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The Pretty Good Life of Tony Romo

In praise of the soon-to-be-departed Cowboys QB, who was one of the easiest Dallas athletes to like and one of the hardest and most frustrating to pin your hopes on

(Getty Images/Ringer illustration)
(Getty Images/Ringer illustration)

On December 28, 2008, Tony Romo told us everything we needed to know about him. It was Week 17. The Cowboys had just lost to the Eagles by 38 points and were out of the playoffs. “If this is the worst thing that will ever happen to me,” Romo told reporters, “then I’ve lived a pretty good life.”

That one sentence created Tony Romo — or, at least, Tony Romo’s image. There was the aura of pretty-goodness that trailed Romo for years; his seemingly casual attitude toward the serious business of football; and the unexpected Zen that allowed Romo to step aside when Dak Prescott took away his job. Now that Romo is being released, we can see his Cowboys legacy more clearly. Romo was one of the easiest Dallas athletes to like and one of the hardest and most frustrating to pin your hopes on.

In 2003, when Romo came out of Eastern Illinois University, he was pro football’s equivalent of a preferred walk-on. There was a minor recruiting battle thanks to the concentration of ex-Panthers then coaching in the NFL: Mike Shanahan, Brad Childress, and Sean Payton, who was an assistant with the Cowboys. Romo got a signing bonus of $10,000. He took the no. 9 because it was the cursed slugger Roy Hobbs’s number in The Natural, Sports Illustrated’s S.L. Price reported. Romo wore his baseball caps backward. He smiled a lot more than Troy Aikman.

“If I had put in Romo in his first year and just let him play,” Bill Parcells once said, “he would have been out of football in a year and a half. He was just a gunslinger. He was indiscriminate. And he would do shit that you just can’t succeed doing. But after a year or two of practicing in the preseason, getting his [reps], you could see he had a real good chance to come along.”

When Romo became the starter in 2006, he was hailed as a savior. Here was the end of the wilderness years when Cowboys fans tried to talk themselves into Drew Henson. But in the playoffs against Seattle that season, Romo dropped the snap on a go-ahead field goal attempt, the Cowboys lost, and Parcells was driven out of coaching for good. (It was Romo’s luck that, on the play before, he threw a pass that got the Cowboys first-and-goal on the 1-yard line. The refs overturned the call.)

The next year, Romo’s Cowboys went 13–3 and earned the no. 1 seed in the NFC. For the bye week, Romo took his then-girlfriend Jessica Simpson and Jason Witten to Cabo San Lucas. (Cowboys fans would insist I mention that scrub linebacker Bobby Carpenter was also along for the fiesta.) In terms of the bonkers media reaction it produced, it was the original Giants boat ride. When the Cowboys were upset in the first round, no less than Aikman leveled Romo.

An idea took hold. Romo might be a pretty good quarterback but he was a defective one: good enough to dodge defenders and throw for a lot of yards, but lacking a certain Aikmanesque intangible to win the big game. And Romo just seemed distractible. He loved golf and tried to qualify for the U.S. Open. He dated starlets like Simpson and Carrie Underwood. (Never mind that Underwood said they broke up because Romo cared too much about football.) Like I said, Romo smiled a lot.

Then came December 28, 2008. Romo threw an ugly pick and had a fumble returned for a touchdown. Then he told the press that there was more to life than a wild-card berth.

Has any comment other than “no más” undermined an athlete so effectively? Dallas media types who take their jobs no more seriously than Romo blasted away. “The Cowboys aren’t losing Troy Aikman or Roger Staubach,” sports anchor Dale Hansen said last November. “They’re losing Danny White.” Moreover, the lovably goofy Romo disappeared overnight. Writers such as The Ringer’s Bill Simmons like to talk about Romo’s great future in sports television. But other than his November speech, Romo hasn’t said anything interesting in a nearly a decade.

These days, football fans are smart enough to know that calling Romo a loser, full stop, was unfair. Win-loss record is a sloppy way to judge a quarterback, especially when Jerry Jones is selecting the quarterback’s supporting cast. The Cowboys front office later wrestled away some decision-making from Jones; Romo got to play only one full season behind the Cowboys’ vaunted offensive line.

The idea that Romo was actually one of the NFL’s best quarterbacks took years to enter the popular consciousness. There was the woodpeckering of analytics writers like Bill Barnwell, plus Price’s 2013 SI cover story, the headline of which proclaimed: “Why America’s Whipping Boy Deserves Your Unconditional Love.”

Romo got exactly one year to lap it up. It probably says something about us Cowboys fans that we enjoyed 2014 — it’s his most un-Romo-like season. He handed off to DeMarco Murray and tried not to make mistakes. (He still led the NFL in yards per attempt and completion percentage.) Then … Romo got hurt again, and the game he missed cost the Cowboys the no. 1 seed. Against Green Bay in the playoffs, there was the Dez Bryant non-catch, a Murray fumble, etc. Romo didn’t have to live with his old caricature but he didn’t bring home a ring, either.

The silent coup that got Dak Prescott the job this year was notable for its smoothness. If a single Cowboys player complained that a 10-year starter and perennial Pro Bowler didn’t get a chance to win his job back, I must have missed it. The opposite happened: anonymous sources warned that the Cowboys locker room would come apart if Prescott got benched.

Without further smearing Romo, I think this was pretty telling. Some of his estrangement from the Cowboys was normal: Romo was 15 years older than, say, Zeke Elliott, and, with a cap hit edging past $20 million, made a lot more money. Romo was no longer taking vacations with Jessica Simpson. He was taking vacations with head coach Jason Garrett — a decision whose wisdom I’d love to hear Garrett explain some day. Plus, Cowboys players had suffered through Romo’s most soul-crushing losses (and even more frequent injuries). It’s probably a lot to expect NFL players to defer to analytics.

Romo’s step-aside speech on November 15 was a miracle — arguably his greatest moment as a Cowboy. He spoke in the second person voice of a self-help pamphlet: “You’re sad and down and out, and you ask yourself, ‘Why did this have to happen?’” The preseason injury he suffered against the Seahawks, Romo said, put him in a “dark place.” He added, “The press is whispering. Everyone has doubts.”

Romo’s injury and benching was as unfair as anything that had happened in his star-crossed career. And yet: “football is a meritocracy …” Romo said. Prescott “earned the right to be our quarterback. As hard as that is for me to say, he’s earned that right.”

Can you imagine Tom Brady stepping aside in the middle of a Super Bowl run for Jimmy Garoppolo? Of course not. The same supposedly faulty wiring that made Romo an imperfect NFL QB offered him the pathway to an unusual kind of grace. Note also that Romo’s message that there’s more to life than football is exactly what he was saying back in 2008. This time, because the Cowboys had a cheap, young quarterback in the fold, we were all willing to listen. If rooting for Tony Romo is the worst thing that will ever happen to us Cowboys fans, then we’ve lived pretty good lives.