America’s Team: A Gambler and His Cowboys dives into the Dallas dynasty of the early 1990s, but with fresh honesty. Jerry Jones recounts a debt-laden start that exceeded 15 million dollars, followed by a blockbuster oil strike that funded a half-century of Cowboys ambition. The doc shows the team bleeding cash at times, including reports of losing around a million per month in the earliest ownership days, reframing the risk-taking that defined the era.

Michael Irvin and Jimmy Johnson emerge as the heartbeat of a roster transformation, with Irvin recalling a pre-draft heads-up about a possible buyer and a self-described power shift once Johnson took the reins. Aikman contemplates a trade during the 1991-92 season, revealing how star players contested control and sought moves that could alter franchise fortunes. Bonding moments—like Johnson helping Aikman set up aquariums—become surprisingly intimate keys to the Cowboys’ chemistry and on-field success.

Memorable clashes surface too: Charles Haley’s helmet-throwing tirade in the Emmitt Smith negotiations, Aikman’s friction with Switzer, and Irvin’s high-profile cocaine trial—all painting a behind-the-scenes drama that adds texture to the legacy. The series also touches on a near-bid for the Chargers with Hoffa’s backing, underscoring how the dream of owning a team nearly collided with risky, real-world forces. The Cowboys’ ride through that era is recast as a blend of swagger, calculated risk, and undeniable talent.