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5 times Cowboys owner Jerry Jones took a gamble on a player

Randy Gregory, the Dallas defensive end who is reportedly facing a suspension and entered a drug treatment facility this week, certainly isn’t the first Cowboys player that Jerry Jones has taken a chance on.

It’s, in fact, one of the Cowboys’ owners top traits — his love of taking chances on players deemed too troubled, injured, facing potential suspensions or even radioactive for other teams. While we still don’t know how Gregory will work out, here’s how some of his latest bets have turned out:

1. Dez Bryant

When Bryant entered the draft, there were a number of questions about him. This from NFL.com:

Before Dez Bryant’s 2012 breakout season and newfound maturity, the Dallas Cowboys were roundly criticized for ignoring a laundry list of red flags trailing the troubled Oklahoma State star. In fact, former Cowboys scout Bryan Broaddus told KRLD-FM last week that Bryant had the worst background of any player he had ever seen coming out of college.

Bryant was raised by a single, often-absentee mother who spent 18 months in prison for selling crack cocaine. He grew up impoverished and without direction, which explains his “lack of life skills” and ignorance of basic adult responsibilities entering the NFL.

For all of the concern over Bryant’s checkered background, he had never run afoul of the law for issues relating to drugs, alcohol or violence. Was he a neglected and undisciplined kid who would thrive with structure and tough love or a bad seed who would end up haunting the Cowboys?

USA TODAY Sports Images

USA TODAY Sports Images

The Cowboys selected him with the 24th pick, and it’s been a pretty resounding success. He’s going into his seventh season with the Cowboys.

2. Greg Hardy

After Hardy was released from the Panthers following his domestic violence conviction (which was later vacated on appeal when the victim couldn’t be located to testify), the Cowboys signed him to a one-year deal. After a year of reports of him being a cancer in the locker room and poor production, he was not re-signed.

3. La’el Collins

Collins fell quickly in the draft after his name was linked to a double homicide. More from NFL.com:

Collins is currently working to clear his name in a Louisiana police investigation into the murder of Brittany Mills. Collins met with Baton Rouge police Monday and is not considered a suspect. Mills, 29, was pregnant at the time of her death and had a previous relationship with the LSU star. Rapoport reported on Wednesday that test results showed Collins is not the father of the baby who died in Baton Rouge, per a source informed of the results. The legal situation delayed Collins’ entry into the NFL.

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USA TODAY Sports Images

He started 11 games for the Cowboys last season.

4. Jaylon Smith

This is an entirely different type of gamble: Smith was considered a surefire top draft pick until he badly injured his knee in Notre Dame’s bowl game. Jones and the Cowboys ignored concerns about the injury and selected him early in the second round of the 2016 draft. While it’s too early to say, here’s how it’s going so far:

But that really doesn’t mean it’s over yet:

5. Terrell Owens

Owens signed with the Cowboys in 2006 after an ugly divorce from the Eagles. More from the AP at the time:

There’s no questioning his talent — Owens has consistently put up statistics the Cowboys have lacked since Michael Irvin was in the prime of his career in the mid-1990s.

It’s his attitude that’s an issue. Owens has badmouthed his last two quarterbacks even though both were Pro Bowl players, squabbled with coaches and gotten angry at his bosses for not properly celebrating personal milestones such as his 100th career touchdown.

“I’m going in with my eyes wide open,” said his newest quarterback, Drew Bledsoe. “I know there have been some issues. But at the same time, going forward from here, I don’t see how it helps us to dwell on some of the stuff that’s gone on in the past.”

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USA TODAY Sports Images

He lasted for three seasons before off-the-field woes reportedly led the Cowboys to let him go in 2009. From an ESPN report then:

Not only did Owens have relationship issues with quarterback Tony Romo and tight end Jason Witten, but the receiver consistently criticized offensive coordinator Jason Garrett’s play calling and his offensive schemes to the point that sources have said Garrett did not believe he and Owens could coexist.

Although the Cowboys were trying to downplay a possible rift between Owens and Witten during the season, the two reportedly came close to blows in mid-December.

An incident occurred at the Cowboys’ training facility when Witten tried to engage Owens in a conversation about a pass route. Owens told Witten to stay away from him and called him a name. The two exchanged words before being separated.

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