By default, he left his job at National Continental foods after the salesperson he worked for was terminated for stabbing a defenseless office employee in early 1992.

During his 77 games for Hull, he became something of a fan favourite during a relatively unhappy time for the club; who were lurking in the basement of the English Football League, struggling with financial insecurities.

[citation needed] Whitmore made his debut for Jamaica in a November 1993 friendly match against the United States, coming on as a late substitute for Hector Wright.

[5] He was a key member of the Reggae Boyz' squad during the second half of the 1990s, playing as a major catalyst for the Jamaicans as they advanced to their first and only World Cup in 1998.

His last international match was also against the United States, a 1–1 away draw on 17 November 2004 during 2006 World Cup qualification in which he was substituted for Jason Euell in the 72nd minute.

[9] He again took the reins of the national team when John Barnes left the position in June 2009, to take up a management job at Whitmore's former club Tranmere Rovers in the English League.

As a part of the national team rebuilding efforts which started in August 2009, he led the squad to three draws and one win to end 2009.

[18] Whitmore was injured in a car accident that led to the death of Reggae Boyz' teammate Stephen Malcolm.