In early April, Romo was hired by CBS to be an NFL game analyst. That officially ended a playing career that had exceeded all expectations but his own.
But CBS didn't hire Romo to be just another analyst on a game day roster that goes eight deep. An unproven rookie, he will be the network's lead analyst, replacing Phil Simms, who had been in the seat for 19 years.
Romo will work the network's prime games on Sundays. He'll work prime-time Thursday night games. He'll work the Cowboys' late afternoon game on Thanksgiving, which, if form holds, will be the most watched game of the season. Next season, he'll work the Super Bowl, which is a slam-dunk to be the most-watched TV show of that year.
'Anxious and excited'
But first there is the matter of his first national game. That comes Friday night, when the rookie will analyze alongside veteran play-by-play voice Jim Nantz a relatively meaningless Kansas City Chiefs-Seattle Seahawks preseason game that CBS will broadcast coast to coast.
"I'm anxious and excited," Romo said about his national debut. "It's like my first start in the NFL. I want to see if I'm good enough."
It's not unprecedented that someone who has never worked in a booth debuts as the No. 1. ESPN leading man Jon Gruden worked his first game for the network in 2009. But that was as a co-analyst in a three-man booth. Veteran Ron Jaworski was there as a safety net.
John Madden prepped for stardom alongside Pat Summerall in CBS' and then Fox's lead booth by working for two seasons on lesser CBS games. Before ascending to Fox's lead booth in 2002, Troy Aikman worked the previous season in a lower-tier three-man booth alongside fellow analyst Daryl Johnston and play-by-play voice Dick Stockton. That came only after he spent two summers learning his craft at almost off-the-radar NFL Europe games. And even in his first season on Fox's lead team, the network cautiously put Aikman in a booth with fellow analyst Cris Collinsworth.
CBS Sports boss Sean McManus calls his rookie Romo move "a calculated risk."
"The odds are in our favor," McManus said in an interview. "I don't know if Tony would have come if not for No. 1."
McManus, who has headed up CBS Sports since 1996 and has never worked as a Las Vegas bookmaker, said his network never talked to Romo about any other job on its depth chart.
McManus may have been right about his playbook in recruiting Romo.
Romo said if CBS had not dangled the prime seat alongside Nantz, he'd "most likely still be playing football."
"But I can't be definitive."
The CBS-Romo flirtation started in Arizona in 2015 at the NFL's big annual party on the Friday night before Super Bowl XLIX.
That's when McManus and David Berson, his No. 2, just happened to sit down with the Cowboys quarterback to get his pregame analysis before the New England Patriots met the Seattle Seahawks.
They loved what they heard. They loved his phrasing, his delivery, his lack of jargon, his conciseness and his Cowboys pedigree.
McManus believed he had found an analyst in waiting.
The job interview came in February at the most recent Super Bowl, in Houston. McManus brought Berson and his boss Leslie Moonves, the chairman of the board, president and chief executive officer of the CBS Corp., to a private Saturday meeting with Romo.
Once again, Romo said all the right things.
"After 90 minutes, we came away saying he had all the makings of a great broadcaster," said McManus, who grew up the son of a great broadcaster. His father was Jim McManus, whose professional name was Jim McKay.
And so Romo's life was about to take a turn. He would be walking away from trying to survive in a world where 300-pound men were hungry to make his life miserable and sliding into a broadcast booth where most of the damage is sure to come from armchair analysts and Monday morning critics.
In the wake of the meeting at this year's Super Bowl came two months of serious contract negotiations. A final agreement came in early April.
Romo said CBS' final offer "pushed me to make a decision."
Romo's CBS salary remains classified. A CBS spokesperson said the network never reveals employees' salaries. But it has been reported that Fox would have paid Jay Cutler about $450,000 to work in its No. 2 booth this season. Quarterback Cutler, who retired after the 2016 season, reversed field and signed with the Miami Dolphins for $10 million.
Romo has insisted he won't follow in Cutler's footsteps.
No small part of Romo's final decision was the chance to work alongside Nantz, whose profile he describes as belonging "on the Mount Rushmore of the profession."
"He's the teacher," Romo said. "I'm the student."
On Saturday night, Romo and Nantz were scheduled to work the Los Angeles Rams-Oakland Raiders preseason game.
Jim Rikhoff, CBS' new lead NFL producer, was slated to be in Romo's ear from the production truck. Mike Arnold, the top director, would call the shots. All the regular-season camera operators would be in place. The regular statisticians and spotters were there, too.
It was to have all the makings of a CBS national broadcast. Except no one outside the CBS family would see the broadcast.
It would be Romo's and Nantz's final dress rehearsal.
Perhaps you saw Romo and Nantz working a similar practice game when the Cowboys opened their preseason schedule against the Arizona Cardinals at the Hall of Fame Game on NBC. Al Michaels, Collinsworth and the NBC cameras couldn't ignore the sight of Romo and Nantz working in a distant outpost.
It was the first of three preseason games Romo and Nantz have worked to find a rhythm and comfort zone. In the end, it will be Nantz who is most important to Romo's development.
CBS' entire top NFL crew dissects the videotape of each practice game with Romo and Nantz.
In addition, Romo has called numerous games off videotape in a Dallas-area studio alongside Cowboys radio voice Brad Sham, who was also a key cog in Aikman's development.
The Romo-Sham connection was part of what Romo calls CBS' "boot camp." Former Dallas television sports anchor Tony Martinez, who has evolved into a production whiz, was the head camp counselor. Rikhoff, CBS' lead producer, was also a regular participant.
If Sham or Martinez or Rikhoff were available for comment, he might report how hard Romo has worked at his new craft. Sham and Martinez might testify to how TV Tony, like Aikman before him, is far more glib in front of the camera than he was in front of a locker. But CBS refused to allow anyone who helped Romo, with the exception of McManus, to talk about the process.
NBC's Michaels, however, has talked to Romo and Nantz about the process over the past several months. The three spent some serious time together recently playing a round of golf in Los Angeles.
"The thing I got is Tony is really committed," Michaels said. "I think he will be great on opening night. Still, there is a lot he has to learn."
McManus and Romo agree.
"Tony will be better in Week 6 than Week 1," McManus said. "And obviously, he'll be better in Year 2 than Year 1."
Michaels said he was particularly impressed when Romo raised questions about the difference in lighting between the NBC and CBS booths. Romo also told Michaels he would prefer that Nantz open broadcasts alone, facing the camera, and then invite him in. That's the way Michaels does it at NBC and Joe Buck does it at Fox.
"His attention to detail is astounding," Michaels said of Romo.
Romo said he has also consulted with Collinsworth, Gruden, CBS college analyst Gary Danielson and Phil Simms, his predecessor, about the art of analysis.
But for now, he will prepare just as he did with the Cowboys.
"For me, it's all about improving and working on my weaknesses until they become strengths," Romo said.
An example: "When I was young, I watched the other guys throw at the combine, and I knew I couldn't pass like them," Romo said. "All I had was God-given instincts on the field. I wanted to wake up someday comfortable throwing the ball, putting the ball in the right place. I worked and worked at it and one day I got there.
"That's still the way I'll work my game plan."