Winfield is one of the most respected and versatile motivational speakers on the circuit, addressing audiences from colleges to corporations such as American Express, MasterCard, Monster.com, Xerox, IBM, GE Small Business Solutions, General Motors, Bank of America and the FDIC.

He is currently Executive Vice President/Senior Advisor for the San Diego Padres, a studio analyst for ESPN's Baseball Tonight, and a host of the Baseball Music Project.