There is only one team, still, in baseball history that spent more than $200 million on baseball players and actually won the Series. That was the 2009 New York Yankees. Their payroll that year was around $210 million. They have spent more than $200 million a year for every year since that (the way they did for the five years before that), and haven't won since. The season before last, they committed seven years to Jacoby Ellsbury and seven years to Masahiro Tanaka and more than $300 million in future financial commitments to the two of them.