After playing for St. Raymond High School for Boys in his hometown Bronx, New York, he committed to Drexel University for 2004 over interest from other Division I (NCAA) colleges Hofstra, Marist and Canisius.

His second professional season was more successful than his first; on a personal level he was a starter and was in the league top 10 in rebounds [8] and blocks whilst on a collective front his team made the playoffs losing to eventual champion Fenerbahçe.

The reigning champion's easy title in the weaker Estonian league after sweeping the playoffs gave Elegar his first career club silverware, along with a place in the All-KML team.

In May 2013 Elegar moved to Puerto Rico to join the Cangrejeros de Santurce of the Baloncesto Superior Nacional as a replacement for the injured Leon Williams.

In the same season he had his first taste of European competition in the second tier EuroCup where he was a good but unspectacular performer in an unsuccessful campaign, the Estonians finishing 5th in their group of 6 teams.

The next summer he put an end to his journeyman ways, signing a one extension to his contract, which proved to be shrewd business for Kalev as Elegar had an exceptional[clarification needed] season, forming a deadly pick and roll partnership with newly arrived playmaker Scott Machado whose assists helped him reach double digit scoring figures for the second season in a row in the VTB United League and also in the BBL.

This earned the Virgin Islanders a place in the 2007 Pan American Games where, after two close defeats including a rematch against Puerto Rico, they won against the higher ranked Canada.

The pinnacle of Elegar's international career was his participation in the 2007 FIBA Americas Championship, the continent's best tournament where he played against birth nation United States that had in their squad a plethora of NBA champions and All-Stars including LeBron James, Kobe Bryant and Jason Kidd, the game was a blowout as the U.S. Virgin Islands lost 59–123 with Elegar scoring a solitary point in 20 minutes.