You know, there’s this old, dusty quote from 1984 that basically explains why the NFL looks the way it does today. Donald Trump was looking at buying the Dallas Cowboys for about $50 million. He famously passed, saying he felt "sorry for the poor guy" who would eventually buy the team because it was a "no-win situation."
Well, that "poor guy" ended up being Jerry Jones. He bought the Cowboys in 1989 for $140 million. Today, they’re worth roughly $12.8 billion.
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Honestly, the relationship between Jerry Jones and Donald Trump is one of the weirdest, longest-running soap operas in American business and sports. It’s not just about two rich guys who like cameras. It’s a decades-long saga of missed opportunities, political tug-of-wars, and a shared obsession with being the center of attention.
That $12 Billion "No-Win" Situation
If you’ve ever wondered why the USFL isn’t a household name, you can thank the rivalry—or perhaps the diverging paths—of these two. Back in the mid-80s, Trump chose the New Jersey Generals of the USFL over the Cowboys because he thought the NFL was moving "laterally." He wanted to force a merger by moving the USFL to the fall to compete directly with the NFL.
It backfired. Spectacularly.
The USFL won an antitrust lawsuit against the NFL but was famously awarded only $3.00 in damages. Jerry Jones, meanwhile, didn't try to fight the system from the outside. He bought the Cowboys, fired Tom Landry, and basically invented the modern sports-marketing machine.
When Politics Collided with the Gridiron
Fast forward to the late 2010s. Things got kinda messy. Most people remember the national anthem controversy, but the friction between Jerry Jones and Donald Trump during this period was surprisingly nuanced.
Trump was publicly hammering the NFL, telling owners they should fire players who kneeled. At first, Jerry seemed to be in lockstep. He was one of the first owners to demand his players "toe the line" and stand for the anthem. Trump even tweeted, "Jerry is a winner who knows how to get things done."
But then the tone shifted.
By July 2018, Jerry was calling Trump’s involvement in the anthem debate "problematic." He basically told the president to stay in his lane. Why? Because Jerry is a businessman first. When the President of the United States starts hurting the NFL brand, Jerry’s loyalty to the league's bottom line is going to beat out his personal friendship every single time.
The 2026 "Venezuela" Moment
Even now, in early 2026, these two are still linked in the most random ways. Just a few days ago, Jerry Jones was holding an end-of-season press conference after a rough 7-9-1 year. The Cowboys had just fired defensive coordinator Matt Eberflus.
When a reporter asked Jerry if head coach Brian Schottenheimer would have the final say on the next hire, Jerry dropped a bizarre joke: "Trump just said it. I’m running Venezuela."
The room laughed, but it was a classic Jerry move. He uses Trump’s rhetorical style and recent news cycles to remind everyone that, at the end of the day, he is the one in charge of the Dallas Cowboys. It was a subtle nod to the idea of total executive control—a trait both men share to their core.
The Business Reality of the Jones-Trump Dynamic
Look, they’re friends. Or at least, they’re peers who respect the hustle. Jerry has donated to Republican causes—like $20,000 to Ted Cruz recently—but he’s rarely a loud-and-proud political operative. He’s too busy trying to chase Robert Kraft’s six Super Bowl rings.
Here is what most people get wrong about their relationship:
- It isn't a partnership: They are competitors for the same cultural "airtime."
- It isn't purely political: Jerry has admitted that Trump’s anti-DEI stances made the league "aware," but he also credited Supreme Court rulings for changes in how the NFL handles diversity programs.
- It's about the "What If": Every time the Cowboys' valuation hits a new record, it serves as a reminder of Trump's biggest business blunder.
What You Can Actually Learn From This
If you’re looking at this from a business or leadership perspective, the Jerry Jones and Donald Trump story offers a few cold, hard truths.
- Timing is everything. Trump wanted the "new" thing (USFL) and missed the "established" thing (NFL) at its lowest valuation.
- Protect the brand above all. Jerry sided with the league's stability over the President's rhetoric when the money was at stake.
- Keep them talking. Both men understand that being "boring" is the only true sin in modern American media.
If you want to track where this goes next, keep a close eye on the 2026 NFL spring meetings. With the Cowboys looking to "bust the budget" to fix their defense, Jerry’s willingness to navigate political waters while keeping his checkbook open will likely define the final chapter of his ownership.
Actionable Next Steps
- Watch the Valuation: Check the next Forbes NFL valuation report to see if the Cowboys cross the $13 billion mark; it's the ultimate scoreboard for Jerry's 1989 bet.
- Monitor the Coaching Search: Follow the Cowboys' defensive coordinator hunt to see if Jerry actually yields control to Schottenheimer or keeps "running Venezuela" himself.
- Track Policy Shifts: Keep an eye on the NFL's "accelerator" programs for minority coaches, as Jerry’s recent comments suggest the league is recalibrating its approach based on the current political and legal climate.