Career
He played college basketball for H. Lavity Stoutt Community College and McNeese State. Penn began his career with Tortola"s H. Lavity Stoutt Community College where he averaged a double-double and eight blocked shots during the eight-game season while recording a triple-double in one game. The next season he transferred to McNeese State where on his second year, he led the conference, ranked fourth in the nation and set a single season school record for blocked shots after ending with 117 for an average of 4.0 per game.
By the end of his college career, he was second on the Cowboys" all-time career blocked shots list with 264 career blocked shots.
After going undrafted in the 2009 National Basketball Association draft, Penn was drafted by the Caciques de Humacao with the second selection of Puerto Rico"s 2010 draft and signed afterwards. On August 24, 2011, he returned to Mexico, this time with Fuerza Regia, however, he missed the rest of the 2011–2012 season after suffering a metatarsal fracture.
On March 31, 2012, he returned to Humacao. On July 12, 2012, he moved to Dominican Republic, this time with Huracanes del Atlántico for the rest of the year and on January 18, 2013, he signed with Venezuelan Toros de Aragua.
After a fourth stint with Humacao, Penn was traded on January 21, 2014 to Vaqueros de Bayamón.
After averaging 4.5 points, 5.5 rebounds and 2.0 blocks in 18.4 minutes per game with Vaqueros, Penn signed with the Minnesota Timberwolves on September 18, 2015. On October 24, 2015, he was waived by the Timberwolves after appearing in three preseason games. On December 26, he returned to Venezuela, this time with Trotamundos de Carabobo.
In February 2016, Penn was acquired by Brujos de Guayama.