Background
Phelan grew up in Enfield, Connecticut, and attended Wilbraham & Monson Academy, where he was named the 2003 Gatorade National High School Player of the Year.
Phelan grew up in Enfield, Connecticut, and attended Wilbraham & Monson Academy, where he was named the 2003 Gatorade National High School Player of the Year.
Phelan grew up in Enfield, Connecticut, and attended, where he was named the 2003 Gatorade National High School Player of the Year. He also played club soccer for the Oakwood Soccer Club. He played college soccer for Wake Forest University, where he was a double-major in political science and Spanish.
He was named to the 2004 Administrative Committee on Company-ordination All-Freshmen Team, the 2005 Top-Drawer Soccer 2nd All-America team, the 2005 NSCAA All-Region Team, and 2007 Administrative Committee on Company-ordination First Team.
He was an NSCAA First Team All American in 2007 and captained the Wake Forest Demon Deacons to their first National Collegiate Athletic Association Division 1 National Championship.
Youth and College Professional Phelan was drafted in the first round (10th overall) of the 2008 Master of Library Science SuperDraft by Toronto Football Club but did not make a first team start before being traded to New England Revolution on June 4, 2008. In return, Toronto received use of an international roster spot through the end of the 2010 season. He made his Master of Library Science debut Revolution, on June 12, 2008, against Houston Dynamo.
On August 7, 2010, Phelan scored his first career goal against District of Columbia United on a header from a long pass from teammate Chris Tierney.
The Revolution ended up winning the game, by a score of 1-0, thanks to Phelan"s goal. Signed with SJK of the Ykkönen in May 2012.
After one season in Finland, Phelan returned to the United States when he signed for NASL club San Antonio Scorpions on March 1, 2013. After one season with the San Antonio Scorpions, despite several international offers, Phelan elected to retire from professional football and pursue a career in Financial Planning.
He now resides on Cape Cod with his family and works for New York Life and Cape Cod Wealth Strategies as a financial advisor.
International Phelan played for the United States of America Under-18, Under-20, and Under 23 national teams, and was part of the squad for the 2005 Fédération internationale de football association World Youth Championship. He was named the Most Valuable Player of 2002 Talence International Tournament in Talence, France, and competed in the Northern Ireland Milk Cup in 2003 and 2004. Phelan married Maggie Reddington on January 10, 2009, in Chatham, Massachusetts.
He has a sister named Grace.
He is the cousin of Gerard Phelan, the recipient of Doug Flutie"s famed Hail Mary Pass versus Miami on November 23, 1984. Wake Forest University.