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The Cowboys do take risks, just not the kind we want to see
Tim Heitman-USA TODAY Sports

Just short of a week away from the start of NFL , the find their roster full of holes.

This is also the time of year when Cowboys fans get their hopes up for the big names on the market somehow making it to Arlington.

In fact, some of you reading this actually believe the team will take the field in 2024 with at , Justin Simmons at , and Leonard Williams at .

Ahhhh… ' southern drawl got you again, huh?

Those aren't the moves the Cowboys make. They throw all their energy into the draft while the first two, and sometimes three, waves of free agency pass by.

Then come the bargain bin signings. Jerry and load Cowboys fans in the car and take us to the nearest thrift store where we each get to pick one broken toy that's supposed to last us all season.

While is in a tizzy, they will make a public statement about how “all-in” they are except the explanation sounds more like they are trying to convince themselves the words coming out of their mouths are true.

C'mon, do something. Throw the checkbook at the best player in free agency in a position of need and see what happens.

Take some risks for Christ's sake! What if I told you the Cowboys do take risks, just not the kind of risks we want to see?

They only take risks in the draft, and those risks are character concerns or history, and it rarely works out.

Let's take a look at some notable “risks” the Cowboys have taken in the draft, and how each risk paid off (or not). You'll also notice a pattern.

DE Sam Williams

was drafted with the 56th overall pick in the from the University of Mississippi, more affectionately known as Ole Miss.

At Ole Miss, Williams was suspended before the while under investigation for sexual battery. The charges were dropped, but we all know that doesn't equate to innocence.

He relatively stayed out of the unwanted spotlight until the 2022 but his reputation was already tainted, pushing him out of 1st round consideration.

The Cowboys gladly selected him in the 2nd round, deciding that the risk of his trouble with the law did not outweigh the potential success on the field.

Williams was quickly back in the negative spotlight in December of 2022 when he was arrested in Frisco for reckless driving.

Reports say he was driving 98 mph in a 55 mph zone, and eventually caused an accident with one other car.

He would again be in the DFW headlines during the 2023 after being charged with possession of a controlled substance as well as weapons charges.

Williams has produced just 8.5 sacks in two seasons and has issues with his discipline on the field as well as off of it.

So far, the production has not been worth the risk. Here is a list of players the Cowboys passed on in favor of Williams:

  • LB Troy Andersen (Atlanta)
  • CB Cam Taylor-Britt (Cincinnati)
  • S Bryan Cook (Kansas City)
  • C Luke Fortner (Jacksonville)
  • LB Brian Asamoah (Minnesota)

CB Kelvin Joseph

Here is another player with character concerns, and another 2nd round pick where the Cowboys chose to place their one token of risk per season.

Kelvin “Bossman Fat” Joseph was drafted by the Cowboys in the 2nd round of the .

It was the first draft with as , and it showed with eight of the 11 picks coming on the defensive side of the ball.

Joseph ended up being a terrible pick, but the magnitude of the pick is overshadowed by the success of the rest of the draft.

, , , , and all still contribute heavily to the team.

On top of not being as experienced as other cornerbacks in the draft, Joseph was a self-proclaimed rapper with character concerns of his own.

Dallas drafted Joseph from the University of Kentucky but he originally was enrolled with the .

He was suspended by the team in 2019 for violating team rules and eventually transferred to Kentucky.

Dallas finally gave up on Joseph moving into the rotation and traded him away to Miami for their struggling CB Noah Igbinoghene.

Here are some players in the same range that the Cowboys passed on when they selected Joseph with the 44th overall pick:

  • CB Asante Samuel Jr. ()
  • WR Rondale Moore (Arizona)
  • LB Jeremiah Owusu-Koramoah (Cleveland)
  • LB Nick Bolton (Kansas City)
  • LB Pete Werner (New Orleans)
  • C Creed Humphrey (Kansas City)

LB Jaylon Smith

It seems the Cowboys have been looking for that decade-long player at for the past decade.

They thought LB from the University of Notre Dame was the answer, selecting him with the 34th overall pick in the 2016 NFL Draft.

Smith, unlike the previous two players mentioned in this article, did not have character concerns.

His concerns were a devastating injury suffered in the final game of his college career in the Fiesta Bowl versus Ohio State.

Smith tore his ACL and MCL on the fateful play, spoiling the original draft projection of possibly being taken in the top-five overall.

Dallas took the risk when he fell to the 2nd round, confident that the team surgeon would be able to successfully “fix” Smith and bring him close to his previous form.

After recovering from a case of drop-foot, Smith actually had a nice career in Dallas, even earning a second contract that most believed was an overpay.

Smith finished his Cowboys' career with 498 tackles, 9.0 sacks, and two interceptions before spending time in New York, Green Bay, and Las Vegas.

I suppose his Cowboys' career can be deemed a success, but here are some more impactful players Dallas passed on in favor of him:

  • LB Myles Jack (Jacksonville)
  • DT (Kansas City)
  • CB Xavien Howard (Miami)
  • WR Michael Thomas (New Orleans)
  • LB Deion Jones (Atlanta)

DE Randy Gregory

Let's end the article with a player who many feel could have been an all-time great if he could have just kept on the straight and narrow.

was another 2nd round pick of the Cowboys, this time the 60th overall pick in the 2015 NFL Draft from the University of Nebraska.

Gregory's main character concerns were his heavy use of marijuana in college which got him into trouble a handful of times.

The former Cornhusker was too talented for the Cowboys to pass up, however, and he was the pick at 60.

In hindsight, despite the talent, Gregory has to be considered as a failure of a pick, and the risk did not reward as expected.

He missed more games (54) than he played in (38) between 2015 and his eventual release after the 2021 season, including being suspended for two full seasons (2017 and 2019) for repeated violations of the NFL's policy on substance abuse.

Gregory might be the most talented player the Cowboys have taken a risk on so I suppose the risk was worth it, but here are some players Dallas passed on in favor of him:

  • OG Ali Marpet (Tampa Bay)
  • DE Frank Clark (Seattle)
  • WR Tyler Lockett (Seattle)
  • RB David Johnson (Arizona)
  • DE Danielle Hunter (Minnesota)

This article first appeared on Inside The Star and was syndicated with permission.

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