Sox management doesn’t swing wildly from moneyball to yankeeball. They do both at the same time, all the time. They certainly have extensive resources. Not to the level of Georgie Porgie, but certainly beyond most teams. But they figure to maximize their chances at winning more World Series if they act like Donald Trump using coupons. You swing for the fences, but only when you think it’s a prime opportunity. The Yankees of today are kind of like they were in the 80s and early 90s. The World Series teams of the late 90s were more “moneyball” than they are now.
While it seems excessive to spend $40 mill for the right to negotiate with Matsuzaka, it is as much an investment in developing Japan as a frontier for the Red Sox. The Yankees make tons of money there because they are the Yankees. The Mariners make tons of money there because of Ichiro. The Sox can both sell merchandise there and make the Sox a more desirable location for future Japanese stars. Matsui was a free agent and chose the Yankees more than the biggest contract. The posting system itself (this bidding for negotiating rights) was developed when a pitcher by the name of Hideki Irabu was drafted by the Padres, but refused to sign and forced a trade to the Yankees, where he wanted to go.