Father: Jackson Montgomery (adoptive)
Siblings: George Porter (biological; deceased), Numerous unnamed sisters, Greenlee Lavery (adoptive), Lily Montgomery (adoptive), Numerous unnamed sisters
Uncle: Travis Montgomery (adoptive; deceased)
Aunt: Barbara Montgomery (adoptive), Christine "Kit" Montgomery (adoptive)
Cousins: Bianca Montgomery (adoptive), Molly Montgomery (adoptive), Matthew Montgomery (adoptive)

Brother-in-law: Ryan Lavery
Significant Romantic Relationships: Danielle Frye

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. Later, Reggie was once again at the clinic after attorney Trey Kenyon saved him from being beaten up. It was then revealed that Reggie didn't have a home or anyone to turn to for protection and Trey insisted on taking Reggie in, despite Reggie's stubborn resistance. Trey was granted temporary custody, leaving Reggie's friend, Dr. Janelle Anderson, wary. Things seemed to be working out, as Reggie went to school and Trey arranged for him to work at Fusion. However, Reggie was still being threatened by street thug Luis, the guy who stabbed him. Luis threatened Janelle's life if Reggie ever turned Luis in for robbing Trey's apartment. In an effort to protect Janelle, a cornered Reggie turned Trey in during questioning as the person who burned down Erica Kane's house. Trey was arrested, and Jackson took Reggie on as a foster child. 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. 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' 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 has supported Reggie through this ordeal, a developing closeness that will be threatened when Reggie learns the truth of Danielle's parentage. Derek was none-too-pleased that his daughter had developed an interest in Reggie. Eventually, the two reached a tentative truce and Derek allowed the two to date. Reggie and Danielle have developed deep feelings for each other, and have nearly made love.

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.