In August 2008, Clint Buchanan hatched a plan to get Buchanan Enterprises back from Dorian, who had seized control of the company several months earlier in a hostile takeover. Clint had discovered that Dorian's foster daughter, Langston Wilde, had a living blood relative and decided to use this information to force Dorian to give up control of the company. It turned out, however, that Langston's relative was in a Columbia prison serving time for murder. Clint arranged for the dirty warden of the Columbia prison to release Ray. Jared Banks, who was dating Clint's daughter Natalie and was on the outs with Clint, agreed to fly down to Columbia to retrieve Ray. Ray initially was not interested in the offer, but soon warmed to the idea when he was told he would be paid handsomely for his efforts.

Ray arrived in Llanview just as Langston had accepted Dorian's offer to adopt her. During a party to celebrate the impending adoption, a finely dressed and cleaned-up Ray showed up at La Boulaie and announced that he was Langston's uncle. He claimed he had lost touch with his sister and only recently had discovered that she had died. He had just found out where Langston lived and came to town because he wanted to meet her. Langston believed it all, but Dorian immediately knew that there was more to Ray than met the eye and she expedited efforts to adopt Langston. While at the courthouse to make her adoption of Langston official, Dorian was stunned when Ray entered the courtroom and demanded legal custody of his niece. The judge sided with Ray, since he was Langston's only living relative, and Ray promptly announced his intention to return to Columbia with Langston. Dorian became livid, overturning a table and threatening to get even with the judge. The judge then cited her for contempt of court and threw her into jail for the night.

Back at the Buchanan mansion, Ray and Clint were discussing the courtroom events when Cole Thornhart overheard the two men and confronted Clint. Later he told Langston and the others about Clint's role in bringing Ray to town. After apologizing to the court, Dorian was released and quickly learned from the teens that Clint was behind everything. She marched over to the Buchanan mansion, where she told a shocked Clint that she had no intention of giving over the company. Dorian then hatched her own plan to make Ray go away permanently by paying mobster Jackie McNaughton to put out a hit on Ray. Her family was livid that Dorian refused to give up the company in exchange for Langston's freedom, but Langston said she understood and admired Dorian for not backing down. A tearful Langston then prepared to leave behind the life and family she had come to love in Llanview.

After one failed attempt to kill Ray, the hit man hired by Dorian headed to the airport where Ray and Langston prepared to depart. Dorian had second thoughts about ordering a hit on Ray and told Jackie to call it off, but he said it was too late. She spied the hit man, who was dressed as an airplane pilot, moments before he was about to fire and shouted that he had a gun. John McBain, who had been tipped off by Addie Cramer that Dorian had hired an "exterminator," showed up in the nick of time and shot the gun out of the hit man's hand. As it happened, Ray's younger wife Vanessa and his teen-age daughter Lola had just arrived at the airport from Columbia. Vanessa picked up the gun and aimed at Ray. Ray was shocked to see Vanessa before him and reached out for his daughter. Vanessa took the gun and shot Ray in the chest.

Ray was rushed to the hospital, where he underwent surgery and survived. Meanwhile, Langston and the others learned that Ray had been in jail for murdering his first wife. Lola, Ray's daughter, had witnessed the shooting and testified against her father in court. But in the hospital, Ray told police detective Antonio Vega that he was innocent and had been set up by Vanessa. He warned Antonio that Vanessa was poison and that his brother, Cristian, was in danger as long as he associated with her. Ray then was escorted from the hospital, on his way back to Columbia and prison.

Téa Delgado returned to Llanview in December 2008, ostensibly to represent Todd Manning in a criminal case. But representing Todd was just a cover for who really brought Téa to town: Ray Montez. For the past year, she had been representing Ray Montez in his efforts to get released from jail. Ray maintained contact with Téa by phone, as she tried to get close to Vanessa by marrying her off to old friend Cristian Vega and earn Lola's trust. Téa even had Ray send Lola a letter in which he proclaimed his innocence and pointed the blame at Vanessa. Lola eventually admitted to Téa that she wasn't sure that her father had killed her mother. Lola said Vanessa led her to find the knife that had killed her mother hidden inside a jewelry box, and convinced her that her father must have planted it there.

Téa was getting closer to getting the proof she needed against Vanessa, but Ray got impatient and busted out of the Columbia prison again and made his way to Llanview. He broke into Cristian's loft, knocked Cristian out and cornered Vanessa upstairs. Armed with a knife, Ray threatened to do to her what she had done to his first wife. Cristian came to, however, and a fight ensued between Ray and Cristian. Téa, who had just been told of Ray's escape by authorities, showed up at the loft with Lola just in time. Cristian was shocked to learn Téa had been representing Ray this whole time, but was even more shocked when Vanessa admitted that she had married Ray for his money and had framed Ray for his wife's murder. But Vanessa said she hadn't killed Ray's wife. The authorities arrived and put both Ray and Vanessa in jail. Ray's conviction for murdering his first wife was overturned, and Vanessa was sent back to Columbia.

Ray decided to stay in Llanview to renew his relationship with his daughter, who was staying with Langston at La Boulaie. Chef Moe Stubbs, who had assumed ownership of the home from Dorian as part of a convoluted scheme by Dorian to win over David Vickers, invited Ray to stay at La Boulaie. Dorian, who had newly married David, returned to her home after David went to Hollywood to try out his acting career and was not happy to learn that a "convicted killer" was living under her roof. Ray, meanwhile, appreciated Dorian's spunk and her fierceness when it came to protecting her family. Their petty squabbling soon gave way to a passionate kiss, which Dorian resisted as a matter of pretence but really enjoyed. When Tea, eager to get Todd Manning out of her system, asked Ray out on a date, a jealous Dorian showed up and tried to turn Ray's attention to her. But Ray refused to play along, telling Dorian that she should decide whether she wanted to be with her husband or with him.

Ray was with Dorian at La Boulaie when Dorian got a call from David, who was excited about a new television commercial he had just filmed. Dorian invited Ray to watch the commercial, hoping to make him jealous by flouting her husband's successful career, but the commercial turned out to be for a hemorrhoid cream called Hav-A-Seat. Dorian was embarrassed, but then she and Ray shared a passionate kiss. Jack Manning snapped a picture of the encounter with Dorian's cell phone. Dorian later sent the photo to David, who returned to Llanview and broke things off with Dorian, freeing her to continue her relationship with Ray. While Langston and Lola were at the prom, Ray and Dorian enjoyed the house to themselves. Ray serenaded Dorian on his acoustic guitar and the two ended up in bed. Lola barged into the bedroom as they were making love and was obviously high on drugs. She admitted to poking holes in condoms Dorian had given Langston for her first time with Markko, and then stunned Ray and Dorian when she admitted to having killed her mother many years ago when she found out she was cheating on her father. Ray was devastated and stayed with her as Lola was taken to St. Anne's psychiatric hospital for evaluation. Dorian later planned a big feast for Ray, but when Ray arrived he told Dorian he was taking Lola out of state so she could recover. Dorian felt betrayed, and rejected Ray's attempt to give her a parting kiss.