Jones can point to second-round gambles -- just with the players currently on the Cowboys' roster -- that have paid off perhaps more than most thought despite some issues that remain.
In 2010, the Cowboys had linebacker Sean Lee rated as a first-round pick on their draft board. They knew he had a partially torn anterior cruciate ligament in his left knee that might fully tear and require surgery. With the No. 55 overall pick, the Cowboys drafted Lee, who missed his third season at Penn State with a torn ACL in his right knee. While he battled through injuries throughout his career, the left ACL did not tear until 2014.
In 2015, the Cowboys viewed Randy Gregory as one of the best pass-rushers available in the draft. Off-field issues and a failed drug test at the NFL scouting combine kept Gregory from being selected in the first round, but the Cowboys took a chance on the defensive end with the No. 60 overall pick.
In 2016, outside linebacker Jaylon Smith was off a number of teams' draft boards because of a serious knee injury he suffered in the Fiesta Bowl while playing for Notre Dame. There was a risk of permanent nerve damage that could have ended Smith's career before it even began. But one of the Cowboys' team physicians, Dr. Daniel Cooper, performed Smith's surgery and was confident Smith could return at his top level some day. With the No. 34 overall pick, the Cowboys chose Smith, knowing he would not play his rookie season.
Smith finished second on the Cowboys in tackles in 2018, played in 32 straight regular-season games and has the potential to be a yearly Pro Bowl pick. When healthy, Lee has been one of the Cowboys' best defenders since the Cowboys picked him. He made the Pro Bowl in 2015 and '16. Gregory's issues remain and he is suspended indefinitely, but he showed he still has a chance to deliver on his pass-rush promise with six sacks last season.
If there was one commonality between those three drafts (2010, 2015 and 2016), it's that the Cowboys had a first-round pick in each of those years, taking Dez Bryant before Lee, Byron Jones before Gregory and Ezekiel Elliott before Smith.
The Cowboys did not make a pick in Thursday's first round because of their trade for Amari Cooper last October with the Oakland Raiders.
"I think you're operating without a net a little bit," Jones said when asked about making a risky second-round selection in 2019. "By not being able to have [drafted in the] first round someone you hope gives you a contribution in the first year, if you start going into the second pick with a real question mark as to this coming year's contribution, I think logic would dictate for me slowing down a little bit there."
But there is always a never-say-never when it comes to Jones and the draft.
He will take chances other general managers will not make because he carries the title of owner as well. He has lifetime job security, but he also believes it allows the franchise to act more quickly in times that require immediate answers.
"It's always, frankly, about the gain and a little diminished thought about the price or the cost," Jones said. "So -- if you will, [you] candidly always look to the positive. Amari is the perfect example, as opposed to the consequences of not having him. Scarlett O'Hara, she looked at Rhett Butler, 'I'll worry about that tomorrow.'"
Jones, however, has to think about tomorrow even more and not just because Dallas did not have a first-round pick. He has to think about the money he will lay out over the next few years, starting with the $105 million deal given to DeMarcus Lawrence earlier in the month and the millions he will likely have to guarantee to keep Dak Prescott, Cooper, Elliott and Jones.
In a perfect world, a second-round pick becomes a starter and a player signed to a second contract.
Not all of Jones' second-round chances, either through off-field issues or injury, have panned out, though. Quincy Carter (2001), Antonio Bryant (2002), Al Johnson (2003) and Bruce Carter (2011) are prime examples. Also, second-round picks Jacob Rogers (2004) and Gavin Escobar (2013) did not work out.
The Cowboys need to hit on their second-round pick -- and really most of their middle-round picks, too -- to help manage their salary cap over the next four years. Those relative low salaries, even if a portion of second-round money is guaranteed -- give the team a chance to map out their salary-cap plan when the top end of the roster will earn big money.
A portion of second-round money is guaranteed but the four-year security of those salary figures matters. The top 10 earners account for 57.91 percent of the cap room. That percentage will rise when/if Prescott, Cooper, Elliott and Byron Jones sign long-term deals.
"We have to be good all the way through the draft," said executive vice president Stephen Jones, who puts together the Cowboys' cap puzzle. "I know that's easier said than done, especially as we start to get into this world of having some really high-priced players, well-deserved albeit. But as we start to have these bigger contracts, then we are going to have to have these draft classes step up because there's going to be situations where we can't sign them all. We want to do everything we can to manage it. We think we've got a great plan in terms of how we're going to move forward to optimize this particular roster. We think it's a young roster that has the potential to win championships. But we have to manage it in a good way."
And it starts with making a risk-averse pick with the 58th overall pick on Friday.