Richards was a member of the youth system of Jamaican National Premier League side Seba United while attending Cornwall College in Montego Bay, where he won the DaCosta Cup and Olivier Shield.

One summer, he led the youth soccer camp at Clemson University where he coached the likes of Emmett Lunceford, Robert Sullivan, and John Birnie.

Richards was drafted in the second round of the 2007 MLS SuperDraft by New York Red Bulls, establishing himself as the first team right winger for the club.

In the 2008 MLS Cup Playoffs, Richards helped the Red Bulls to an upset over defending Champion Houston Dynamo (4-1 on aggregate).

[5] Richards concluded his 2010 campaign scoring five goals in his last seven matches helping New York to capture the Eastern Conference regular season title.

On 26 August 2012 it was confirmed that Richards would join English Championship side Burnley on 1 January 2013 after the end of the MLS season and in the European transfer window.

Upon his return from his loan spell, Richards was released from his Burnley contract so that he could permanently join Norwegian side FK Bodø/Glimt.

On 13 April 2014 Richards helped Bodø/Glimt record their first victory of the Tippeligaen season, scoring the equalizer in a 4-2 come from behind win over Sogndal.

[16] On 10 July 2015, the Red Bulls announced that Richards would be loaned out to NASL side Indy Eleven for the remainder of the season.

His play during the 2007 season did not go unnoticed by the Jamaica Football Federation as he was rewarded by being called up to the national team for friendlies against El Salvador and Guatemala in Kingston.

[23] Richards scored three(3) goals for Jamaica in December 2010, leading them to another Caribbean Cup title, while also winning the Golden Boot.