On May 14, 2005, Trinidad competed against Winky Wright, in a fight where the winner would become the World Boxing Council's number one challenger in the Middleweight division. Wright won the fight by decision, receiving scores of 120–107 and 119–108 twice by the judges. Trinidad's fighting style appeared to be out of rhythm in the first round, while Wright presented a defensive stance and relied on jabs. During the first three rounds Wright was in the offensive scoring with jabs. On the fourth round Trinidad connected a solid combination. In the sixth, Wright continued the strategy used in the previous rounds while Trinidad employed a strategy where he tried to neutralize his opponent's punches by standing in front of him. In the later rounds Trinidad tried to take the contest's offensive but his adversary managed to block most of his punches while continuing his previous tactic. In the twelfth round Trinidad pursued Wright while trying to score a knockout, but his opponent boxed away from him until the round ended. Following this fight, Trinidad retired temporarily, after his father informed him that he would not continue in his corner.
On May 14, 2005, Trinidad competed against Winky Wright, in a fight where the winner would become the World Boxing Council's number one challenger in the Middleweight division. Wright won the fight by decision, receiving scores of 120–107 and 119–108 twice by the judges. Trinidad's fighting style appeared to be out of rhythm in the first round, while Wright presented a defensive stance and relied on jabs. During the first three rounds Wright was in the offensive scoring with jabs. On the fourth round Trinidad connected a solid combination. In the sixth, Wright continued the strategy used in the previous rounds while Trinidad employed a strategy where he tried to neutralize his opponent's punches by standing in front of him. In the later rounds Trinidad tried to take the contest's offensive but his adversary managed to block most of his punches while continuing his previous tactic. In the twelfth round Trinidad pursued Wright while trying to score a knockout, but his opponent boxed away from him until the round ended. Following this fight, Trinidad retired temporarily, after his father informed him that he would not continue in his corner.