From Philly: Wilt Chamberlain, Will Smith, Earl Monroe, Hall and Oates, Bobby Darin, Peter Boyle, Dick Clark, Broderick Crawford, and Larry Fine. And me. Since you mentioned Trump, he went to college there.
Boston: John Adams, John Quincy Adams, Charles Francis Adams, Charles Francis Adams Jr., John Quincy Adams II, Henry Adams, Charles Francis Adams III, Charles Francis Adams IV, and Donna Summer.