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Drew Bledsoe & Maura Bledsoe – Oregon, Estimated $6.5 Million
Drew Bledsoe played 14 seasons in the NFL before taking retirement in 2007. An injury forced him to sit on the benches while Tom Brady hogged the limelight and took his job. He played for the Buffalo Bills and the Dallas Cowboys, and in 2011, he was inducted into the Hall Of Fame. At present, along with wife Maura, they live in Bend, Oregon. However, they are trying to sell their huge 15,000-square-foot house for $6.5 million now. He also co-owns Doubleback Winery, and it is likely that he will never have to face bankruptcy even if he runs out of his NFL money.
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