Aikman To Mahomes To Dak: Will Cowboys 'Add The Zeroes'?

A Deep Dive Into The Contracts Of Troy Aikman, Patrick Mahomes And Dak Prescott, And A Question: Will Jerry Jones and The Dallas Cowboys 'Add The Zeroes'?

FRISCO - Patrick Mahomes’ historic, half-a-billion-dollar contract compels Dallas Cowboys owner Jerry Jones to show us what he really thinks of Dak Prescott.

Conditionally likes him? Or creatively loves him?

Jones, in case you haven’t been paying attention since 1989, gets what he wants. When and how he wants it. As he’s told us many times through his reign as the most powerful man in DFW sports:

“Every major deal of my life that turned out successful, I’ve overpaid big-time. Never regretted any of them.”

The Kansas City Chiefs wanted their Super Bowl MVP quarterback, so they spectacularly splurged to keep him through 2031. Jones “wants” Prescott, but …

We’ve seen the Hall-of-Fame wheeler-dealer when he genuinely salivates over a goal. Git’r done, indeed.

*Buying America’s Team in 1989, when it was losing $1 million a month.

*Suing the NFL to negotiate his own licensing agreements.

*Tabbing relatively unknown Fox network to be the league’s next big TV partner.

*Signing Deion Sanders and making him the highest paid defensive player in league history.

*Bringing in high-risk Terrell Owens.

*Building a $1 billion stadium in Tarrant County.

*Awarding – when the quarterback had only playoff victory – Tony Romo a six-year, $108 million contract extension that included a $55 million guarantee and $25 million signing bonus.

*And, on Christmas Eve 1993, okaying a Mahomes-like deal to make Troy Aikman the highest-paid player in NFL history:

Eight years. $50 million. $11 million signing bonus.

Turns out it’s simple to quantify inflation in the NFL. Every 25 years or so, just take the total contract of the richest player – Aikman to Mahomes – and simply add a zero. $50 million, meet $500 million.

Jones has until July 15 to ink Prescott to a long-term deal (and avoid renting him in 2020 for $31 million.) In 1993, he had only hours to lock up Aikman before the dawn and restrictions of the salary cap.

“Deadlines,” Jones says now as he said starting back then, “make deals.”

Unlike Romo and Prescott, Aikman was coming off a Super Bowl season. He was the MVP of XXVII, throwing four touchdowns to lead the romp over the Buffalo Bills in the Rose Bowl, and was only a month from leading the Cowboys to another title. A bargain or overpayment? Jones spent only $15 million more to buy the entire team in 1989 than he did to keep his quarterback in 1993.

Aikman was 27 when Jones rewarded him. Prescott will turn 27 on July 29.

Said the owner at the Valley Ranch press conference announcing the landmark deal, “If those dollars are worth it for anyone, they’re worth it for Troy Aikman.”

In essence, the Chiefs are saying that about Mahomes. In reality, Jones is not echoing that about Prescott.

When he won the first of his three Super Bowls, Aikman was playing on a six-year, $11 million contract that made him only the 31 highest-paid quarterback in the NFL. His new contract peaked at $7.5 million in 2000, with an average of $6.25 million per season that broke the previous mark established by the San Francisco 49ers’ Steve Young.

“I was happy with the contract I signed as a rookie, and I’m happy with the contract I have now,” said Aikman, who also went on to a Hall-of-Fame career. “I’m sure there will come a point where someone is making more money than I am now.”

Super Bowl MVP awards aren’t the only link between the bar-raising contracts signed a quarter-century apart by Aikman and Mahomes.

In the 1990s, Leigh Steinberg ruled the NFL as the alpha agent. His stable of stars included Aikman, Young, Warren Moon, Thurman Thomas, Howie Long and Bruce Smith. Early in his unprecedented career, Steinberg represented a record eight first overall draft picks, 11 Hall of Famers, two Super Bowl MVPs and negotiated contracts totaling $3 billion while also donating $750 million to charity.

His image was pristine. His Super Bowl parties were legendary. His life was made into a movie, 1996’s Jerry Maguire.

Then came alcoholism around 2010, shoving him down the slide to personal and professional bankruptcy. Upon rebound in 2013, he had to get re-certified by the NFL Players Association, akin to a Supreme Court judge being forced to re-take the bar exam.

Steinberg enlisted the help of Chris Cabott, a rising agent who helped Leigh discover sobriety. Cabot began scouting Mahomes during the quarterback’s freshman season at Texas Tech. He called Mahomes’ mother at work and struck up a relationship that ultimately landed the future MVP with Steinberg’s comeback, fledgling agency.

“I mean, he was always upfront and honest with me and believed in me, and he and Chris had a plan for me going into the draft,” Mahomes said before the 2019 season. “It really came down to trusting those guys and seeing what they had planned for me.”

“He’s the godfather of our industry,” Cabott said of Steinberg. “That will never change.”

With the Mahomes deal, Steinberg, 71, now has on his resume three contracts that were the richest in NFL history at the time, and one remarkable rally.

“People talk about the comeback, but my real comeback is having been a good parent and maintaining continuous sobriety,” Steinberg said. “I didn’t do it alone. If there are people out there struggling and hopeless because of some form of substance addiction, there are 12-step programs and unique fellowships that can help. There’s a light at the end of the tunnel. The reason I’ve been public about it, the alcoholism, is it might inspire someone to help find a path forward.”

With Steinberg’s handiwork, Mahomes in the first half-billion-dollar athlete in American history, his new contact eclipsing baseball star Mike Trout’s previous standard of $425 million.

The domino effect could frame Jones’ negotiations with Prescott. For one, the owner no longer has to worry about the optics of giving a record contract to a quarterback with only one postseason (Wild Card) victory.

Prescott isn’t in Mahomes’ class as a quarterback. Nor Aikman’s. And, for that matter, neither is he on par with the Seattle Seahawks’ Russell Wilson. As CowboysSI.com was first to report, the Cowboys have already proposed a Wilson-esque five-year, $35 million contract. Prescott wants a four-year deal that would allow him a shorter path to a second break-the-bank deal.

The Chiefs so wanted Mahomes – and vice-versa – that they got creative. With years. With money. With a new football term: “guaranteed mechanisms.”

There is now a way for a Dak deal in Dallas. But does Jones truly have the will?