Drew Bledsoe – $35 Million

Drew Bledsoe’s NFL career spanned 14 seasons, eight of which he spent as the starting quarterback for the New England Patriots before Tom Brady. Drafted in the early ’90 as the team’s top pick, he played a significant role in turning the franchise’s fortunes around. Injuries shortened his career, but it was still an impressive run that left him worth $35 million.

After retiring in 2007, Bledsoe co-founded the Doubleback Winery with a friend, which has become a successful champagne business venture. He continues to live comfortably off his earnings from football and the winery and spends his spare time doing philanthropy.