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Is the Cowboys’ front office setting their players up to fail?

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The list of frustrations grows with each passing year. Each year that passes without a Super Bowl victory. Each year without a conference championship. When yet another season ends in the divisional or wildcard round, or even in missing the playoffs altogether, the frustration grows more.

We all know the numbers by heart. hasn’t won a divisional-round game since the 1995 season.

So, no NFC Championship or Super Bowl appearances since then either.

The Cowboys’ record in regular season games since that year is 244-207. The team has won nine NFC East titles in that span. Twice they were the top seed in the NFC when the playoffs began.

Their playoff record since that last Super Bowl season is just 5-13 – all five wins coming in the wildcard round.

Frustration. Twenty-eight seasons of frustration.

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For the fan base, the frustration, and the years of coming up short, are becoming unbearable.

The assumption is that the frustration is a burden shared by the players and coaches, past and present, as well as everyone associated with the franchise.

But is it, really?

Self-sabotage at The Star?

Self-sabotage. As a noun, it means the sabotaging, whether consciously or subconsciously, of oneself.

As a verb: To sabotage oneself or one’s own plans.

We’ve brought up in the past that despite protestations to the contrary, doesn’t really want to win another title.

He already has the most valuable franchise in the NFL. There’s not much more he needs to do to keep the money flowing in.

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As he already has three Lombardi trophies won under his watch, he’s not fully motivated to win another.

That’s where the “subconscious” self-sabotage enters the discussion.

The rub is, the sabotage that is keeping the Cowboys far from another championship might just be found in the team’s front office.

Too Many Wrong Moves in Dallas

Most General Managers try to put their team and its players in the best possible position to succeed. More often than not that hasn’t been the case in Dallas.

The last three decades have been littered with questionable moves.

Trades that never really paid off. Contracts that did not bring a return on the investment, including some that should never have been offered in the first place.

And then there are the drafts.

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Let’s be clear: The Dallas Cowboys have made solid draft picks, especially in recent years. There have even been some great finds among the undrafted free agents.

Dallas has also made some solid trades for players and for draft picks that have paid off. Last year alone they acquired cornerback Stephon Gilmore and receiver Brandin Cooks via trades.

A few years back they made a big move to land a receiver by getting Amari Cooper from the Raiders. Then they traded Cooper away to Cleveland for next to nothing.

That after signing Michael Gallup to an extension despite coming off a leg injury.

Cooper had a great year for the Browns.

Gallup is no longer on the roster.

Self-sabotage.

Cowboys WR Brandin Cooks

The signing and drafting of players with big injury issues is a pattern with Jerry Jones and the Dallas Cowboys.

Terence Steele has a chance to make such a gamble pay off. Too many others haven’t. Jaylon Smith is another example. He was drafted in the second round, despite the team knowing he would not play in his rookie season.

He was released midway through his fifth season. So that gamble paid off, at least for a little while.

Last year, Luke Schoonmaker was drafted in the second round despite Dallas knowing he had plantar fasciitis. The jury is still out on Schoonmaker’s future.

Putting Players In Bad Positions

The Cowboys’ approach has not been all that helpful. Especially over the last two drafts. Needing to shore up the offensive line in 2023, the Cowboys drafted Mazi Smith on the defensive line.

They turned him into an oversized linebacker, then took Schoonmaker in the next round instead of an offensive lineman.

The offensive line really could have used the help in 2023.

This spring, Dallas finally addressed the offensive line with first-round pick Tyler Guyton.

The Cowboys needed to address the running back position after the departure of Tony Pollard. Instead, they reached for an unneeded defensive lineman in the second round.

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They failed to draft a running back at all. Now they’re stuck hoping that Ezekiel Elliott can revert to his 2016-2019 form.

In short, the Cowboys front office has set this team up to fail.

Refusing to seriously address positions of need in the draft or free agency is the primary reason why the Cowboys fail in the postseason.

They have quality players on the roster, but they leave too many holes, and playoff-quality teams keep exploiting those weaknesses.

The Cowboys front office has no one else to blame for that but themselves.

Consciously or subconsciously, they are sabotaging themselves, and their players, every year.

Richard Paolinelli

Staff Writer

Richard Paolinelli is a sports journalist and author. In addition to his work at InsideTheStar.com, he has a Substack -- Dispatches From A SciFi Scribe – where he discusses numerous topics, including sports in general. He started his newspaper career in 1991 with the Gallup (NM) Independent before going to the Modesto (CA) Bee, Gustine (CA) Press-Standard, and Turlock (CA) Journal -- where he won the 2001 Best Sports Story, in the annual California Newspaper Publishers Association’s Better Newspapers Contest. He then moved to the Merced (CA) Sun-Star, Tracy (CA) Press, Patch and finished his career in 2011 with the San Francisco (CA) Examiner. He has written two Non-Fiction sports books, 11 novels, and has over 30 published short stories.

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