I could see his logic, though. He would have been a free agent at age 31, a full three seasons away, and at this point it looks like he's a corner OF instead of a CF which diminishes his value a bit. There was a lot going against him waiting for free agency. He tried to force his way out, which may have gotten him a bigger extension if he were traded to a non-cheap team, but when that ship sailed, he took the guaranteed money/security rather than risk waiting. It's a good deal for the Pirates, and Reynolds at least gets to say he got a $100 million contract.
As much as I would hate to see Nutting rewarded for his cheapness, I hope this is the beginning of a nice run for the Pirates. That fanbase will support a consistent winner and they have one of the best stadiums in the league. Cherington did alright all things considered. He took over a lousy team in 2020, stripped what was left of it down, and by 2023 they are starting to at least look competitive. We will see how long that lasts this season, and what happens in the future.