Reggie first showed up at the free clinic after being stabbed in the stomach from a gang fight. When former Chief of Police Anna Devane dropped by at the same moment on another matter, Reggie, fearing Anna was going to arrest him, felt threatened and held a pair of scissors to pregnant Anna's neck. Remaining calm, Anna negotiated with Reggie, who finally gave up and was arrested. Charges weren't pressed. David's brother Trey Sheppard was a lawyer and took an interest in Reggie's case. Reggie had been moved around to a lot of foster homes and Trey came from a similar background. Trey took Reggie in as his foster son and got Reggie a job at Fusion Cosmetics.
Reggie was initially resistant to being helped by Trey, but Trey got through to Reggie and helped him out with turning his grades around at school. When Reggie found out Trey had a long list of illegal activity under his belt, Reggie accused Trey of being a hypocrite and not paying for his crimes. Once District Attorney Jackson Montgomery came knocking, Reggie gave Jackson proof that Trey burned down Erica Kane's house, which gave Jackson the opportunity to put Trey away for a long time. Trey gave himself up, on the condition that Jackson take Reggie in as his foster son. Jackson moved into Trey's loft and took over as guardian of Reggie.
With the Kane arsonist behind bars, Reggie earned the $50,000 reward Erica had offered. Jackson, quickly becoming a father figure, put the money into a trust fund (Reggie can't touch the money until he's in his twenties), despite Reggie's pleas to leave and take it to help his sisters (Jackson has revealed to Reggie that his sisters are in foster care, and Reggie retains contact with them).
After Jackson was shot, Erica insisted Jackson and Reggie move in with her. It was at that point that Erica and Reggie developed an unlikely friendship. At Fusion, Reggie found himself clashing with moral snob Joni Stafford, who felt she was better that Reggie.
Reggie was being threatened by street thug Luis, the guy who stabbed him. Luis once again came around, this time threatening Reggie's friend Joni Stafford. Luis told Reggie to steal supplies from the Habitat for Humanity site where Joni and Reggie were volunteering. Reggie refused, infuriating Luis who then held a knife to Reggie until he finally complied. Joni saw this exchange and helped Reggie cover up about the missing supplies.
With Joni's growing faith in Reggie, Reggie finally had the strength to stand up to Luis. Reggie stole Jack's gun and confronted Luis at the site. Just when Luis was taunting Reggie to pull the trigger, Jack showed up and talked Reggie down. Anna arrived and Luis was arrested for stealing the supplies. Later, Jack and Reggie reached an agreement with Anna where Reggie would be let off for holding Luis at gunpoint if Reggie agreed to give information on all of Luis's crimes.
Jackson legally adopted Reggie, giving Reggie a whole new family. After Michael Cambias escaped punishment for raping his cousin Bianca, Reggie was prepared to do whatever it took to protect Bianca from further harm. In a series of events that would be revealed months later, Reggie followed Bianca to Michael's condo one evening and realized she had shot and killed him. Reggie then helped Bianca's sister Kendall cover up the murder and dispose of the body. Bianca realized she had blocked out the memory of killing Michael and was cleared of all charges.
Reggie encountered teenaged runaway Danielle one day and housed her at Greenlee's apartment (Greenlee was out of town for a few weeks). There was an immediate attraction between the two, but Reggie remained unaware that Danielle was the daughter of Derek Frye (Pine Valley's Chief of Police), who Reggie has a rocky history with from his brushes with the law.
Reggie was devastated when Bianca's baby, Miranda, was presumed dead after a helicopter crash. In actuality, Paul Cramer had staged the crash and in a complicated scheme, Miranda ended up in the arms of an unsuspecting Babe and JR Chandler as their infant daughter Bess.
Danielle supported Reggie through the ordeal, a developing closeness that was threatened when Reggie learned the truth of Danielle's parentage! Derek discovered Danielle had returned to town and wasn't thrilled that she had taken up with Reggie Montgomery. As Danielle and Reggie began to get serious with each other, Derek grudgingly consented to their dating.
Reggie is extremely protective of Jackson's daughter, Lily, who is autistic. Lily has been mainstreamed into public high school, and Reggie and Danielle have both found themselves protecting her from the vicious manipulations of a popular clique.
