MacCracken graduated from Hawken School, where he captained the football and baseball teams, and became an undergraduate at Hamilton College.
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.
[3] He joined the Guardians of the newly-formed XFL in 2019 as Director of Player Personnel.