So how is it that the Yankees can afford all these things and the Bosox can't? Do the Yankees field a good team year after year because they have more money? Or do they have more money because they field a good team year after year?
The Yankees big source of income is the YES Network. It pulls in tens of millions of dollars due to the NY metro market. It is a huge advantage over other teams. They can go out and trade for overpriced players or sign expensive free agents and not have to worry about rolling a turkey like most any other franchise out there.
Outside of this 5 game debacle over the past 5 years these two teams are extremely close in wins and losses so there is nothing for Yankee fans to walk around with their chests pushed out over. From a ten year period in the mid eighties to the mid-nineties, the Sox had more postseason visits than the Yankees did. After that the Yanks had a great run no doubt but a lot of that was due to pitching, home grown talent and baseball players like Martinez, Knobloch, O'Neil, etc rather than expensive trades and free agent signings.
Previous to that the Sox have had bad ownership that made decisions not to sign both Jackie Robinson and Willie Mays because of Yawkey's racism, they pissed away the core of a good team in the mid-late seventies with stupid moves and bad business operations. (How in the hell do you lose Carlton Fisk because you didn't mail the contract in time???)