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Dallas Cowboys owner Jerry Jones' mentality when it comes to roster management has long been "staying in the middle and picking your shots with risk-taking." Now, Dallas is entering a period where it's time to pay top dollar for some of its top homegrown players or move on. 

It's players like two-time Pro Bowl quarterback Dak Prescott (two years remaining on a four-year, $160 million deal); 2022 second-team All-Pro wide receiver CeeDee Lamb (two years remaining on rookie deal, including a $17.99 million fifth-year option in 2024); two-time Pro Bowl cornerback Trevon Diggs (entering final season of rookie deal); and two-time first-team All-Pro linebacker Micah Parsons (two years remaining on rookie deal) who are awaiting new deals.

On Tuesday, the first day of Cowboys training camp, Cowboys COO and EVP Stephen Jones expressed optimism about Dallas' current cap situation, indicating the team is open for business on contract extensions for Parsons, Diggs, Lamb, and 26-year-old right tackle Terence Steele, per SB Nation. The Cowboys currently have $20.7 million in cap space for the upcoming 2023 season, the fourth-most in the NFL and $24.4 million in room for 2024, according to OverTheCap.com. 

"I actually feel really good about where we are, not only in the intermediate but also in the long term," Jones said Tuesday. "We're very motivated to sign these young guys."

This is a sentiment Jones has had since the early portion of the Cowboys offseason program. 

"That group, we feel really good about, and I feel as we move forward it will all be about timing," Jones said back in May, via The Athletic. "We feel good that we can work within the parameter of the cap and make those types of things happen. We have to continue to do well in the draft to make things like that happen. We have to continue to have guys step up and play because along the way, if we want to do those [deals], then we'll have to make some tough decisions in other spots. ... We want to work on all of the above, but we'll just have to see how this thing plays out. You can't dictate when things happen and the timing. It takes two sides. For them to want to sign up, they've got to be happy where it is. And vice versa. But I wouldn't say just because we don't get it done by the start of the season doesn't mean we're not going to ultimately sign them."

Lamb and Diggs, Dallas' first two picks in the 2020 NFL Draft, both voiced their enthusiasm earlier this month for locking down a long-term future with the Silver and Blue.

"I'm very excited," Lamb said in May, via The Athletic. "Dallas is somewhere I've always wanted to be. I don't see myself really wearing any other jersey. I don't really want to get into too much detail on that, but I'm definitely excited for the future."  

"Hopefully something gets figured out," Diggs said. "I love Dallas. I love being here, so, you know, we'll see. 

Since Diggs was a second-round pick, the fifth-year option wasn't available for him, but the Cowboys could opt to franchise tag him like they did running back Tony Pollard this offseason. The top of the cornerback contract market in terms of total value belongs to Denzel Ward of the Cleveland Browns ($100.5 million) while the top contract at the position in terms of average-per-year belongs to Jaire Alexander of the Green Bay Packers ($21 million). Alexander, Ward ($20.1 million) and Miami Dolphins cornerback Jalen Ramsey ($20 million) are the only cornerbacks in the NFL making an average of $20 million annually. 

In Lamb's case, there are 14 receivers making at least $20 million on average, with the biggest total value deal belonging to Davante Adams of the Las Vegas Raiders ($140 million) and the biggest average-per-year contract belonging to Tyreek Hill of the Miami Dolphins ($30 million). 

"It's not daunting," Stephen Jones said when addressing the cornerback and wide receiver markets in negotiations, per ESPN. "I think it's doable. It's just part of managing your football team, a part of managing the salary cap. But I certainly think it's doable."

Parsons is the last of the bunch of Cowboys' early-round draft picks in line for a generational payday, and his contract will certainly end up being more sizable than what Diggs and Lamb can command. The 23-year-old co-led the NFL in quarterback pressures (90) last season with 2022 Defensive Player of the Year and San Francisco 49ers defensive end Nick Bosa, while his 13.5 sacks ranked seventh in the NFL, five behind Bosa's league-leading 18.5. As a rookie, Parsons still wreaked havoc in opposing backfields, totaling just one-half sack fewer in 2021 (13.0). His pass-rushing chops have earned him first-team All-Pro nods each year. 

After some back and forth in the media about whether his position is defensive end, which is what Parsons said, or linebacker, which is what defensive coordinator Dan Quinn said, Stephen Jones declared that regardless of what the team thinks Parsons' position is, he's going to get paid. Chargers outside linebacker Khalil Mack holds the biggest contract by a defensive player in terms of total value ($141 million), while three-time NFL Defensive Player of the Year and Rams defensive tackle Aaron Donald is the owner of the highest average annual salary of any defensive player ($31.7 million). 

"Micah is a great player," Stephen Jones said. "He's a great defensive football player. Whether he gets 10-plus sacks a year at linebacker or defensive end, I don't think it's a big difference. Micah is kind of a hybrid player. That's what makes him great, he's versatile."

Prescott is in a different boat than his teammates in their early- and mid-20s, as the soon-to-be 30-year-old (his birthday is July 29) is seeking his third NFL contract from the Cowboys. He also had to play through the franchise tag in 2020 prior to receiving his current four-year, $160 million extension back in 2021.

It would behoove Dallas to get a deal done with its face-of-the-franchise quarterback sooner rather than later because his cap number is currently set to jump from $26.8 million in 2023 to $59.5 million in 2024, a figure that's likely going to make it untenable for the Cowboys to juggle the rest of the contracts mentioned above under the salary cap going forward. Stephen Jones feels like this negotiation will go a lot smoother than the drawn-out, multi-year standoff that occurred when Prescott went from being paid like the fourth-round pick that he was to earning top-of-the-market quarterback money. 

"We're already at a big number with Dak," Stephen Jones said. "So, when the really daunting part comes is when you move them from a rookie contract to making the type of money quarterbacks make now."  

There are now 11 quarterbacks who make at least $40 million as an average annual salary, something that was much more exclusive when Prescott signed the deal just a couple years ago. Baltimore Ravens quarterback Lamar Jackson ($52 million average per year) and Philadelphia Eagles quarterback Jalen Hurts ($51 million average per year) have reset the position's market this offseason, joining New York Jets quarterback Aaron Rodgers as the only players who make at least $50 million on average each season. While it's generational wealth, Prescott said earlier this month that he personally stays out of those contract discussions with the front office. 

"That's stuff I leave to the Cowboys, and I leave to my agent," Prescott said in early May. "They got it done years ago and when it comes time to get it done again, I trust in both of them. And as Stephen said, it might happen overnight, who knows? But that's not any of my concern or in my thought process."