The Long Strange History of Cabo and the Dallas Cowboys

Ezekiel Elliott’s recent contract holdout has put the words “Cabo” and “Cowboys” together in a lot of news stories, causing considerable worry not only to millions of fans of the iconic Dallas based National Football League franchise, but even greater numbers of fantasy football players.

What casual fans may not know is that this isn’t the first time the two words–Cabo and Cowboys–have shared headline space. It’s not even the first time “Zeke” has retreated to Cabo San Lucas to work on his “training” regimen.

Truth is, “America’s Team” and everyone’s favorite Land’s End travel destination have crossed paths many times during the past 30 years…sometimes more memorably than others.

For the uninitiated, here’s a brief history lesson.

Dallas Cowboys owner Jerry Jones has a long history with Cabo San Lucas. Photo credit: Keith Allison.

Jerry Jones Cuts Cabo Vacation Short to Buy the Cowboys

The modern history of the Dallas Cowboys actually begins in Cabo San Lucas, star travel attraction of the Los Cabos municipality which hugs the southernmost rim of the Baja California peninsula. That’s where Jerry Jones was vacationing with family when he confirmed rumors that then Cowboys owner H.R. “Bum” Bright was finally willing to sell the team.

Jones immediately flew back from Cabo to pursue the opportunity, and the rest is sports history. He officially purchased the Dallas Cowboys from Bright on February 25, 1989, paying the then princely sum of $140 million for the privilege.

Although his ownership reign got off to a rocky start with the firing of legendary long-time coach Tom Landry, things improved dramatically after Jones hired Jimmy Johnson, a former college teammate on the University of Arkansas football team, to take over head coaching duties. The Cowboys won back-to-back Super Bowls following the 1992 and 1993 seasons before egos clashed and Johnson was sent packing.

Former Oklahoma head ball coach and bootlegger’s son Barry Switzer then assumed the sideline leadership role for the Cowboys, the core of which remained intact from Johnson’s tenure, and led the team to yet another title after a 12-4 season in 1995.

That adds up to three Super Bowl wins during the Jerry Jones era, suggesting the former oil and gas magnate made a wise decision when he cut that long-ago Cabo vacation short. There’s also the fact, of course, that the team’s valuation now exceeds five billion dollars, making the Cowboys the most valuable property in all of professional sports.

In 2019, Jones celebrated the 30-year anniversary of the purchase by buying a yacht for more money than he originally paid for the Cowboys back in 1989. What better way to get back to Cabo?

Sports fans don’t like it when the hometown quartback takes a vacation before a big playoff game, as Tony Romo found out the hard way. Photo credit: Bigcats lair.

Tony Romo Takes an Ill-Timed Vacation

There’s nothing unusual about Tony Romo visiting México. After all, the former Dallas Cowboys quarterback and current CBS broadcaster has Mexican heritage. His birth certificate reads Antonio Ramiro Romo, the Ramiro name given in honor of his paternal grandfather, who emigrated from Múzquiz, Coahuila to San Antonio, Texas a few generations back. But timing is everything in life and Romo took one of the most ill-timed vacations in NFL history, traveling to Cabo San Lucas in January 2008, the week before a playoff matchup against the team’s hated rival, the New York Giants.

“You don’t go to Cabo the week before a playoff game,” former Dallas Cowboys quarterback and three-time Super Bowl champion Troy Aikman was quoted as saying at the time. “You just don’t do it.”

Romo didn’t heed this advice and in fact compounded his error by taking his then girlfriend, who just happened to be the famous actress and singer Jessica Simpson, a woman pop star John Mayer would later describe in a Playboy interview as “sexual napalm.” Alert paparazzi snapped photos of the pair poolside in swimsuits, and another caught them making out in the backseat of a car like teenagers.

Taking a romantic getaway vacation at such an important time of year for the Cowboys predictably set off a public relations firestorm, with fans not at all happy about their quarterback’s questionable decision making. Many held up mocking or castigating signs at the divisional round playoff game against the Giants, which the Cowboys of course lost by a score of 21-17. A Dallas area car dealership even warned Simpson via a sign out front to “keep away from Tony.”

The warning didn’t work. Romo was thoroughly outplayed by his opposite number, Eli Manning, whose quarterback rating was more than double Romo’s anemic 64.7. Manning’s Giants then continued on to the Super Bowl, where they beat the previously undefeated New England Patriots in one of the most memorable title games of all-time.

Romo, meanwhile, continued to take heat for his Cabo vacation. In an attempt to defend himself after the game he gave an impassioned plea for Cabo as a much better rest and recreation locale than his other choice, Las Vegas, where he said there was nothing to do but drink “for two or three days.” The defense fell on deaf ears.

Although a very good quarterback during his 13-year Cowboys tenure, Romo is now remembered as a player primarily for his playoff shortcomings, including the Cabo misadventure that some believe cost his team a chance at a Super Bowl. He was replaced by rookie Dak Prescott after being injured in 2016.

Prescott, unlike his predecessor and current backfield mate Ezekiel Elliott, has largely stayed away from Cabo.

Fun fact: tight end Jason Witten, Romo’s friend and teammate, accompanied the couple on their notorious Cabo vacation in 2008. Witten is still with the team in 2019, proving it isn’t necessarily going to Cabo that’s the problem. It’s failing to keep a low profile while doing so.

Cowboys running back Ezekiel Elliott dances down to Cabo every chance he gets. Photo credit: Keith Allison.

Ezekiel Elliott Falls in Love with Cabo & Can’t Wait to Return

If anyone has been less “low profile” about their Cabo San Lucas trips than Tony Romo, it’s Ezekiel Elliott. The fourth overall pick in the 2016 draft, the former Ohio State running back has been nothing short of amazing in his time on the field. In 42 regular season contests to this point, Elliott has averaged 100.3 rushing yards per game. Jim Brown, the man commonly considered the greatest football player of all time, is the only other NFL player to ever average 100 yards a game on the ground. The problem for Elliott hasn’t been production, but rather staying on the field. And no, we’re not talking about injuries.

Elliott’s sophomore campaign was truncated by six games when he was suspended by the NFL for violating the league’s personal conduct policy, allegedly for a domestic abuse incident. This suspension so enraged Cowboys owner Jerry Jones that he effectively waged a shadow war against the commissioner, Roger Goodell, trying to cut both his pay and have him replaced. Elliott, however, was a little more sanguine. After issuing a statement to the press expressing his disappointment and disagreement with the ruling, he went to Cabo to continue training while serving his suspension.

He picked a good spot to do so, holing up at the luxurious Diamante community on the Pacific Coast of Cabo San Lucas, a place home to world-class golf layouts from Davis Love III and Tiger Woods. Elliott’s agent, Rocky Arceneaux, reportedly owns a property there.

Whether it was golf or other recreational activities, Elliott seemed taken with the Cabo lifestyle. Photos surfaced from is first sojourn showing him socializing in a resort swimming pool, from his second on a teebox at the acclaimed Dunes Course.

So taken in fact that when he engaged in a contract holdout with the Cowboys before the 2019 season he returned to Cabo to continue training there away from the team. This holdout was ultimately successfully resolved, with Elliott becoming the highest running back in NFL history courtesy of a six-year, $90 million-dollar extension.

So Elliott got a massive pay raise and got to spend a month in Cabo when his teammates were sweating through training camp.

That’s how you take a Cabo vacation, Tony Romo.


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Chris Sands – Writer  and Michael Mattos



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