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The Cowboys offseason approach feels wobbly and leading to a regression

The same old offseason approach hasn’t really worked so far with the Cowboys chaotic offseason.

NFL: NFL Draft-Red Carpet Arrivals Jerome Miron-USA TODAY Sports

The offseason can be a dark place for Cowboys fans. After believing things would be different following a crushing playoff loss to the 49ers, the Cowboys traded Amari Cooper to the Browns. The move gave Dallas some much-needed cap space flexibility, which they began to use in a familiar way.

On Monday, the Cowboys tried-and-true offseason strategy of focusing on internal free agents and preparing a roster that allows them to draft the best players available was in clear view. Michael Gallup was retained on a team-friendly deal, despite having leverage once the team traded Cooper. DeMarcus Lawrence was given a new deal to spread out his cap hit, and solidifying his next few years with the Cowboys. Randy Gregory and the Cowboys were closing in on an agreement, and this Cowboys offseason was starting to feel very familiar.

We can argue all day about whether or not a familiar offseason approach is what the Cowboys need right now or not, but there’s no denying they’ve been consistently good at it. Liking the guys they have and drafting well to infuse young talent has kept them atop the NFC East when the roster is healthy.

A long stint atop a still-weak division is one of the best ways the Cowboys can work towards ending their NFC Championship drought. It’s been 26 years since the Cowboys won the Super Bowl in 1996, a year they won the division for a fourth time in a row. The 90s Cowboys streak would end at five NFC East crowns the following season, and they haven’t repeated as division winners since.

The Cowboys are handling this offseason with some bigger names than usual at the negotiating table across from Jerry and Stephen Jones, and on Tuesday their approach cost them defensive end Randy Gregory. The team’s loyalty to Gregory had finally paid off in 2021, and the two sides were drawing closer to keeping Gregory paired with Lawrence and Micah Parsons in Dan Quinn’s defense. With other teams clearly in waiting for the top pass rusher’s talent, the Denver Broncos took advantage of the Cowboys confusion with Gregory and his agents, and signed Gregory for the same money the Cowboys were offering.

The NFL is different in 2021 than it was in the 1990s, or earlier. If any player could have bought into the team loyalty mantra the Jones’ are still selling, it should have been Gregory. The fact the Cowboys still lost out on one of their most important free agents shows how behind they are with the rest of the league. The Baltimore Ravens, a franchise that didn’t exist when the Cowboys were using this approach to win Super Bowls, have come into the league and won multiple times while Dallas continues to get in their own way.

The Cowboys roster is still as fluid as any team’s can be in mid-March, but two things are true as of right now. They don’t look as good on paper as they were in 2021, when they won 12 games, and they don’t have a clear team strength or identity.

The passing game was supposed to be this team’s overwhelming strength last year, but it disappeared far too many times in the second half of the season and through the playoff loss. Their first big move this offseason was trading a key player away from this strength in Cooper, and they also lost Cedrick Wilson to the Dolphins.

NFL: NFC Wild Card Playoff-San Francisco 49ers at Dallas Cowboys Kevin Jairaj-USA TODAY Sports

Keeping Dak Prescott upright was also a problem in the passing game, and the Cowboys look to be creating more holes than they can fill in one draft up front. Connor Williams was expected to sign elsewhere, which he did on Tuesday with the Dolphins, but La’el Collins’ future with the Cowboys remains uncertain. Losing Collins could be replaced by Terence Steele, but guard and center still are uncertain, and Tyron Smith's health is always an issue.

On defense now without Gregory, defensive end is a glaring need that even the 24th overall pick might do little to fix. Rookie edge defenders rarely make an impact on day one, and the Cowboys would be ignoring some glaring needs on offense to take a pass rusher in need of development first. If Parsons is a big part of the plan to ease the loss of Gregory, then linebacker becomes another need.

There’s also a lack of numbers in the secondary, particularly at safety where Jayron Kearse remains a free agent, to complete the clean sweep of Dallas needing help across the board.

The Cowboys have been building this way for years, but this offseason feels like it’s teetering on an edge. Draft picks that did little as rookies last year now have a path towards earning plenty of snaps, but are we really going to let this team sell us on Chauncey Golston, Josh Ball, or Jabril Cox being the answers on a team expecting to contend?

The Cowboys need to make the rest of this free agency period pay off before the draft arrives if they want to get back to the level the roster was in 2021.

There’s no one thing the Cowboys can hang their hat on right now as something they do better than most teams. In a league where parity rules and a .500 record is the standard, a good way to judge the moves a team makes is predicting how far over this .500 record it might get them. The Cowboys went a perfect 6-0 in division games last year, but might be closer to this average record than we want to admit if a few of those wins are attributed to beating severely overmatched teams. The offseason so far has done nothing but draw them even closer to average.