Pretty certain the Jake situation went like this; Dubas and Jake's camp met the summer before he was dealt. Jake's camp wanted a huge contract and assurance the team was going to be competitive. Dubas didn't want to commit a colossal deal to a 30 year old with the team on a steep and steady decline. Two sides very far apart in the summer. Talks shelved, Jake's camp feels slighted. No talks during the season. It's public knowledge Jake's camp isn't negotiating in season, whether with Pens or a new team. Jake's dealt, the return is what you'd expect for someone of Jake's caliber but without any indication he's interested in re-signing. Still refuses to talk extension with Carolina. Carolina fizzles out in the playoffs. Talks ramp up and the sides aren't very close. Getting near July and Carolina throws a hail mary 8x8 deal, Jake declines. Carolina trades Jake to Tampa. Jake signs colossal deal, gets to live in a millionaire's life in Florida while playing alongside Kuch and/or Point. End.
There were a bunch of reports that the two sides weren't close, negotiations were at a standstill and not progressing, and Jake's agent publicly saying "this could get very ugly."
Dude left because he wanted to. If he really wanted to be a Penguin, he'd still be here, but there was no reason to take a steep pay cut and wallow in this slopshit organization for the rest of Sid's career before being dealt down the road. He took his colossal deal, ended up with some stellar linemates and on a team gunning for Cups before their window closes.
Worked out for both sides, imo. Anyway, f*** Jake Guentzel. He's a dweeb.