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Seems when teams trade for a player, a contract extension is often agreed to right after the trade, but that wasn't *the case with Dee Winters. In your opinion, is this wait-and-see approach with him a pro or con?* – Garet Tanaka/*Wailuku*, HI
Tommy: I would say it's a pro. Winters has yet to play a snap in Dallas, and is on a favorable deal with the Cowboys right now in terms of salary cap. Dallas did the exact same thing with George Pickens last year. This was a trade to add a player with experience to a position that didn't have a lot of bodies in it, and Winters has a chance to earn himself a nice pay day if he has a good year in Dallas.
To my knowledge, I can't remember the last time the Cowboys traded for a player and immediately signed them to an extension at least in recent history. Pickens was a trade, Quinnen Williams was only a trade, Jonathan Mingo was just a trade, and all of the trades the Cowboys made in the offseason last year to add to the roster did not include extensions. The Winters deal seems to fall along those same lines of making 2026 a "prove it" year of sorts, and someone who can elevate the floor of the defense in 2026.
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