Arena played for the United States Under-20 team at the FIFA World Youth Championship in Argentina in 2001. He was drafted as a Project-40 32nd overall in the 2003 MLS SuperDraft by the MetroStars after a distinguished career at the University of Virginia. After a below average first season with the Metros, when Kenny made a number of key mistakes in limited duty, he came back much stronger in 2004, even scoring a goal with his posterior. He was traded to DC before the 2005 season.