Documentary: Cowboys Owner Jerry Jones Asked Jimmy Hoffa For Loan to Buy Chargers

While the Dallas Cowboys might be staring down a pretty brutal season in 2025 with uncertainty almost everywhere on the field, one thing we can’t avoid is the objective awesomeness of a brand new Netflix documentary: “America’s Team: The Gambler and His Cowboys” which dropped all 8 episodes on August 19.

One of the crazier revelations from the documentary, directed by brothers Chapman and Maclain Way, was that Cowboys owner Jerry Jones almost bought the San Diego Chargers in 1966 after a meeting with Teamsters boss Jimmy Hoffa — one of the most notorious figures in American history and someone who was well known to have deep ties to organized crime.

In order to buy the Chargers, Jones would have had to take out a loan from the Teamsters. He’d previously borrowed money from Hoffa and the Teamsters to buy a string of Shakey’s Pizza franchises.

“I met with Hoffa and he told me that (the Teamsters) thought for awhile they could get into professional football,” Jones said in Episode 2. “So I went to my father and told him what was going on and he said ‘This is insane, what happens when you can’t pay?’ ”

That bit of advice from his father caused Jones to back off and the Chargers were eventually sold to businessman Gene Klein, who would own the team until 1984 and was also one of the founding owners of the NBA’s Seattle SuperSonics — now the reigning NBA champion Oklahoma City Thunder.

Hoffa One Of America’s Most Infamous Figures

Hoffa’s disappearance in 1975 remains one of the most intriguing unsolved mysteries in American history.

The president of the International Teamsters Union from 1957 to 1971, Hoffa’s ties to the mafia and organized crime only added to his power as he oversaw a union that claimed over 1 million members until he was convicted on charges of jury tampering, attempted bribery, conspiracy, mail fraud and wire fraud in 1964 and eventually sentenced to 13 years in prison in 1967.

U.S. President Richard Nixon commuted Hoffa’s sentence in 1971 with the condition he could not participate in union activities until 1980.

After Hoffa unsuccessfully tried to regain control of the Teamsters in 1975, he disappeared and was eventually declared dead in 1982 — thought to have been murdered as part of a mafia hit although the circumstances of his disappearance and/or death still remain a source of fascination to the general public.

Jones Eventually Made ‘Deal of the Century’

The Netflix documentary isn’t the first place the Hoffa story has been told by Jones — he told HBO’s “Real Sports” in 2015 — but the key is he eventually did buy an NFL team when he purchased the Cowboys from Bum Bright for $140 million in February 1989 with money mostly made off of oil and gas speculation in Northern California.

Jones’ purchase of the Cowboys represents probably the greatest deal in the history of professional sports. As of 2025, the Cowboys were valued at $12 billion, making them the most valuable professional sports franchise in the world.

“Very early on, the club was losing (money),” Jones told ESPN’s Adam Schefter in 2017. “The Cowboys, that I bought — this is not going to make many people respect me as a businessperson — but I bought the Cowboys and they were losing $1 million cash a month, $1 million a month.”