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Life as an NFL owner seems like a pretty sweet gig. It means you’re pretty wealthy—that’s a necessity to buy the team, and then you’ll almost always turn a profit—and includes plenty of perks like luxury suites, making personnel decisions, and heading to the Super Bowl each winter. Ownership isn’t all fun and games, though. Just Jerry Jones about his time at the helm of the Dallas Cowboys.

Although Jones has turned a massive profit owning America’ Team, there have been plenty of tough moments in Dallas. In fact, several losses reduced the owner to tears.

Jerry Jones’ road to owning the Dallas Cowboys

When you think of Jerry Jones, you’ll probably automatically picture him watching his beloved Dallas Cowboys. The owner’s love of football, however, started long before he became a billionaire.

Jones played football in high school and continued his athletic career at the University of Arkansas. Despite being tiny by today’s standards, he found a home on the Razorbacks’ offensive line; he served as one of the team’s co-captains and helped capture a national championship in 1964.

After his college career came to an end, Jones tried to find a new niche away from the gridiron. He took a crack at entrepreneurship but fell promptly flat; his Shakey’s Pizza franchises went bust and his attempt at buying the San Diego Chargers came up short. Those setbacks, however, wouldn’t break Jones’ will.

After spending some time as an executive vice president of Modern Security Life Insurance, which was his father’s company, Jerry decided to strike out on his own. Soon after founding Jones Oil and Land Lease, he stuck black gold; that wealth, in turn, helped him buy the Dallas Cowboys.

Suffering three tear-jerking losses

During his time with the Dallas Cowboys, Jerry Jones has had some incredible highs and some brutal lows. While nothing can take away his three Super Bowl titles, the owner has been reduced to tears by three specific losses.

As Jones explained to the Dallas Morning News in 2014, the first defeat came at the height of the Cowboys’ power. In January 1995, however, their chance at a threepeat was crushed in the NFC title game. “I couldn’t hold it in there in San Francisco that day,’’ Jones explained, looking back at the 38-28 loss to the 49ers. “I knew we had the better team.’’

Jones’ next emotional moment came at the start of the 2002 campaign when the Cowboys lost to the Houston Texans in the new franchise’s first regular-season game. “I was the leading proponent of getting Houston the team. I wanted those fans to have their own team, even though I knew at that time half of them were Cowboys fans,” he explained. “To go down and get beat on opening night by an expansion team was absolutely a low point.’’

The final time Jones was reduced to tears was after his Cowboys were upset in the NFC Divisional Round by the rival New York Giants; a 13-3 regular season proved to be for naught. “That’s where I went to the place I used to go to when they would call and tell me that I had just lost all of my money on a dry hole,’’ Jones remembered.

It’s worth noting that Jones did appear emotional after the Cowboys lost to the Buffalo Bills on Thanksgiving 2019. It’s unclear, however, if being teary-eyed counts as crying.

Tears or not, owning the Cowboys has paid off for Jerry Jones

Despite those painful losses and at least one other regret, it’s safe to assume that Jerry Jones doesn’t regret buying the Dallas Cowboys. Beyond attaining his dream of owning an NFL franchise, the team has helped him turn a massive profit.

When Jones bought the Cowboys in 1989, he spent $140 million on a floundering franchise. While the team might have fallen from their dominance during the 1990s, they’re still a financial juggernaut. The Dallas Cowboys are now valued at estimated $5 billion and Jones himself has an approximate net worth of $8.5 billion.

Losses are never fun, especially when you’re the owner of the team. Jerry Jones, however, probably doesn’t have a problem trading a few tears for $8.5 billion and three Super Bowl titles.