Will the Dallas Cowboys gamble with their draft picks again this year?

More Cowboys draft gambles:

2017 – Taco Charlton, defensive end, drafted in the first round, despite a lack of speed, and predictions it might take him a few years to develop.

Result: Charlton might just exceed Gregory as a disappointment, though it’s a close competition.

As a rookie, Charlton didn’t look completely hopeless. He played primarily as a backup, making 19 tackles and three sacks. But he regressed his sophomore season, making only one sack, and there were reports of attitude problems.

He was released before the start of the 2019 season. Charlton is the only Cowboys first-round pick in the last 10 years to be released before his rookie contract expired. He’s definitely a bust.

2018 – Leighton Vander Esch, linebacker, drafted in the first round, despite injury concerns. Vander Esch injured his neck during his junior year and was limited to six games that season.

Result: Vander Esch was outstanding as a rookie, making 140 tackles and two interceptions. He appeared in the Pro Bowl that year, and was in the running for defensive rookie of the year. With such a stellar rookie season, he came into the 2020 season with enormous expectations.

Unfortunately, Vander Esch injured his neck midway through his sophomore season and missed the final six games in 2019. Since then, he’s had surgery to repair the damage.

Though the Cowboys have expressed optimism in his recovery, according to CBS Sports, neck injuries are scary. It’s hard to say how well he’ll play going forward, or how many years he’ll be able to continue in the league.

2018/19 – Amari Cooper, wide receiver. Dallas traded their first-round pick to the (then) Oakland (now Las Vegas) Raiders for Cooper, in the middle of the 2018 season.

Result: Cooper gave the team an immediate lift and was credited with helping the Cowboys make the playoffs that year. The effort earned him his third Pro Bowl berth.

2019 was a little up-and-down for the star wide receiver. Cooper caught passes for eight touchdowns and 1189 yards receiving, but he performed poorly in big games, and in road games.

He’s a free agent now, so it’s possible the Cowboys could receive only a year and a half service for their first-round investment. Still, even if that happens, many observers would call the trade a success, based on Dallas making the playoffs following the trade. As for 2020, stay tuned.

2019 – Trysten Hill, defensive tackle, drafted in the second round, even though he’d been demoted from his starting position on the defensive line of the University of Central Florida due to character concerns. At the time of the draft, Hill had been projected to be drafted in the third round, but Dallas drafted him earlier, at the urging of defensive coaches.

Result: Hill wasn’t even on the game-day roster for most of his rookie season, and only made four tackles. With a new coaching staff on the team, it will be interesting to see how they view Hill, and how they’ll use him.  But so far, he’s been a major disappointment.