Donald Trump Passed On Purchasing The Dallas Cowboys In 1984, Paving The Path For Jerry Jones To Buy The Team In 1989. What If Trump Had Pulled The Trigger?

You know the real-life stories.

In one corner, there’s Jerry Jones. Self-made billionaire. University of Arkansas alumnus. Three-time Super Bowl Champion. Current owner and general manager of the most valuable franchise in the history of professional sports. A walking soundbite, and the undisputed champion of hype.

In the other, we have Donald J. Trump. Accidental billionaire. Real estate mogul turned political dissident that somehow found himself as president of the most powerful nation in the history of the world. A man embroiled by controversy and personified by a history of reckless (if not downright destructive) decision-making.

Yes, we all know how things have played out professionally and personally both with Jones and with Trump.

But what if things had gone differently, as they almost did back in the ’80s, back when Trump almost purchased America’s Team before Jones ever even got the chance?

This is how that story plays out.

Not-So-Humble Beginnings*

The year is 1984.

Michael Jordan has just launched his rookie campaign with the Chicago Bulls. Ghostbusters is the No. 1 movie in America. Prince and Tina Turner struggle to keep Footloose from taking over the top spot on the Billboard charts.

Jerry Jones, having emerged from his Jimmy Hoffa-funded pizza parlor failures of the late 1960s, negotiates yet another lucrative oil lease from the comfort of his modest, yet functional, Arkansas office. The 41-year-old tycoon is over-leveraged, sure — but he remains confident in his investments.

Halfway across the country, Donald J. Trump sits in a Midtown Manhattan high-rise, basking in his recent successes and plotting his next move. He mulls over his options while working within the luxurious accommodations provided by his latest and greatest real estate venture: Trump Tower.

Trump Tower carries a deep meaning for the 39-year-old commercial real estate guru. Its completion means that he’s finally crawled out from under the shadow of his father and become a success in his own right. Without a doubt, life is good for Donald in 1984. But, as every good businessman will tell you, the work is never finished. Donald’s knows his own outlook is no exception.

It’s here, in this moment, that Donald has an idea — one centering around a fun foray into a world of glitz, glamour, competition and fame.

See, the Dallas Cowboys are for sale — and Donald is giving serious thought to becoming their new owner.


The price tag? A mere $50 million.

That’s chump change for a man of Donald’s financial stature.

He settles on his next play.

*In reality, this is the moment when everything went wrong. Seeing how the Cowboys had set an unachievable bar for success during their first two decades of existence, Trump decided that his money was better suited for a $10 million investment into the USFL’s New Jersey Generals. That decision would prove ill-advised, and his two-year dive into the world of professional sports ended up much like his other, well-documented business failures. That’s to otherwise say this: It couldn’t have gone much worse. Sure, he was able to boast Hall of Famers Herschel Walker and Jim Kelly as part of his Generals squad — but his team never won a playoff game and, in 1986, the league ultimately folded after adopting Trump’s foolish suggestion of moving the USFL season to the fall so as to directly compete with the NFL. But, OK, enough reality for now. Let’s get back to the hypothetical at hand.

A Purchase (And Another Offer)**

The year is 1985.

Donald Trump has just finalized a deal to become the second owner in the history of the Dallas Cowboys. He promptly awards the naming rights of Texas Stadium to his own Trump Organization, thereby rebranding it as Trump Stadium.

In the meantime, the USFL is thriving. Herschel Walker, winner of the 1982 Heisman Trophy winner, has taken the alternative pro football league by the storm. In doing so, the NFL is forced to recognize that Walker’s star power has turned the USFL into a legitimate threat to its market share.

In his third year in the USFL, Walker rushes for a single-season record of 2,411 yards. It’s a professional football rushing record that will remain intact for generations.

Late in the summer of 1985, the checkbooks open up and a decades-long love affair between Donald Trump and Herschel Walker officially begins. Walker leaves behind his life as a New Jersey General, signs an NFL contract to play for the Cowboys and joins his newfound billionaire friend Donald Trump in Dallas.

For his part, Jerry is thriving as an oil tycoon. But as his fortunes mount, an emptiness keeps eating away inside of him. He can no longer deny his burning desire to return to his glory days, when he served as co-captain of the 1964 national champion Arkansas Razorbacks football team. He spends his weeks cutting deals, but his Saturdays are split between watching former teammates — Ken Hatfield at Arkansas and Jimmy Johnson at the University of Miami — carve new identities for themselves as the no-nonsense head coaches of two of the most stories programs in college football.


When Johnson’s success ultimately blossoms into a 1987 national championship in Miami, Jerry sees opportunity back home in Arkansas. Hatfield’s squads may be unmatched in the regular season, but his Hogs just can’t figure out how to translate that success into post-season accolades.

Seeing this and realizing there might be trouble in paradise, Jerry picks up the phone and calls Frank Broyles, his old ball coach and the current athletic director at the University of Arkansas.

“Frank,” Jerry says to Broyles, rather directly. “If you’re ever looking to make a change, I just want you to know I’m available.”

The Dallas Cowboys could use a change at this point themselves. Since Trump took over ownership, his team’s posted a 28-51 record. It’s the end of the 1988 season and, despite the herculean efforts of the walking highlight reel otherwise known as Herschel Walker, the Tom Landry-led Cowboys have entered into the darkest era in the franchise’s history.

Despite pleas from fans, Trump refuses to sell the team. He won’t take such a public loss.

**In reality, this is the time in which Jones swooped in, bought the Cowboys and ultimately turned things around by hiring Jimmy Johnson away from the University of Miami. That move, and the shrewd trades that followed, would result in into three Super Bowl victories over a four-year time period. Alas, there is no white knight for Donald Trump’s Dallas Cowboys.

You’re Fired***

Donald, usually a stickler for tradition, realizes that Tom Landry is no longer the coach he once was. His Cowboys need a change. Anyone can see that.

So, he does what anyone else might do at the time: He reaches out to Miami Dolphins coaching legend Don Shula. Lucky for him, it turns out Shula’s interested.

Meanwhile, across state lines in Arkansas, Broyles is pulling the trigger on a new hire of his own. No, Jerry might not have much coaching experience — but he was on that same 1964 championship team that Johnson was, and Johnsons sure turned out to be a pretty good coach. With Broyles promising to keep a close eye on things, Jerry is announced as the next head coach of the Arkansas Razorbacks.

Back in North Texas, the Cowboys are losing — and not just on the field, but at the bank. Firing Landry and subsequently hiring Shula certainly earned Dallas back some headlines, but the struggles of the late Landry era remain. The team isn’t performing, and the financial losses are stacking up — at a rate of more than $1 million in the red per month.

Simultaneously, it’s becoming increasingly apparent that the USFL still does pose a legitimate threat to the NFL’s dominance. Realizing all of this, Donald Trump reaches out to USFL insiders to put into practice the model put forth in his best-selling 1987 book The Art of the Deal — just behind closed doors, of course.

Instead of looking to trade Walker for a haul of draft picks to use on future franchise fixtures, Trump brokers a deal for the Dallas Cowboys to secede from the NFL and join the ranks of the world’s second-best professional football league.

It doesn’t work out like Trump hopes. The USFL’s Dallas Cowboys continue hemorrhaging money.


Jerry’s doing OK, though! He’s quickly building a college football dynasty in Fayetteville, Arkansas. Come to find out, Jerry has a knack for this coaching thing. It’s his life’s calling. Awards and championships fill the University of Arkansas. Jerry develops into an honest-to-goodness Ozark Mountain hero. Broyles, who hired him, looks like a genius.

Donald, on the other hand, is in a bad way. He doesn’t comprehend what’s happening. The city isn’t supporting his team; his players aren’t winning; his real estate projects are failing. When Walker blows out his knee during his return-to-the USFL season in 1989, it cements what so many already knew: The Dallas Cowboys have fallen from grace.

In a huff, Donald fires Shula and promotes an injured Walker to the title of player-coach. He starts suggesting to his friends at New York City Hall that the Cowboys might fare better in Manhattan. They’re interested — and, in exchange for a taxpayer-funded stadium, Donald agrees to transfer the deed for his beloved Trump Tower back to the city. In exchange, he receives a stable — but comparably modest — licensing and management contract.

The deal actually proves to be something of a success, but only in the short run. Upon a federal investigation spurred by scorned Dallas elites who apparently knew too much, the State of New York indicts Donald on tax fraud charges. Soon as that shoe drops, it’s followed by another: New York City voids its contracts with Donald and rebukes any involvement in his projects.

Federal agents eventually seize control of Trump Tower. Donald doesn’t get his stadium. Instead, he gets an all-expense paid trip to prison.

Only once behind bars does he realizes that The New York City Cowboys will never come to be.

***In reality, 1989 is a pivotal year for the Dallas Cowboys. The team went 1-15 in its debut campaign under new owner Jerry Jones, new coach Jimmy Johnson and new franchise quarterback Troy Aikman. Four games into the season, the Cowboys sent Herschel Walker to the Minnesota Vikings a part of an 18-player, 12-draft pick and three-team transaction that ultimately formed a Cowboys’ core that would go on to hoist three Lombardi trophies over a four-year span. The USFL folded three years earlier due in no small part to the self-appointed advisory role taken on by Trump himself. His football dreams dashed, Trump was focused on his newly acquired properties — the Plaza Hotel in Manhattan and what would become known as the Trump Taj Mahal in Atlantic City. By 1992, both projects would become bankrupt and kick off a domino effect that resulted in Trump losing these assets along with his airline, Trump Shuttle, and his mega-yacht turned high roller hideaway known as the Trump Princess.

A New Dynasty****

The year is 1994.

Jerry has quickly become one of football’s most talented and highly coveted coaching prospects. With all of the success he’s had in Arkansas, pro teams are starting sniffing around, wondering if he’s up for a jump from the NCAA to the big leagues.

Enter Ross Perot Jr.

Hungry to own a professional sports team of his own, Perot has been talking with the NFL behind the scenes. His vision? Bring the Cowboys back to Dallas — and to the NFL. If he can make it all work, he knows just the man to coach the team, too.

The NFL likes what it hears and becomes the first domino to fall. Next, Perot sets his sights on Dallas City Hall, which he successfully lobbies into renovating the decaying Cotton Bowl — not just as the Cowboys’ new home, but as a promised land of economic activity and equitable growth for one of Dallas’ most marginalized neighborhoods.

Those elements in place, Jones agrees to leave his alma mater and join in on Perot’s vision.


Their team-up is something to behold. With Perot managing the business and Jerry handling the action on the field, the Cowboys rattle off three Super Bowl wins in four years — all while restoring glory to South Dallas through a reimagining of Fair Park.

In the year 2000, Jerry finally decides it’s time to step away from the sidelines and agrees to move into a front office role. His first order of business? Hiring his buddy Jimmy Johnson to continue his coaching legacy. Johnson and his hard-nosed coaching style goes leads the Cowboys to another four Super Bowl titles in the ’00s. The Dallas Cowboys are far and away the world’s most valuable — and most successful — professional sports franchise in the world

Donald, having finally served the entirety of his sentence, emerges from his cell a disgraced felon. There is no political career and no reality TV fame; there is only shame.

Occasionally, media outlets will reach out to inquire about an exposé on his fall from grace. Now a small-time landscaper struggling to make ends meet in upstate New York, Donald routinely accepts their offers of wining and dining him.

Unfortunately, his interviews — rambling emotional dumps from a madman who believes the world is still out to get him — never yield anything of value.

Nothing is ever published.

****Rather than the kickoff of a new dynasty for the Dallas Cowboys, 1994 is mostly remembered in real life for the infamous and abrupt divorce between Jones and Johnson. As Texas Stadium began to crumble, a courtship between the Cowboys and the City of Dallas ensued over the possibility of a new stadium. Eventually, though, all talks between the team and then-mayor Laura Miller sputtered. By 2004, it was apparent that the Dallas Cowboys would not be building a new stadium within the Dallas City Limits. Eventually, they settled on a site in the suburb of Arlington. Meanwhile, Donald Trump spent most of the mid-’90s and early 2000s sorting through his failed projects and financial failures of the years prior. Eventually, he pivoted his business efforts away from real estate development and towards licensing opportunities. In 1996, he dove into a world of pageantry beyond the gridiron and signed on as the owner of the Miss Universe, Miss USA and Miss Teen USA beauty pageants.

A Whole New World*****

The year is 2020.

Donald isn’t sure his landscaping business is going to survive the year. He wonders is a Twitter account promoting his company could help.

Jerry can no longer fit all of his Super Bowl rings onto a single hand, and you should see the way he laughs when he tells people that.

Early on in the year, there’s a brief scare surrounding a potential pandemic. The masses are nervous, but a swift government response fueled by science and the studied opinions of experts leads to a quick resolution.

Society bears ahead. America continues spending its Sundays gathered around the television and gleefully consuming the NFL’s as-in-demand-as-ever product.

There is no team in professional sports more adored — or envied — than the Dallas Cowboys. A perennial Super Bowl contender, the franchise is valued at $5.5 billion.


Each weekend, hundreds of thousands of Cowboys fans descend upon the thriving Fair Park entertainment district — if not to catch a game in the Cotton Bowl itself, then to soak up the post-tailgating atmosphere in the many bars showing the game nearby.

Life is good.

It’s really, really good.

*****Life’s actually not that great IRL. Kinda sucks, actually. Really, it can fuck all the way off.

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