What it is--is my parsimonious yankee blood talking. I was actually born in New England (near Boston), plus both of my parents grew up there. To me $300M is beyond a king's ransom. With it Mookie and his family will want for nothing.
But, if you are an agent, especially Mookie's agent, $300M is just downright insulting in view of Trout's $426M and Mookie's cumulative WAR, which reportedly is second only to Mike's, 2014-19.
That said, however--and this for me (and, I note, for bellhorn) is the real kicker--the risk is entirely on John Henry. If Mookie is a bust or injured or in an accident or whatever, he gets every dime. Mookie gets his hundreds of millions and his agent gets his millions, and John Henry and the Sox fans get what?
And, even if Mookie wins three more MVP's, the Sox pitching could continue to fail--despite the incredible salaries being paid to Price and Sale and even Eovaldi--and the Sox would continue to pay top dollar (overall team salary) with little to show for it in the won/lost columns.
Last year, for example, the great one, Mike Trout, won his 3d MVP (he has also come in 2d in MVP voting 4 times--zowie!), and the LA Angels finished with 72 wins and 90 losses. I seriously doubt that New Englanders--with our presumed yankee parsimonious streak--will stand for that. And why should we?