First, Pickens said he wasn't interested in signing a long term deal. It's not like they could have held him down and forced him to sign a team friendly deal.
I think you may be getting the timeline a little bit muddied or, more likely, simply aren’t recalling the facts
Soon after the trade Pickens was asked about signing an extension before or during the 2025 season. Jerry had already said there weren’t any negotiations but the media had to ask. Pickens said he was jsut going to play ball and let the negotiations play out between the Cowboys and his agent.
The Cowboys publicly shut down any talk of an extension during the season
After the season Jerry came right out of the gate before the combine and publicly said, in his combine bus press conference, that they had informed Pickens that there would be no long term deal and that he was getting the tag.
Pickens only response was basically “it’s whatever, I’m gonna ball and not worry about the tag.
Since then not a word, but of course Jerry and Stephen had to flex right before the draft and restate that they had no intentions to work on a long term deal and that GP would play on the tag. It was out of the blue and not in response to any thing and was just a Jones flex to get media attention
A day or so later there were comments that Pickens had signed the tag (he hadn’t) and then the trade rumors on draft weekend. All of that was almost certainly Jerry and Stephen.
So, there’s zero evidence that GP was playing hard to get or didn’t want to sign. To the contrary, the cowboys played the entire thing out in the media and Pickens gave little or no response,