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Sean Payton wasn’t able to get Tony Romo on the Saints. What if he had?

Would Romo have won a Super Bowl ring with Payton?

By James Brady

Sometimes, one play, one moment, one decision can change everything — or maybe only a little bit. Either way, it can be fun to imagine the various timelines if one thing had gone differently. SB Nation NFL is looking at those hypotheticals, alternate universes, and made-up scenarios in our second annual “What If?” week. You can follow along with every story here.

Tony Romo never led the Dallas Cowboys to a Super Bowl, but he did put together a pretty prolific career quarterbacking one of the most storied franchises in the NFL. His accomplishments include four Pro Bowls, a second-team All-Pro selection, and owning the Cowboys’ franchise records in passing yards, passing touchdowns, passer rating and game-winning drives — all more than Troy Aikman.

But unlike Aikman, Romo never got a ring. Would he have been able to hoist the Lombardi Trophy if one single deal, early in his career, went another way?

In 2015, former NFL coach and executive Bill Parcells put out a biography, and among the details that were revealed was just how close the New Orleans Saints were to trading for Romo while Parcells was still the head coach in Dallas.

Under Parcells from 2003-05, Sean Payton was the Cowboys’ quarterbacks coach and then their passing game coordinator. Like Payton, Romo had played quarterback at Eastern Illinois, and Payton helped persuade Romo to sign with the Cowboys after he went undrafted in 2003, despite some heavy competition.

Payton was hired as the head coach of the New Orleans Saints in 2006. During the offseason, Payton offered a third-round draft pick for Romo, which would have been a pretty good return for Dallas then. At that point, Romo was still Drew Bledsoe’s backup and had yet to throw a pass in the NFL.

But there were enough people in the organization who saw something in Romo that the Cowboys would accept nothing less than a second-round pick, according to Parcells’ book. And it’s a good thing that the Cowboys held firm on that — Romo replaced Bledsoe halfway through the 2006 season and stayed the starting quarterback until Dak Prescott came along a decade later.

The Saints, though, wound up doing pretty well without Romo. After the Romo trade fell through, they signed free agent Drew Brees. In his time in New Orleans, Brees has been one of the best and most consistent quarterbacks in the league. He led the team to a Super Bowl win during the 2009 season and is on his way to the Hall of Fame once he hangs up the cleats.

What would have changed for Romo and the Saints?

Could that ring have been Romo’s? Could the Payton-Romo connection have been as exciting or successful as the Payton-Brees connection has been? For the sake of argument, we’ll assume that New Orleans offering a third-round pick was enough of a commitment for the team to also not pursue Brees in that same offseason.

And comparing the two quarterbacks, you’ll find that many of their career stats line up, even if Brees’ numbers are ultimately higher because he’s had a longer career and has attempted far more passes. The ratios and percentages are very similar:

Drew Brees, 18 seasons: 67.3 completion percentage, 520 TDs vs. 233 INTs, 7.6 YPA, 97.7 passer rating
Tony Romo, 13 seasons: 65.3 completion percentage, 248 TDs vs. 117 INTs, 7.9 YPA, 97.1 passer rating

In 2009, the year Brees and the Saints won Super Bowl XLIV, Romo had a pretty good season. He completed 63.1 percent of his passes for 4,483 yards, 26 touchdowns, and nine interceptions. He made the Pro Bowl and helped the Cowboys finish with an 11-5 record and an NFC East title, as well. In the playoffs, Romo led them to a win over the Eagles, but fell to the Vikings in the Divisional Round. In other words, he was one game away from facing Payton and Brees.

There’s also the perception that Brees is a clutch player and Romo is not because of their playoff records, which is honestly pretty silly. Yes, Romo had a couple high-profile blunders, like the botched hold in Seattle, but he also posted more fourth-quarter comebacks (23) and game-winning drives (27) than any other quarterback from 2006 to 2014.

In the playoffs, Romo’s numbers are much smaller and not as impressive as Brees’, but he’s still not that far off:

Brees, 15 playoff games: 8-7 record, 66.3 completion percentage, 33 TDs vs. 11 INTs, 7.7 YPA, 100.0 passer rating
Romo, 6 playoff games: 2-4 record, 61.6 completion percentage, 8 TDs vs. 2 INTs, 7.1 YPA, 93.0 passer rating

So it’s pretty easy to see that Romo would have been productive in Payton’s offense. He likely would’ve found more success with the Saints in the postseason than he did with the Cowboys — and perhaps even led them to a Super Bowl win like Brees did.

What would’ve happened to Brees then?

If the Saints had no need for Brees, where would he have gone in the 2006 offseason? Brees was coming off a career year with the Chargers, but he was now a free agent and the Chargers had already committed to Philip Rivers as their quarterback of the future.

At the time, the teams reportedly interested in Brees were the Saints and the Miami Dolphins.

Nick Saban, then the coach of the Dolphins, was big on Brees. He was the first choice for Miami, but Brees picked the Saints (and was happier for it). But if Brees doesn’t sign with New Orleans, then Miami is looking like a pretty good place to play. Does Brees extend the length of Saban’s troubled NFL head coaching career?

Eventually, the Dolphins traded — what else — a second-round pick for Daunte Culpepper, who washed out of the league not long after that.

The Vikings were likely always going to trade Culpepper so that doesn’t factor much into the scenario, but he could have landed elsewhere, which would have impacted ... pretty much any team in the market for a quarterback in 2006.

To sum it up, we have a potential Romo-Payton Super Bowl in New Orleans, a potential period of success for Nick Saban and the Drew Brees-led Dolphins, and a mystery third team giving up a second-round pick for Culpepper. Oh, and the Cowboys would still have been on the hunt for a franchise quarterback.

Or do you think it would have shaped up differently?

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