The Dallas Cowboys have been out here treating the offseason like a clearance sale at Bass Pro Shops—snatching up anyone who might fit the roster. They brought in Joe Milton III to cook behind Dak, re-upped guys like Osa and Turpin, and basically said, “If you can ball, saddle up.” It’s giving major “stack the deck before the storm” energy in Dallas. Amidst these strategic acquisitions, another addition is turning heads in Dallas.

We are talking about the veteran OL Saahdiq Charles. You know how some guys just refuse to stay out of the fight? That’s 25-year-old OL Charles for you. One minute he’s showing promise in Washington, the next he’s on the sideline nursing something, and before you know it—bam—he’s calling it quits mid-camp with the Titans. But guess what? Dude’s back like he never left. And who’s going to sign him?

Yeah, you guessed that right. A few days ago, the NFL Network’s Mike Garafolo reported that the Cowboys worked out Charles as he came out of retirement last month. And that’s where it got pretty interesting. On Thursday, Garafolo confirmed the news on his official ‘X’ handle that, “The #Cowboys are signing veteran OL Saahdiq Charles, source says.” Guess the guy looked at the Cowboys’ O-line situation and agreed to come back in action.

Charles’ football career has been anything but smooth. And we aren’t just talking about his NFL career. The guy’s just 25-year-old and could have a memorable career had he not been in the limelight for his character concerns. During his time at Louisiana State as an undergraduate, he was suspended for violating team rules.

Though he did make a comeback and played alongside the likes of Joe Burrow, Ja’Marr Chase, and Justin Jefferson, but his suspension played a crucial role sliding him in the draft. The Washington Redskins drafted Charles in the fourth-round with 108th overall pick, and since then, the guy’s been tackling ups and downs of his career.

He spent his first four seasons in Washington but found himself  in free agency in the last season. Titans did sign him on a one-year $1.5 million deal, but the guy threw a curveball in the mid-season when he announced his retirement. Fast forward to now, and you can just say the 25-year-old OL realized that he still got some juice left.

After the Titans released him, Charles was surely looking for an opportunity. Enter Brian Schottenheimer and the Cowboys… there you go, the guy’s all set to re-start his NFL career. In a new city. With a new team. That said, the Cowboys are finally adding some key players on their roster, but keeping the old players? That’s the tricky part. Courtesy? It’s the Cowboys’ owner again, Jerry Jones.

Jerry Jones just isn’t helping the Cowboys

If there’s one good thing that the Cowboys are arguably the best at, then it’s surely at drafting the right players. Like they kinda turn into that one friend who always picks the right fantasy player before you can click “draft.” From Micah Parsons to CeeDee Lamb and even Dak back in the fourth round—Dallas has had some absolute steals. But keeping the right players on the roster? Well, that’s the tricky part that often puts Jerry Jones under scrutiny.

And that’s where the Fox Sports gambling analyst Jason McIntyre comes in. See, McIntyre first appreciated how well the Cowboys are in the NFL draft. “Folks, the Cowboys in the last five or six years have drafted so well,” he said on The Herd Live. “In the middle rounds, when you’re kind of sort of throwing darts, they got (DeMarvion) Overshown in the third round. He has been a home run, I know he’s injured, but he was great. DeRon Bland, fifth-round pick. You look back a little further, their center, Tony Pollard, Dalton Schultz, those two guys have moved on, but they’ve drafted really well.” The messy part?

Well, when it comes to keeping players on the team for a longer-time, Jerry Jones just takes a step back. No reason why. But JJ has a knack for making headlines with his hands-on approach. And that’s the main concern for McIntyre. “You’re like, ‘damn, you’re great at drafting.’ But then you look around and Tony Pollard’s gone. And Dalton Schultz is gone,” he continued.

That’s the disconnect McIntyre can’t ignore. The Cowboys have proven they can scout with the best of them, unearthing Pro Bowlers deep into the draft. But at some point, the roster starts to fray. Not because of talent evaluation, but because of what happens after. “And all of a sudden you start looking around that roster and it’s like, we’re getting kind of old. We’re losing some players,” McIntyre said. “Jerry’s negotiating tactics, not great with Dak, not great with CeeDee. Certainly not great with Micah Parsons.” The Cowboys aren’t short on stars. The question, as always with Jerry Jones, is whether they can keep enough of them long enough to matter.