Hoofbite
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Shorter deal favors dak and longer deal favors cowboys. The idea is to spread the guaranteed money over a period of up to 5 years. That's a lot better than 4 years. Imo, Stephen is doing the right thing by wanting a 5 year deal. He has more than one player to consider.
Ideally, the guaranteed amount wouldn't be the same between 4 or 5 year contracts. It's hard to imagine Dak will get an equal or greater amount of money to prorate on a 4-year deal instead of a 5-year deal. It's all proportional. Even if he ends up sucking, you designate him a June 1st cut after year 3 and prorate the remaining cap hits of his 4-year deal over years 4 and 5. That gives you a lesser total guaranteed amount over the same 5-year period. If the team can't decide he's worth the money or not after 7 total seasons, we need some new leadership.
If the team doesn't make a deal, they're losing, IMO. Tagging a 2nd time and then trying to sign him long-term is what will cost the most. $69M guaranteed for 2020 and 2021, and then how much guaranteed after that? Total guarantees after a 2nd tag and subsequent contract, and you've basically paid the same amount as signing him now and guaranteeing all of it in a worst-case scenario. Only difference is, you're also going to take more cap hits if you have to cut him before the contract signed 2-years from now expires. Time is the key, and prices always go up. They could be close to, or halfway over, all the guarantees on a 4-year deal with nearly $70M guaranteed just by signing him to a 4-year deal right now.
Dallas is stupid to play the franchise tag game. He's worth or he isn't. Make a decision and live with it.