
The Cowboys’ path to finding franchise quarterbacks throughout this century has been pretty unique.
When you look at the history of the Dallas Cowboys, there is a never-ending list of great stories. We could go on forever discussing how certain players ended up in Dallas and explore so many different hypotheticals that it could drive fans crazy.
Speaking of crazy, something that is crazy to think about is how close the Cowboys came to not having one of their four most talented quarterbacks over their 65-year existence. If you examined each situation, there were instances in each case that almost made it to where the legacy we have come to appreciate never happened. Let’s brush off some cobwebs and take a stroll down memory lane.

What if Landry didn’t have the patience to wait for Staubach?
Starting with Captain America himself, the Roger Staubach story has several what-ifs along the way. The team took a flyer on him, drafting him in the 10th round of the 1964 draft, however, Staubach wouldn’t step onto the field until five years later due to his commitment to the Navy. He even used his military leave to show up at Cowboys rookie camp. And when he finally did arrive in Dallas, he found himself in a quarterback battle with Craig Morton. In fact, it was a timeshare unlike any other, as head coach Tom Landry would alternate between the two QBs within the games. It wasn’t until Staubach’s third season in the league at the age of 29 that he finally took over as the team’s undisputed starting quarterback, where he led the Cowboys to four Super Bowls, winning two of them.
What if Jimmy sided with Walsh over Aikman?
From one Super Bowl-winning Hall of Fame quarterback to another, the team selected Troy Aikman number one overall in the 1989 NFL draft. Unlike Staubach, Aikman started right away, and it was rocky to say the least. Jimmy Johnson inherited a terrible team from the legendary Landry, and they finished 1-15 in their first season. Despite their draft investment in Aikman, Johnson loved his former Miami Hurricane quarterback Steve Walsh and selected him second overall in the supplemental draft that same year. Aikman missed five games in his rookie season, and Walsh stepped in and helped Dallas win their only game of the year. In the end, Walsh was traded to New Orleans a year later, but Jimmy’s love for his former college quarterback created some uncertainty as to what direction they might go.
What if Romo was traded to the Saints?
The Cowboys were in quarterback purgatory after Aikman retired, and it wasn’t until Tony Romo showed up that new life emerged. Actually, it was four years after he arrived before Romo-mania took off. That’s because he was an undrafted free agent who was buried on the depth chart for his first few years in the league. After some impressive pre-season outings, some took notice, including his former quarterback coach Sean Payton, who had just become the head coach in New Orleans. Payton offered a third-round pick for Romo, but Jerry Jones wouldn’t give him up for anything less than a second-round pick. A deal was never done, and by Week 6 of the 2006 season, a new era in Dallas had begun as Romo took over the starting job, replacing Drew Bledsoe.
What if the Cowboys never drafted Dak?
Fast forward ten years, and we find ourselves in another unexpected passing of the torch at quarterback. After the Cowboys missed out on two of their QB targets in the draft, Paxton Lynch and Connor Cook, they eventually “settled” on Dak Prescott at pick 135. Prescott entered his rookie season fourth on the depth chart behind Romo, Kellen Moore, and Jameill Showers. Injuries to Romo and Moore opened the door, and Prescott’s performance moved him to the top spot by the start of the regular season. And he never let go. Prescott had an impressive rookie season. It was so good that Jason Garrett made the tough decision to stay with Dak even after Romo was healthy again, leaving Cowboys fans with one of the biggest hypotheticals in franchise history…
What if Romo got one final shot?
What do you think happens if the Cowboys roll with Tony Romo in the playoffs in 2016? Do things work out better for Dallas? Worse? No change?
Romo looked sharp during his final drive in a Cowboys uniform. pic.twitter.com/MiC7OOyk8Z
— Dan Rogers (@DannyPhantom24) June 1, 2025
What do you think happens? It’s tough to answer. Romo had a checkered past of up and down playoff moments, but his last two playoff games in 2014 were pretty solid. He had settled down and wasn’t making as many reckless decisions. Prescott was young, but he was pretty calm and collected. He played well against the Green Bay Packers in the divisional round in 2016, leading a comeback charge despite falling into a hole. Obviously, the Cowboys came up short in that game, so it’s easy to just say they should’ve gone with Romo, but it would have been hard for him to have put together a better game to produce a more favorable outcome. The Cowboys lost that game, but it wasn’t because of Dak. There’s a slight chance it might’ve gone better, but there’s an even greater chance there was no change, or even worse.
The Cowboys’ quarterback situation has had so many crazy backstories that go back many decades. Even the Danny White/Gary Hogeboom QB controversy was something fans of the ‘80s had to endure. We can point to so many different instances where the franchise was super close to leaning the other way, and it could’ve meant the legacy of some of our all-time favorites never happened.