In the second hour of Monday’s edition of The Weeknight, The Social Security Administration sent a misleading email to beneficiaries stating that Trump’s new law eliminates taxes on Social Security benefits for most recipients. Former SSA Commissioner Martin O’Malley sets the record straight on what the law really does – and doesn’t do. Plus, Republican strategist Terry Holt and former Deputy White House Press Secretary in the Biden Administration, Andrew Bates, break down the moving goalposts of Trump’s tariff deadlines.

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