The Dallas Cowboys are coming off their most successful season in five years, a 12-4 record coupled with a NFC East title, and much of the praise falls on quarterback Tony Romo and his MVP-caliber play.

But Romo’s most potent weapons, NFL-leading rusher DeMarco Murray and the league’s highest scoring receiver Dez Bryant, are scheduled to hit free agency in March.

Now Cowboys owner and general manager Jerry Jones along with his son and team executive vice president Stephen Jones are charged with keeping the team that came within a few plays of reaching the NFC Championship  together with $136 million already devoted to player contracts next season.

The NFL salary cap is expected to reach as high as $141 million next season, roughly three percent higher than the 2014 season, but that leaves Jones with little wiggle room to retain two of his stars.

And Murray and Bryant aren’t the only Cowboys hitting the open market. Dallas could be decimated at right tackle with Doug Free and Jeremy Parnell seeking new deals, and both critical parts of an offensive line that let up only 30 sacks all season and played a huge part in Murray’s breakout year.

The Cowboys could reportedly begin freeing up cap space by restructuring Romo’s six-year, $108 million contract for the second time in as many years, which could work wonders in the short term but the long-term ramifications could leave the team’s cap in dire straits.

According to the Dallas Morning News, the Cowboys could free up $12.8 million in cap space by converting $16 million of Romo’s $17 million salary for next season into a signing a bonus. But that just pushes Romo’s overall cost down the line, and increases his overall cap hit every subsequent year.

Last season, Dallas created $10 million in cap space by flipping $12.5 million of Romo’s salary into a bonus and that increased his cap hit by $2.5 million over the course of the next five seasons, The Morning News reported.

In December, Stephen Jones stated his reservations about tinkering with Romo’s deal again to the Morning News, words Dallas fans might not want to hear.

“Obviously you don’t like to mortgage your future if you can help it,” Jones said. “We started making the move toward being a younger team and going a different direction in terms of pushing money out, so we’d prefer not to do that, but at the same time every situation has ramifications and you have to make tough decisions sometimes.

“I don’t think there’s an exact science, ‘Hey, we’re going to do it or not do it.’”

Essentially, it’s a practice Cowboys fans have become accustomed. It’s the reason Dallas was $25 million over the cap before the start of free agency this time last year, and it played a major role in the somewhat premature release of Cowboys all-time sack leader DeMarcus Ware.

There’s also the question of whether $12.5 million would even be enough to re-acquire both Murray and Bryant. Despite the injuries he struggled with in his first three years in the league, the 26-year-old Murray showed his full repertoire last season with an incredible 1,845 rushing yards and 13 touchdowns and broke the NFL single-season record with eight straight 100-yard rushing games.

The market hasn’t been kind to running backs for the last half decade, but Murray and his representatives are likely seeking a deal similar to Minnesota Vikings back Adrian Peterson, a six-year $86.2 million contract with $36 million guaranteed.

There are at least a few factors in Murray’s favor. For one, he still has a four-year window of prime production before he hits 30, the age many running backs are shuttered out of the league due to wear and tear or diminishing speed and explosiveness.

There are also the current negotiations between running back Marshawn Lynch and the Seattle Seahawks. Lynch is two years older than Murray, but reported before the Super Bowl he could earn a deal worth more than $10 million next season alone.

Jerry Jones is known to reward his players for their previous work, a practice that worked well with tight end Jason Witten but fell flat with former Cowboys running back Marion Barber, who was cut in 2010 after signing a seven-year $45 million deal only two years prior.

However, Bryant’s potential deal could be the most difficult for the Jones family to hurdle. Wide receivers on average earn far more than running backs, and Bryant could hold out for a deal like the one the Detroit Lions gave to superstar Calvin Johnson. In 2013, Johnson signed a record seven-year, $113.4 million extension with the Lions, with $48.7 million guaranteed.

Any potential alternatives to Bryant would still require the Cowboys to free up cap space. Should they let Bryant walk and look for another available receiver on the market, Dallas would still need to create space in order to sign the likes of Denver’s Demaryius Thomas or Philadelphia’s Jeremy Maclin.

Considering his substantial production on the field every year, it will be difficult for the Cowboys not to fold to Bryant’s likely demands. He’s recorded three straight 1,000-yard seasons with a total of 41 touchdowns since 2012, and Bryant seems far removed from the off-field issues that plagued him when he first entered the league in 2010.

The Cowboys front office has a difficult financial battle ahead, but the chance to improve on last year’s improbable season might be too tempting.