3 Worst Cowboys Contracts to Overcome This Offseason

October 8, 2023; Santa Clara, California, USA; Dallas Cowboys wide receiver Michael Gallup (13)
October 8, 2023; Santa Clara, California, USA; Dallas Cowboys wide receiver Michael Gallup (13) / Kyle Terada-USA TODAY Sports
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The Dallas Cowboys are staring down a couple of really tricky offseasons. This is a win-now roster, but with plenty of key players on expiring deals. Keeping enough talent in Dallas to continue contending will not be cheap.

Of course, then there's the added little wrinkle of a potential Dak Prescott contract extension. That's not going to be cheap either, and it'll completely transform the Cowboys' salary cap situation.

With all of that going on, these three Cowboys' contracts suddenly look a lot more egregious while they hold the franchise back.

1. Michael Gallup

Michael Gallup's inability to contribute even as a WR3 while defenses are forced to key on CeeDee Lamb and Brandin Cooks proves he's just not going to be a valuable contributor at any point.

And boy is he expensive for someone who isn't going to contribute. He carries a $13.9 million cap hit for 2024, and that climbs to $15.8 million for each of the next two years.

Those dollar values aren't the worst of it though. The Cowboys will take on $13 million of dead money if they get rid of Gallup this offseason.

He may well be released as a post-June 1 cut to free up $9.5 million in cap space, but that move would still leave Gallup costing $8.7 million against the cap in 2025. This contract is going to be a nagging pain in Dallas for at least two more years.