Each showed outstanding regular-season success but left lingering questions in the playoffs.
They were teammates for one season, 2016, when the rookie Prescott took over after Romo suffered a preseason back injury. Prescott has held the job ever since.
They share a beloved underdog narrative; Romo as an undrafted free agent, Prescott as a fourth-round pick. They were selected for multiple Pro Bowls. They set team records. They used the power of their position with “America’s Team” to become household names.
Romo had three chances to advance to an NFC Championship Game (2007, 2009, 2014) and never got there. Prescott’s chance at a fourth try was wiped out by the Packers after missed chances in 2016, 2018 and 2022.
“It’s not fair to put it all on Dak or Tony,” one former teammate of both said. “Everyone needed to get it done.”
While true, the Cowboys’ quarterback bears the brunt of the responsibility.
SINCE 1980, KEN Anderson is the only quarterback to be his team’s starter for more consecutive seasons than Prescott will have in 2024 (nine) before going to a Super Bowl for the first time. He was in his 10th season as the Cincinnati Bengals‘ starter in 1981.
Peyton Manning and Matt Ryan made their first Super Bowl appearances in their ninth seasons with the Indianapolis Colts and Atlanta Falconsrespectively. Manning had won two NFL MVPs before getting to his first Super Bowl in 2006 and had to contend with Tom Brady and the New England Patriots‘ dynasty.
“Some guys, like Troy, it does happen right away and you win championships,” said executive vice president Stephen Jones about Aikman’s first Super Bowl coming in his fourth season. “[Patrick] Mahomesguys like that, it happens for them.
“But there’s other guys that sometimes it just takes time to keep learning the game, keep getting better. Certainly I think Dak fits in that category, and I think Tony was in that category before the injuries.”
Age favors Prescott’s opportunity for at least another run.
Romo was 34 for his final chance in 2014, his last full season, with a body that was faltering mainly because of back issues that required multiple surgeries.
While the lasting memory from that 26-21 divisional round loss to the Packers is the overturned catch from Dez Bryant late in the fourth quarter, there was one of Romo that day too. About an hour after that stinging defeat in numbing temperatures outside Lambeau Field, he shared a long hug with his family before getting on the team bus, as if he knew he would not get a better chance.
Prescott turns 31 in July and played every game this season for the first time since 2019, while leading the NFL in touchdown passes (36). Like Romo, he has suffered serious injuries, like a dislocated and fractured right ankle in 2020, and a broken right thumb that forced him to miss five games in 2022, but he believes his off-field habits have made him stronger and more durable.
“You’re always looking at greats and what they’re doing, and you see guys, like LeBron [James]Tom Brady, have these methods and spend millions of dollars on their body each year, and you wonder why,” Prescott said. “And it’s obvious when they’re playing as long as they played at such a high level that that’s what they need to do to feel comfortable.”
THE BIG QUESTION for the Cowboys regarding Prescott this offseason is not health, but contract.
He is about to enter the final year of his deal and will count $59.4 million against the 2024 salary cap. Dallas’ options this offseason include:
Extending Prescott’s contract, which would make him among the highest-paid quarterbacks in the NFL but give them space to retain their own players or add free agents.
Simply playing out Prescott’s final year, knowing they cannot use the franchise tag on him in 2025, which would make him an unrestricted free agent.
Adding more voidable years to his contract to make his 2024 cap number more palatable, while also knowing they will add more dead money against the cap in future years.
In 2013, the Cowboys faced a similar contractual dilemma with Romo. They could not place the franchise tag on him due to contractual language, and he signed a six-year, $108 million extension through 2019 that included $40 million in guaranteed money. At the time of the signing, the $18 million annual average made Romo the sixth-highest paid quarterback.
Like Romo then, Prescott now holds leverage in the negotiations — although, unlike 2013, the Cowboys have a young quarterback who intrigues them in 2021 No. 3 overall pick Trey Lancewhom they acquired from the San Francisco 49ers early this season for a fourth-round draft pick. Lance, 23, did not take a snap this season and has 102 career pass attempts.
Three years ago, Prescott outlasted the Cowboys in contract talks, turning one year of playing on the franchise tag into a four-year, $160 million deal that included $126 million guaranteed despite coming off the serious ankle injury. His $40 million annual average currently has him tied for 10th among the highest-paid quarterbacks.
Owner and general manager Jerry Jones, as well as Stephen Jones, have said they envision Prescott being the Cowboys’ starter well into the future.
But will that future include a Super Bowl appearance?
JERRY JONES SAID his biggest regret as owner and general manager is not winning a Super Bowl with Romo as quarterback. After beating the Philadelphia Eagles in December, Jones said he would be “equally” disappointed if Prescott doesn’t get to a Super Bowl.
“Dak is a player who is qualified in every way to have a Super Bowl in his career,” Jones said then.
Romo’s best chance for a Super Bowl run was in 2007 when the Cowboys finished 13-3 and had home-field advantage in Wade Phillips’ first season as coach. The Cowboys lost in the divisional round to the New York Giantswhom they had beaten twice in the regular season and went on to win the Super Bowl.
In 2014, when Romo had his best season, he was in his ninth year as the Cowboys’ starter (eighth full season). The Cowboys went 12-4 and won the NFC East. He threw 34 touchdown passes and was intercepted just nine times in 15 starts. He led the NFL in completion percentage (69.9%), QBR (79.2), quarterback rating (113.2) and yards per attempt (8.5).
In 2015, Romo broke his left collarbone twice and started four games. In 2016, he suffered a back injury in a preseason game against the Seattle Seahawks and played one regular-season drive — a touchdown drive — because Prescott played so well. By 2017, Romo joined the CBS broadcast booth.
“I know deep down he felt he was at his best mentally when it came to the game, that if he was healthy, he could play the game as well as he ever could,” Stephen Jones said. “But health got him.”
Prescott just concluded his eighth full season as the Cowboys’ starter. Dallas went 12-5 and won the NFC East. He led the NFL in touchdown passes with 36 and was intercepted nine times. Among full-time starting quarterbacks, he led the NFL in completion percentage (69.5%) and was No. 2 in QBR (72.9), quarterback rating (105.9) and passing yards (4,516).
The Cowboys were set up for a run to the NFC Championship Game with two home games at AT&T Stadium as the No. 2 seed, only to flail away Sunday. Prescott was intercepted twice in the first half, including one that was returned for a touchdown and upped Green Bay’s lead to 27-0 late in the second quarter.
FOR ALL OF his regular-season success, Prescott has not been able to match that level in the postseason. It’s something Romo did not do either.
That leaves the lingering question: “Why?”
“It’s tough to give you that answer when I just went out there and we just did that,” Prescott said. “Unfortunately, that’s what the offseason is for — and it’s a long one. Yeah, I wish I could give you that answer.”
Prescott’s performance against the Packers was unlike any under the big-picture view of a 17-game regular season.
“Dak’s arrow is still straight up,” Stephen Jones said a few days before the Packers loss. “I think the best football is in front of him. He keeps getting better, and then he has all the other intangibles that go with his skill set, which is plenty strong to being special.”
But Prescott knows what Romo knew before him: Nothing matters if you don’t win a Super Bowl in Dallas.
“It’s about winning and winning the playoffs,” Prescott said after the Packers loss, “and getting to the last game and winning that as well.”