We all know the negatives about Pickens, but this can work out for the Cowboys in many ways.
1. This is his contract year. He realizes he needs to be at this best, on and off the field, or else his payday will not come. This means he will do his best to play lights out for the Cowboys, which is great for the team.
2. This is not necessarily a one year rental. Even if Dallas wants to keep him in 2026, the franchise tag remains an option. The cap will only increase and Micah Parsons' deal will be (in theory) done by then. Which, believe it or not, helps the Cowboys create room to keep Pickens.
3. Let's say they don't keep Pickens, which means he played so well in 2025 Dallas can't afford him. That's another win. Let him sign a huge deal elsewhere, and gain a 3rd round comp pick in 2027 as a result. That's two extra picks from this trade in 2027, a comp for Pickens and the 6th Pittsburgh gave up.
Short term and long term, this is a trade that can do nothing but help.