After some years, Ray settles in Miami and is now working as a hit man. He is known as The Specialist as the explosives he plants do not harm innocent bystanders. His services are in great demand, yet he is extremely picky about the cases he takes. Most of the demands are made over the Internet, and one such person who contacts him is May Munro (Sharon Stone), he becomes her confidante and she discloses to him that her parents were killed by three men who work for Tomas Leon (Eric Roberts), incidentally, Trent heads security for Joe, his father. May persuades Ray to help her infiltrate Leon’s circle, he refuses and tries to talk her out of it - but she insists that she will go ahead irrespective of whether or not he helps her. May uses the alias Adrian Hastings.
The lower rung of the ladder in Leone’s organization is hit by police, which is when Trent uses his influence to get onto the bomb squad. Tomas on the other hand is attracted to May alias Adrian, who takes advantage of this new angle to their relationship to get closer to him. Ray kills two of the men May identified as her parents murderers - however, Ned gets suspicious and forces Adrian to side up with him, so that Ray’s cover is blown and he can also get even with his enemy from the past - he has sworn vengeance as the CIA asked Trent to quit.
Ray sets up a trap for Tomas, he is killed and since Adrian was with him at that time - everyone believes that she is dead, too. Joe Leon is livid, and spares Trent his life only so that he can sniff out his son’s murderer before the funeral. Ray and Ned are both under the impression that Adrian has also perished in the bomb blast - however, when he gets a message on the Internet and replies thinking its May - it turns out to be a hoax, for which Trent is responsible. A crestfallen Ray goes to attend May’s funeral, only to be pleasantly surprised that she is alive and well. Trent, also expecting this to be Adrian’s last rites, is in for a rude shock, when he sees that the body in the casket is someone else’s. Furious, Trent meets Adrian and she makes a feeble protest, lamely excusing herself - not one to be conned twice, Trent asks his sidekick to escort her out to his car - on the way out she goes to the restroom and calls Ray up to warn him.
The Captain wires the entire hotel room, and detonates it when Trent’s men enter. A persistent Ned is relieved that he can still have his revenge when the two are led into a much booby trapped building - however, he walks into one himself and is killed. The Specialist was the third highest grossing box office hit for Stallone in the ‘90s, and although audiences were disappointed with the lack of romance between two of the most desirable onscreen pairings - Stone and Stallone - yet, worldwide audiences also welcomed the new look sported by Ray aka Sly - clean and cool, not sporty or jungle maverick!