Why not some rich guy for mayor?

Kevin wonders: If Mike Bloomberg can buy himself the mayor's office in New York and some rich guy in Philadelphia can announce he'll be spending $5 million of his own money to become mayor, what if some local rich guy ran for mayor of Boston?

... [A] wealthy and charismatic outsider could attract the attention and buzz that Hub mayoral challenger Maura Hennigan was never able to get. Who would be Boston's Bloomberg or Katz, or Schwarzenneger? ...