Massive dynasty leagues have become increasingly popular among fantasy baseball players in the past half decade. They tend to involve much larger rosters than standard rotisserie leagues and may or may not utilize a contract system that impacts the amount of time an person can own rights to a player.
The most-difficult question a fantasy owner must address in a dynasty league, though, does not take place on draft day. Most of the time, the mind-numbing conundrum occurs midseason when an owner must decide whether or not his or her team will buy, sell, or hold. It’s not a simple question to address, as rebuilding in a larger dynasty league isn’t generally a one-and-done deal. Those rebuilding jobs literally take two or three seasons, at the very least. Embarking on such a strategy isn’t fun, nor is it easy to do well.
As someone who is currently undergoing a massive rebuild in a 20-team dynasty league with 40-man rosters and 35 keepers per year, I wanted to offer a few pieces of advice to owners who have decided they want to sell.