Machado received the most money an athlete ever got in American sports. How much did his attitude hold him back? It's not like he "settled" for 10/$200M. In a depressed (and you can argue the causes of this depression) market, where a lot of big players were out of the running (no Boston, no NY Mets or Dodgers or Angels, and really, the Yankees didn't "need" him) he still got a bunch of cash from a team that hasn't made this big of a free agent acquisition since Bruce Hurst and Jack Clark in 1989.
The Padres were bidding against the White Sox, who again, offered Machado slightly more than he received from San Diego. I'm not sure how he left money on the table.