You know how sometimes you're playing Monopoly, and you land on Boardwalk with a hotel, and you go into major debt, and you scramble and sell all your hotels and houses and a bunch of property to pay off that debt, and then you're left with no money and barely any assets that could produce money either? Do you often come back and win after that? No. You do not.
So no, the Times shouldn't sell the Red Sox stake. They'd get $200 million and they'd pour that right down the debt hole and then it would be gone forever, and the company would be in the same bad place, but without one of the few assets they have that is not tanking.
If they hold onto that stake, it will only get more valuable. Besides, the Cubs are already for sale! By Tribune, another newspaper company! And unless a consortium of brain damaged Chicagoans pays about $5 billion for the team, even that sale won't pull Tribune out of bankruptcy. NYT Co. should only sell the baseball stake if they're pulling together cash to go private, which is really really what they should do, but they won't, because Pinch Sulzberger will keep trucking right down the same path he's on now, because he's too proud to take business suggestions from disreputable blogs like this that repeatedly call him "Pinch" and talk about his moose nonstop. Well boo.