Former boston red sox pitcher tim wakefield, beloved for his work on and off the field, has died just days after it was revealed he had been recently diagnosed with brain cancer, according to a. Wakefield won world series titles with the red sox in 2004 and 2007 We are deeply saddened by the loss of tim wakefield, one of the most unique pitchers of his generation and a key part of the most successful era in the history of the boston red sox.