Keenan made his collegiate debut on November 5, 2005 against Princeton University at Baker Rink. He scored his first collegiate goal against St. Lawrence University on November 4, 2006 against Alex Petizian at the Bright Arena. Keenan was hampered by numerous injuries in college. He was a college roommate of professional soccer player Mike Fucito.
Professional career
After a short stint playing for the Turnhout White Caps of the Dutch Eredivisie, Keenan signed with EHC Neuwied of the German Oberliga for the remainder of the 2009-10 season. He tallied 15 goals and 14 assists in 14 games played. Keenan began the pre-season playing with Kiekko-Laser in the Finnish Mestis. On September 11, 2010, he signed a contract with Lindlövens IF of the Swedish Division 1. He went on to record 8 goals and 2 assists in 32 games. On August 13, 2011 Keenan reportedly signed a one-year contract with Kramfors-Alliansen of Hockeyettan. It was also rumored he had agreed on a contract with HC Vita Hästen. On October 19, 2011 in a game against Östersunds IK, Keenan delivered a check to current Frölunda HC defenseman Emil Djuse. Keenan was suspended five games for an illegal check to the head. Playing alongside former HockeyAllsvenskan forward Johan Chang, Keenan produced 22 goals, 28 assists for 50 points while racking up 117 penalty minutes in 32 games while Chang piled up 28 goals and 37 assists for 65 points in 40 games. Keenan finished second among North Americans in league scoring behind Andrew Fournier. Teammate and fellow American Dean Moore finished first among defenseman in scoring. Keenan also finished second among North Americans in penalty minutes. Following the season, Kramfors-Alliansen transferred both Keenan and Moore's rights to IF Sundsvall of HockeyAllsvenskan before signing forward Mike Danton to a one-year contract.
Career statistics
Writing
Keenan's first book, , was published by Skyhorse Publishing in January 2016. Vanity Fair published an excerpt from the book in December 2015 calling it "an uproarious new memoir." The Boston Globe reviewed the book, saying "Odd Man Rush is a unique item on the bookshelf...Keenan understands the culture and captures it well." The Buffalo News called it "Ball Four meets hockey." The New York Post called it "a bawdy, often comical chronicle of hockey and survival in far-flung places...the international version of the movie Slap Shot." SB Nation reviewed it, stating "Make no mistake. This is a funny book, but Keenan also has a gift for writing from a place of vulnerability...That being said, you will still find yourself smirking your way through most of Keenan's story." Academy Award-nominated producer Howard Baldwin acquired the film rights to Odd Man Rush, and the project was reported to be in production in February 2019. The Athletic reported the film was in post-production in August 2019 with Creative Artists Agency representing the movie's distribution rights. Post Hill Press acquired the rights to Keenan's second book, a memoir about life as a junior investment banker, with publication scheduled for 2020. His writing has been featured in Vanity Fair, The Huffington Post, Sports Illustrated, and Yahoo! Sports. He is also a frequent contributor to Stan Fischler's The Fischler Report. His resignation email from Deutsche Bankwent viral and was published by Dealbreaker.