How the Cowboys Hedged Their Bet on Dez Bryant with a 'Brilliant' Contract

The Dez Bryant contract is one of the great illusions in sports history. For all the talk from Dallas Cowboys owner Jerry Jones that the team didn't put any safeguards in the deal, it is in fact a series of safeguards built around one main objective: 

Win a Super Bowl now and then hope Bryant can make it through three years.

On face value, the five-year, $70 million deal that Bryant agreed to last Wednesday looks impressive. The $45 million guarantee is the second-most that any wide receiver has ever been promised, trailing only the $48 million figure Calvin Johnson got in 2012 from Detroit.

Like all NFL contracts, the details tell another story—a story that was exemplified by a trip Jones and his son Stephen took to New York on July 14, the day before the deal was formally agreed to. The Joneses flew to New York to meet with executives of Roc Nation, who deal with Bryant's marketing and off-field opportunities.

The meeting was not about the final dollar figures. The Cowboys were already well aware of the five-year, $70 million figure. Those numbers were based directly on a deal the Denver Broncos had offered to wide receiver Demaryius Thomas almost a month before. Two sources aware of the Thomas deal said that the only changes the Broncos made before the pact was announced was to move some money from the later years of the contract to the early years.

While Thomas hadn't agreed to the deal, two sources said that agent Todd France and Denver general manager and executive vice president of football operations John Elway were at an acceptable point in negotiations weeks ago. In the days after reaching that point, France agreed to sell his agency to Creative Artists Association. CAA also employs Tom Condon, Bryant's contract adviser.

At that point, Condon had the working numbers for a Bryant deal. He eventually got the Cowboys to agree to the numbers and even got a slightly larger guarantee for Bryant.

At least theoretically.

In practice, the Joneses were worried, and the contract payouts reflect that.

While Bryant is perhaps the best receiver in the NFL, loves to play and is clearly the best offensive weapon on the Cowboys, he is also high-maintenance and worrisome.

Some of those concerns are relatively benign. He has no sense of time management. Numerous sources have said that Bryant is consistently late to meetings, team buses and other team functions.

Away from the team, he is even less dependable, as explained in the video below.

Beyond the snafus with Jordan Brand (see video above), Bryant has either failed to show up or failed to live up to responsibilities involving three other companies. One of those included a Super Bowl ad shoot in January for Pizza Hut, a Plano, Texas-based company. Bryant was on the way when he canceled at the last minute. Pizza Hut then called quarterback Tony Romo, who took the six-figure deal on short notice. Two sources said Bryant lost anywhere between $400,000 and $1 million in off-field endorsement money.

Aside from his deal with Nike through Jordan Brand, Bryant currently has no other endorsement deals. That's stunning for a player of his caliber on a team with the profile the Cowboys possess.

Four sources have indicated that prior to signing his new contract, Bryant was in financial distress.

That's still only a small part of the Cowboys' concerns. They have been worried about the number of hangers-on that Bryant has living with him. They also continue to be worried about possible recurrences of serious issues, such as the reported violent encounter he had with his mother in July 2012.

Bryant was charged with misdemeanor assault after it was reported that the 911 operator heard his mother say (via a transcription by the Dallas Morning News), "He tried to kill me," and, "He won't go home. I keep telling him to go home. He won't go."

Another incident like that could get Bryant in trouble under the league's personal-conduct policy for domestic violence.

This offseason, as rumors of a videotape showing Bryant in a violent confrontation swirled in the media, Bryant had odd reactions on social media. At one point, he tweeted about being "betrayed," although he didn't explain what that meant and later deleted the tweet.

The bottom line is this: The Joneses were concerned enough with all of this that they went to New York to meet with Roc Nation. The view is that Roc Nation's executives, including founder Jay-Z, are the only ones who can currently get through to Bryant.

To people around the league, the decision to meet Roc Nation was notably abnormal.

"The Cowboys have known Dez for five years," a general manager with another NFL team said. "They know him better than anyone knows him. They know every detail, and they have a relationship with him, yet they still needed assurances. I've been in that situation, but I could have that conversation directly with the player. Not his marketing people."

Meeting with Roc Nation seemed to reassure Jones, as he acknowledged in his conference call with the press after the deal was done:

I must, must emphasize that Roc Nation, Jay-Z—the key people in Roc Nation—did a marvelous job of basically...convincing us and managing Dez and managing him with his off-the-field, with his marketing opportunities, with his finances, that they're an ordinant group that will really make a contribution to Dez. They were very significant in us doing this deal with Dez.

Also, when asked if "there were any safeguards put into the contract to cover yourself in case he has any off-the-field issues" during his conference call, Jones said there was no special language to that effect:

As you know, the league has been addressing conduct policy significantly over the last 18 months. Consequently, we put into any new contracts the things that the league wants in the contract relative to conduct, and Dez has the same thing in his and no more than other veterans we recently signed.

While technically true, Bryant's contract does contain a form of safeguards, particularly early in the deal.

One might assume that collecting the $45 million that is "guaranteed" as part of the five-year, $70 million contract is just a formality for Bryant at this point, but the reality is much different. In truth, the Cowboys did the best job constructing a contract that keeps the money in their control for as long as possible.

For example, Bryant is supposed to get a $20 million signing bonus and a $3 million guaranteed base salary this season. However, $7 million of the signing bonus is deferred until March 15, 2016. Of the remaining $13 million of signing bonus, half has already been paid and the other half will be distributed to Bryant in his weekly game checks this season. 

What the Cowboys have done is basically agreed to pay Bryant $16 million between now and March, a bit at a time. The team was already on the books to pay him $12.8 million under the franchise tag.

"What the Cowboys did is brilliant," said a source familiar with the contract. "They gave Dez an extra [$3.2 million] to get the long-term deal now and make him show up. But if something goes wrong and he defaults on the contract, they still have it. They don't have to go after him. He has to go after them, and that's a lot harder to do if you have other legal problems."

"When you really think about it, what the Cowboys did in this deal tells you a lot about Dez," a general manager from another team said.

Aside from the deferred portion of his signing bonus, the rest of the "guaranteed" money in Bryant's contract is locked up in his base salary for 2016 ($9 million) and 2017 ($13 million).

Again, that's money he may never see if he's not playing.

And the Cowboys have done their best to make sure of it.

Jason Cole covers the NFL for Bleacher Report.