Dwight Yorke was nicknamed 'The Smiling Assassin' due to the fact he was constantly smiling and his goal-scoring abilities. He is still a keen supporter of Aston Villa as he has very fond memories of his time there.
During his time with Aston Villa, from 1989 to 1998, Yorke played initially as a right winger until the 1995-96 season, he then switched to centre forward and quickly established himself as one of the Premiership's top strikers. Yorke was an integral member of the Villa team that reached the League Cup Final in 1996. Villa won 3-0 with Yorke getting on the scoresheet. On September 30 1996 he scored a brilliant hat-trick against Newcastle United in a 4-3 defeat. Newcastle were leading 3-1 at half-time and Aston Villa were down to ten men, with Mark Draper being sent off late in the first half. Yorke showed great character in leading his team in a brave fight back by scoring two more goals in the second half to complete his hat-trick, although it was to no avail as Aston Villa still lost the game. Yorke scored a fourth goal to equalise the game at 4-all, only for his goal to be ruled offside. It was performances like this that led to interest from Manchester United in August 1998. Yorke appeared for Aston Villa on 231 occasions, scoring 97 times. He also has the disctint honour of being the last ever Villa player to score in front of the old Holte End standing terrace, notching both goals in a 2-1 victory on the final day of the 1993-94 season, May 7th 1994.
The circumstances of his departure from Aston Villa were very controversial; Manchester United were accused of making an illegal approach for the player. John Gregory, Aston Villa manager at that time, made it known that the club did not want to sell Yorke to Manchester United unless they were prepared to exchange Andy Cole, a striker at Manchester United. Yorke then approached Gregory to state that he wanted to leave the club, to which Gregory was famously attributed to saying that he would shoot Yorke if he had had a gun in his office. Yorke played in a match for Villa at Everton early in the season in August 1998, however it appeared he made no effort during the match as he was unhappy at not being allowed to leave the club. Aston Villa was left with no option but to sell the player and he was transferred to Manchester United for £12.6 million in August 1998. Despite spending 9 years at Villa he is disliked by some of its fans due to his behaviour at the time he left the club and also due to the fact he later joined Birmingham City, the arch-rivals of Aston Villa, but he is also widely regarded in the hearts of Aston Villa fans as one of the clubs greatest ever goalscorers.
However, in the 2001-02 season, Yorke lost his place in the line-up following the arrival of Ruud van Nistelrooy. It was also rumoured that Yorke had a fall-out with United boss, Sir Alex Ferguson, following his much publicised relationship with British model Jordan. The following summer he was sold to Blackburn Rovers for £2 million.
Altogether he scored 64 goals for Manchester United in 188 apperances.
By signing for Sydney FC, Yorke opted to continue his career in Australia for less money than might have been available in some other leagues, notably those in the Middle East (a common destination for ageing stars seeking a lucrative final contract before retirement). Qatar's football league were most interested, but Yorke opted for the Australian club instead. He scored the first goal for Sydney FC in its first A-League regular season match, a diving header against the Melbourne Victory. Dwight Yorke came to Sydney FC with the biggest pedigree of all players in the new A-League, having won the treble with Manchester United. He signed for two years. Yorke scored 7 goals in the A-League, with three of them being from penalty kicks. Former Sydney FC coach Pierre Littbarski moved Yorke into a midfield role and went on to give him the team captaincy.
He played a major role in leading Sydney FC to victory in the inaugural A-League Grand Final on March 5 against regional rivals Central Coast Mariners. He set up the only goal, scored by Steve Corica, in front of a sell out crowd of over 41,000 at Aussie Stadium, and was awarded the Joe Marston Medal as best player in the grand final.
Yorke was the marquee player for Sydney FC - meaning that his salary fell outside the salary cap. He was also a star name for the A-League as a whole. Aside from his footballing talents, the drawing power and credibility he brought both locally and internationally proved to be beneficial for the competition in its inaugural season, leading the FFA to use his image and name for the promotion of the A-League's second season.
In June 2006, Yorke trained with Manchester United in a bid to achieve a higher level of fitness prior to the 2006 World Cup, although he was at that time contracted to Sydney FC. This was because the Australian season had already ended and pre-season training had not yet commenced.
The transfer for a fee of £200,000 (AU$ $500,000) re-united Yorke with ex-teammates Roy Keane, now manager of Sunderland and Andy Cole, signed in August 2007. Yorke made his debut in the home match against Leicester City and received a rapturous standing ovation from home fans when he came on as a substitute in the first half. He scored his first goal for Sunderland in the 2–1 loss against Stoke and has become accepted by the people of Sunderland, switching on the city's Christmas lights in 2006. He has recently been handed the number 19 shirt at Sunderland, the number which he wore at Manchester United and Sydney. On the 2nd January 2008, during his teams 1-0 defeat to Blackburn, Dwight Yorke was given a red card by referee Rob Styles, who booked Collins, Wallace and Higginbotham in the same match. Dwight has been caught on record several times recently, stating he would like to return to the A-League, preferably Sydney FC. However following Sydney FC's recent signings, it seems very unlikely that Sydney would be able to fit him under the salary cap. It now seems that Dwight may end up playing for rivals Central Coast Mariners, the team bankrolled by the man who brought him to Sydney, Peter Turnbull.
On March 11, 2008 it was announced that The Mariners were in "Advanced Negotiations" with Dwight to become the marquee for two years. However on July 1, 2008 Yorke signed a new one-year contract to stay with Sunderland for the 2008–09 season . He demonstrated that he can still perform at the highest level with a man of the match performance against Arsenal on 4 October 2008, a game which Sunderland drew 1–1 away from home at the Emirates Stadium.
Yorke announced his retirement from international football in March 2007, choosing to focus on his club career at Sunderland AFC. He captained the side in Germany, and up until his retirement. However, he made a guest return appearance for a friendly against England in June 2008 after being invited by FIFA vice-president Jack Warner.
On July 10 2008, the TTFF announced Dwight's return to the national team for the 2010 FIFA World Cup qualification campaign .
The Dwight Yorke Stadium in Bacolet, Tobago, constructed for the 2001 U-17 World Cup, was named in Yorke's honour.
Dwight Yorke is also a cricket fan. One of Yorke's closest friends is fellow countryman Brian Lara, who is currently the all time leading run scorer in test match cricket. During the 1999 Cricket World Cup, Yorke made regular appearances bringing on drinks for the West Indies cricket team. Yorke's older brother, Clint Yorke, is a former first class cricketer who has represented Trinidad and Tobago as an opening batsman. 
He was said to have been dating former Miss Wales and Big Brother UK 2006 contestant Imogen Thomas. She reportedly finished her relationship with Yorke because "he was no longer famous enough". 
Yorke featured extensively in an episode of Australia's The Biggest Loser TV show, which aired 28 February 2006. The episode involved Yorke coaching the "red team" of contestants while they competed against the "blue team" in a game of football. Mark Rudan, Yorke's Sydney FC team-mate, was the manager of the "blue team".
For his contribution to the national team in the 2006 FIFA World Cup he was made a Sports Ambassador for Trinidad and Tobago.
Manchester United
Sydney FC
Sunderland