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Reflecting on George W. Bush’s failed push for Social Security reform, this episode crunches the numbers on what could have been—a 337% S&P 500 gain since 2006—and examines the political missteps from both parties that derailed it. From Democratic resistance to Republican distractions in Iraq, we explore how fear, partisanship, and short-term thinking kept Americans from building lasting wealth through market-based Social Security investing.