboys.

"You’ve even heard it said, ‘You can’t play football successfully with Sunday school teachers.’ So, if you wait around and try to get the player with the perfect character, you’ve given yourself a handicap that’s not necessary. In fact, flawed individuals are some of my greatest role models," Jones said in the documentary.

Charles Haley: the 1992 gamble that delivered three rings

Jones admitted bringing Haley from the San Francisco 49ers was "dicey". Haley arrived with horror stories about scaring coaches, being aggressive and bullying rookies.

Haley himself said in the series: "Let me give you a secret: whatever came into my head, I did. I didn’t give a sh*t." Former teammate Bill Romanowski recalled: "Charles always found a rookie to pick on," and described being targeted as a 49ers rookie, adding a notorious anecdote about Haley confronting management in 1992.

The risk paid off on the field. Haley won three Super Bowls with Dallas after the trade.

Von Miller: modern-day parallel with a troubled past

The article draws parallels between Haley and Von Miller, another two-time Super Bowl winner and edge rusher.

Miller’s controversial past includes a domestic violence case. Court documents obtained by WFAA in November 2023 reported Miller was accused of assaulting his then-pregnant girlfriend at their Dallas high-rise apartment. Police found "minor abrasions" on her hand and bruising on her neck — "injuries consistent with applied pressure to the neck."

According to the arrest warrant affidavit, an argument over travel plans escalated, with Miller allegedly shoving and pushing his girlfriend while filming her, applying pressure around her neck for three to five seconds as she yelled, "Stop! I’m pregnant." The 911 call captured her saying, "My boyfriend is choking and hitting me… I have bruises all over me, my hair is out."

A warrant for a third-degree felony charge of assaulting a pregnant person was issued in November 2023 while Miller played for the Buffalo Bills. He turned himself in, posted a $5,000 bond and was released.

The report states the Cowboys have signed Miller for the 2026 season, raising the question whether Jones’ belief in rehabilitation can produce another Super Bowl run to end Dallas’ 30-year drought.

"Remains to be seen…" the report concludes.