No doubt. I think other GMs did, too, but they were prepared to overpay bigly.
In hindsight, I bet some teams wished they'd have offered more QOs or tried to lock up their QO players a year or two ago, even if just to trade them once the market shot up.
Nobody, here, liked the $30M for one more year initial offer to Bogey. That was very similar to Lester, and again, they did not seem to be willing to quickly follow up with another one. I truly believe they just did not want Bogey back at what everyone perceived the market prices were or would be. Even if he'd have taken $170M/6 a year or year and a half ago, I'm not sure they think he was worth that, then. Hell, they may not have really wanted to pay them that now that market prices have risen.
They signed Story last year. Many saw te writing on the wall, then.
They met with Bogey and then immediately signed Yoshida. They knew they never pay market price at every point through the market price changes.
Call them stupid for undervaluing Bogey, but IMO, they knew exactly what they were doing and were not "stupid" for not offering what it would take to sign him earlier. They don't think he's worth it. They did not think DLowe was. They did not think Pedro was. They did not think Beltre, Damon Betts and others were either.
They have their system for projecting value of their current players and they seem to stick with it. Some examples of getting sentimental and extending players that were nearing or past prime have not always worked out well:
Schilling
Lowell
Youk
Pearce
Nate did fine but not great ('19-'22)
I'm sure I'm missing others and some that worked out well, too.