So while he tries to put a championship-caliber team together this season, he must be cognizant of the future.
In 2001, the 10 highest-paid players on the Cowboys' roster are scheduled to count $35.8 million against the salary cap, which is expected to increase to $67 million next season.
The Cowboys will also have at least $8 million counting against their cap from players no longer with the team, leaving owner Jerry Jones about $23 million to sign the 40 players needed to fill out his roster.
Clearly, the Cowboys will also have to restructure several contracts this off-season to create additional salary-cap room, because those figures will increase if Alonzo Spellman and McNeil to more palatable contracts as well as whether to retain Dexter Coakley, Leon Lett and James McKnight, who will be unrestricted free agents.
"It will be challenging," Stephen Jones said of managing next season's salary cap. "We have some theoretical ideas about how we're going to get there, but so much depends on how people play from one year to the next.
"We're not going to be in a situation like Buffalo or San Francisco where you're cutting players that you normally wouldn't."
Before the 1999 season, the 49ers released several starters, because they had to create room under the salary cap. This off-season, the Bills released Pro Bowl fullback Sam Gash and former stars Bruce Smith, Andre Reed and Thurman Thomas, because they couldn't afford them.
Stephen Jones said the Cowboys have not released a player they wanted keep. One reason is Dallas rarely wavers from its philosophical approach.
They tend to draft linebackers in the first three rounds so they get quality players at low wages, and they use assistant coach Steve Hoffman to find minimum-wage punters and kickers.
For the most part, Dallas uses free agency to fill small needs. The Cowboys normally don't re-sign linebackers, safeties, kickers or punters. The exception has been strong safety Darren Woodson. Coakley will probably be another exception, because the Cowboys consider him a special player.
If a player doesn't fit their criteria, then the relationship normally ends.
Dallas had questions about Sanders' durability, so Jerry Jones refused to give him the $8 million signing bonus Washington owner Daniel Snyder gave him. And when the Cowboys lost Randall Godfrey, who signed a free-agent contract with Tennessee, they signed solid free-agent veterans, Barron Wortham and Joe Bowden, to replace him.
"Some days it's fun to go to work and some days it's not," Stephen Jones said. "You get frustrated at times, but that's part of the job. We're going to do what we need to do."
The Cowboys always have been good about managing their cap. When the Cowboys give players contracts with huge signing bonuses, the salaries are normally low for the first few seasons. Then the salaries jump dramatically.
At that time, the Cowboys have to decide whether to release the player or restructure his contract to make it more cap friendly. They can do that next season with players such as Larry Allen and Greg Ellis.
It gets a lot trickier with a player like Woodson, who will be 32 entering next season.
Woodson, who will have a $4.8 million cap figure this season, wants to remain in Dallas, but he understands that might not be possible. Dallas might opt for a younger, cheaper player.
"This team is part of my family and I can't see myself wearing another uniform," said Woodson, "but I know how the business works. I might not be here."