When I got my MBA, I did take a negotiations class. I can't really speak to the exact best way to conduct a baseball contract negotiation, as I have never experienced that, but in general, the goal of a good negotiator is to come up with a deal that both sides can accept happily. Obviously, it is unlikely that both parties will get every single thing that they want, but reasonable people wouldn't expect that to happen. Many people think that you are supposed to try to destroy the other party in a negotiation, to get everything and give nothing. That's just not a good negotiation. If you play hardball too much and eventually "win" by getting just about everything you want without leaving anything for the other party, it is unlikely you will get any more business from them. Now, things may be different in pro sports, as, with few exceptions, it seems like teams have no choice but to negotiate with the shark agents like Boras when trying to sign an elite player, regardless of how cutthroat that agent has been in the past. As for "lowballing," it doesn't make sense to make an unrealistically low offer to start, but it also doesn't make sense to put all your cards on the table at the start, either. As long as the offer is reasonable (and $20 million per, while it might be a little low, is still reasonable in CC's case), it won't insult anybody. The Brewers don't know with 100% certainty that CC will want tons more than their first offer, especially if other aspects of the contract are attractive to him. There's no point in offering $25 million per year if he might be willing to take $20 or $22 million per year.