Many analyses of the White Sox off-season focus on how the optimum strategy for the White Sox is not to collect veterans at the expense of the farm system. This may be true.
But let's realize that the alternative strategy of dump-and-rebuild isn't feasible due to special circumstances. It may never be. Simply put, the White Sox are not allowed to surrender a season in Chicago for rebuilding, as the financial impact would be devastating. The Mariotti types have spent the last thirty years carefully building the canard that Jerry Reinsdorf is a Scrooge who steals fans' money with a second-rate product, and they would go on the warpath about cheap ownership. Rebuilding would throw raw meat to the dog pack. The attendance would drop to 12th or 13th in the league because the average (that is, non-hard-core) paying Chicago customer seems pre-disposed to believe baloney.
Now, Oakland can get away with this because they are moving into a new park in a few years and the counter-buzz from the Fremont move will restore the financial situation, and because the Giants are hardly an alternative fan draw any more. Houston could get away with it because their fans are willing to pay for anything. But the White Sox are trapped. They have to appear to be contending (or desperately trying) in April or May or the balance sheet turns bright red. Trading the expensive players to recoup doesn't work because with the White Sox fan base it takes YEARS of competitive baseball to recover the finances from a "management betrayal".
I think they have to sink naturally, fighting to survive, to keep up appearances.
One of the few bad consequences of the influx of Ivy Leaguers into the baseball analysis world is the loss of the basic truth that MLB is a commercialized amusement, and rebuilding is, well, not amusing. Florida is among the most successful franchises of the last 11 years by the championship metric, but nobody really wants to be them... MLB isn't a classroom game theory exercise. You have to get people to pay to watch teams not called the Red Sox and Yankees and Cubs and Dodgers. Each franchise has its own row to hoe.
And let's talk about the last two times the White Sox went into dump-and-rebuild mode, 1988 and 1997. The first time they had a new stadium -- and four straight jackpot draft choices -- to recover. The second time (the White Flag) they didn't financially recover for almost a decade for a trade that worked out. Dump-and-collect is not viable for the White Sox until the world stops whitewashing every sleazy, greedy trick the Cubs financial wizards do while pretending that the White Sox are run by diabolical misers.