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Trump contributed $50,000 to former White House chief-of-staff Rahm Emanuel in the recent Chicago mayoral election contest, ahead of the implementation of regulations that change the amount an individual is permitted to contribute to a state or municipal candidate from an unlimited amount to a cap of $5,000 per candidate. Trump also employs Rahm Emanuel's brother, Avi Emanuel, as an agent.

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"The Democratic recipients of Trump's donations make up what looks like a Republican enemies list, including former senator Hillary Rodham Clinton (N.Y.), Sen. John F. Kerry (Mass.), Rep. Charles B. Rangel (N.Y.), Sen. Charles E. Schumer (N.Y.), and the late liberal lion Edward M. Kennedy (Mass.)," wrote Washington Post reporters Dan Eggen and T. W. Farnam in an April article documenting Democrat favoritism in Trump's political donation history. Eggen and Farnam documented that the biggest recipient of Trump political contributions has been the Democratic Senate Campaign Committee of New York, which has taken in more than $125,000 from Trump and his companies. "Overall, Trump has given nearly $600,000 to New York state campaigns, with more than two-thirds going to Democrats," the Washington Post reporters noted.