MacCracken graduated from Hawken School, where he captained the football and baseball teams, and became an undergraduate at Hamilton College. During his junior year, he went off campus to do an internship at the White House. While in Washington, MacCracken also found work as an intern with the Washington Redskins. After Hamilton, MacCracken continued his work with the Redskins while receiving his J.D. at Duke Law School. He also spent a summer working for the NFL Management Council, which represents ownership in the Collective Bargaining Agreement. Upon graduation from law school in 1999, MacCracken joined the Cleveland Browns for their first season as an expansion team. He spent eleven years with the Cleveland Browns, where he was in charge of managing the salary cap and the team's chief contract negotiator. He was hired by the Kansas City Chiefs in 2010.
- "Front Office and Staff". KCChiefs.com. Retrieved February 27, 2010.
- "CLARK NAMED STRENGTH COACH, MacCRACKEN HIRED AS DIR. OF FB ADMINISTRATION". KCChiefs.com. 2010-02-25. Archived from the original on 2010-12-11. Retrieved 2010-12-11.
- Florio, Mike (February 25, 2010). "Chiefs hire Trip MacCracken, Mike Clark". ProFootballTalk.com. Retrieved February 27, 2010.