List Of Players That Google Tells Me Are Currently Ahead Of Schedule Returning From Injury:

If you’re dealing with a customer you almost always want to set your deadline/schedule very conservatively. When things go wrong, as they probably will, you’ll still be “on-time.” If things go normally you’re ahead of schedule and the customer is happy.

The construction industry is about the only place I can think of that doesn’t seem to use the method, they’re always behind schedule and way over budget. I suppose that’s because when you have to bidding on a job you have to really sell your service, so of course you’re going to lie about what you can deliver as much as people will accept.

My guess is, it’s almost exclusively the agent, player, or executive who just signed the guy, all of whom have a vested interest in generating excitement about the abilities and worth of the player in the coming year.

Less to do with conservative estimates up front than inflating expectations for the future.