They finally settled for Prescott in the fourth round with plans to groom him behind Romo and Kellen Moore.
Who knew the consolation prize would play this season and prove better than any of the other options the Cowboys explored?
"There were questions about him," Wilson said of Prescott. "If he didn't have those, he probably would have been drafted before the fourth round.
"But not drafting Paxton Lynch, not drafting whoever in front of him, and having Tony back, that was just water off his back. That has been very impressive. It just does not matter to him."
The Cowboys liked Prescott, but they liked others better.
They talked to the agents for Colt McCoy and Chase Daniel, but both signed elsewhere for more money. They had Dolphins backup Matt Moore in for a free agent visit, but he, too, wanted more money than the Cowboys were willing to spend.
They inquired about trading with the Rams for Nick Foles but decided the price _ in money and compensation _ was too much.
So the Cowboys' best option became the draft.
Owning the fourth overall pick, the Cowboys flew Paxton Lynch, Connor Cook, Christian Hackenberg, Jacoby Brissett, Jared Goff, Carson Wentz and Prescott to town for pre-draft visits.
On draft day, the Cowboys explored two first-round trades in an attempt to get Lynch after Goff and Wentz went 1-2. But the Broncos drafted Lynch with the 26th overall pick after a trade with the Seahawks.
Jones admitted the Cowboys offered the No. 34 overall choice and the 67th choice to Seattle to move up for Lynch, with the owner saying Lynch had "the highest upside in the draft."
In the fourth round, the Raiders traded ahead of the Cowboys to take Cook. The Cowboys drafted Oklahoma defensive end Charles Tapper with the next choice, No. 101 overall, and finally landed a quarterback _ Prescott _ with a compensatory pick at No. 135.
"We're very fortunate," Cowboys executive vice president Stephen Jones said. "We don't know how Paxton is going to turn out. But obviously with where we sit today, and the job that Dak's doing, I don't know that we would trade him for anybody, including all the quarterbacks picked at the top of the draft.
“We're certainly optimistic about what his future holds, obviously to step in as a rookie, albeit with a great supporting cast. He's just done an unbelievable job for us and certainly his future is bright."
It still took fate, though, for Prescott to move from third on the depth chart into the starting job.
Kellen Moore fractured his right ankle in a training camp practice Aug. 2. Then 23 days later, on the third play of an exhibition game against the Seahawks, Romo was hit by Seattle defensive end Cliff Avril. Romo and the Cowboys received the bad news the following day: He would miss 6-10 weeks with a compression fracture in his back.
That was the moment the Cowboys decided to turn the keys over to Prescott, giving Jameill Showers a chance to serve as his backup.
"The idea really was founded more on our belief that the best way for our team to have a successful season, candidly, was to wait on Tony to get back," Jerry Jones said. "...The thing that we did do was create a situation where these young guys could have an opportunity to literally get more reps than probably their draft status or their free agent status could get."
Prescott won the job he would never relinquish to Romo, and the Cowboys signed veteran Mark Sanchez the week of the season opener to groom Prescott.
"At this level, in general, timing is everything," Sanchez said of Prescott. "You've got to prepare yourself as best you can and then hope things fall into place, whether it's coaching, injuries, the team you're on, the talent around you, all that kind of stuff plays into it, and there's so many factors you can't control. But what he has controlled is everything he could."
Prescott got his first chance as a sophomore at Haughton (La.) High School when senior starter Matt Smith was injured. It took an injury to senior starter Tyler Russell at Mississippi State for Prescott to win the job as a sophomore in college.
Now, it's Romo that Prescott has replaced.
"I don't really like to use the word luck," Prescott said. "It's very unfortunate under the circumstances that I've become the starter. But it's an opportunity, and I'm just trying to make the most of it.
"It's odd. I'll say that. But very unfortunate. It's an opportunity, like I've said. I've never asked why."
Why ask why?
With Prescott's gleaming 13-3 record and rookie-record 104.9 passer rating, the Cowboys are not about to look a gift quarterback in the mouth.
"It was good fortune that we didn't get a chance to draft guys ahead of Dak, but it was bad luck, too, for Kellen and for Tony," Wilson said. "Dak has taken advantage of opportunity, but he's taken advantage of his opportunity at every level. He got his start in high school due to circumstance. He got his start in college due to circumstance. Then, he got a start in the pros due to circumstance.
"It's really crazy luck. There are a lot of the things that could have happened that didn't happen, to our betterment."