Chad Ford writes about bad deals:
In many cases, the battle between agent and general manager is not a fair fight. On one side you have the agent, a professional negotiator who spends all year thinking about how to drive up the player's price. On the other side you have GMs, many of whom are former players who have seldom handled negotiations. They usually had agents for that.
Fascinatingly, Ford mentions this and then just lightly moves on. But doesn't it seem like a big deal? It's a business job. Why don't teams hire people with business experience?