Craig Montgomery and Sierra Estaban Montgomery are fictional characters and a supercouple from the American daytime drama As the World Turns. Craig has been played by Scott Bryce (1982-1990, 1993-1994, 2007-2008), Hunt Block (2000-2005), Jeffrey Meek (2006-2007) and Jon Lindstrom (December 3, 2008-present). Sierra has been played by Finn Carter (1985-1988, 1990-1991, 1994) and Mary Beth Evans (2000-2005, 2010).
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Craig Montgomery met Sierra Estaban when Craig's boss and Sierra's mother Lucinda Walsh ordered him to rescue her daughter from terrorists in Montega when Jacob Estaban's, Sierra's father, government was overthrown. Craig met a young man named Carlos burying Jacob and when they were attacked, the pair escaped. Later when Carlos removed his hat, Craig was shocked to she that he was really a she; and she was Sierra. Before they escaped back to Oakdale, one of Jacob's former generals gave Sierra a clue to reveal the identity of the mother she never knew - an emerald earring. Though Craig was previously infatuated with Betsy Stewart, he realized he was falling in love with Sierra and vowed to help her find her mother. Certain that Lucinda knew something about Sierra's mother, since she was unusually soft toward the girl, Craig did some investigating and discovered a faded picture. Confronted, Lucinda told Craig and Sierra that Sierra's mother was her friend, Mary Ellen Walters, who had died some years prior of a sudden illness. Doing some more digging, Craig discovered that Lucinda herself was Mary Ellen. Craig confronted his boss and agreed to keep her secret. However, later, Craig decided that he wanted to marry Sierra and felt that he couldn't do that unless he was honest with her. However, by the time Craig decided to be honest with Sierra, she had already learned the truth about Lucinda. Hurt that he kept it from her, Sierra ran off with another man, Tonio Reyes. Although he tried to find comfort with Iva Snyder, Craig just couldn't keep his mind off Sierra. At the same time, Sierra wasn't happy in her new marriage however and when Craig informed her that Tonio was having an affair, she had an affair with Craig. Sierra then became pregnant and finally decided to divorce Tonio. When Sierra's son was born, she and Craig (who had had surgery to correct his sterility) were elated to learn that Bryant was Craig's son and they married in her hospital room.
Then tragedy struck, when flying to Greece to help Betsy find Steve, Craig's plane went down and he was taken hostage by a Greek criminal. After almost a year, Craig was rescued by his family and returned to Oakdale only to learn that Sierra had disappeared in Montega and was presumed dead. Heartbroken, Craig tried to go on with life and began a relationship with Iva's younger sister, his employee, Ellie Snyder. However, when he got a lead that Sierra was alive in Montega, he left town in the hopes of finding her. He was successful and after the resistance was squashed, Craig and Sierra were able to reconcile and they moved to Miami so that Sierra could be close to Montega but their family would be safe from any terrorist attacks.
Craig briefly returned in 1990 and helped to clear Ellie who was being held under suspicion of murdering Brock Lombard; because he had proof of Ellie's whereabouts at the time of Brock's murder.
In 1991, Sierra would give birth to another child, Lucinda "Lucy" Montgomery.
Years later, Craig briefly returned to Oakdale after some marital problems with Sierra, and got involved with Lucinda's newly discovered sister, Samantha, and Emily again. However, in the end he realized he loved his wife and returned to his family.
Years later, we learned Sierra and Craig's marriage crumbled due to lack of communication and conflicting goals. Though the two tried to patch together their marriage, in the end Craig left Sierra and the two divorced with Craig leaving to roam the world. Sierra would send a troublesome teenaged Bryant to Lucinda's in the hopes that the boy would find direction in his life. Not long after, a wayward Craig made it back to Oakdale and though Craig and Sierra still had strong feelings for each other, they recognized that they were incompatible and remained friends. Following Bryant's death, a reluctant Sierra let Lucy stay with her father but visited often to provide guidance to her daughter and, at times, Craig.
A few years later, in 2004, Sierra would visit Oakdale again with a surprise—a new husband, Alan Drake. But as this new and exciting life was opening up for Sierra, Craig's life was falling apart since he'd lost his wife and newborn baby because he had adopted the baby illegally. Having lost everything, including Lucy's respect, Craig was on a downward spiral that included his drinking and embarrassing Lucy on her graduation from high school. Concerned about Lucy, Sierra suggested that she come to Montega for the summer. She and Alan then left. However, on the day Lucy was set to leave, she was suddenly kidnapped! Needing to know what was going on, but unable to leave Montega, Sierra sent Alan to Oakdale on her behalf. Weeks later, Lucy was found. Although it was originally thought that Dusty Donovan had kidnapped Lucy, in reality he was protecting her from the real kidnappers, who Dusty believed were hired by a member of Lucy's family. Although Craig would reluctantly voice his theory that Alan arranged the kidnapping to get ransom money, Sierra refused to believe it. Later, when Lucy was kidnapped again, Alan would end up getting shot trying to pay the ransom money. At the hospital, he whispered Craig's name before dying. With that, things suddenly clicked in Sierra's mind and she realized that Craig set up Lucy's kidnapping. After meeting with Dusty, and learning that he shared her theory, that Craig arranged the kidnapping so he could play the hero, Sierra decided to clear Alan's name and nail Craig. Although they did succeed in getting evidence against Craig, Dusty gave the evidence to Lucy, who refused to turn in her father.
Deciding that she had to protect Lucy from Craig's interference, Sierra moved back to Oakdale. She then decided to get revenge on Craig and force him to face the consequences of his actions by having him kidnapped. Planning to keep Craig locked up in a monastery until he repented, Sierra kept a close eye on him, via surveillance camera. The plan appeared to be working, with Craig praying for guidance and seeming truly sorry for what he'd done. Although she wasn't sure if he was being sincere or not, it became a moot point when he was rescued by his sister, Margo. Shortly after, Sierra left Oakdale though Craig remains in town.
Sierra returns to Oakdale briefly in 2010 on route to Washington D.C. She comes to visit Craig and, her mother. She offers Craig some life advice on changing his way for good, for the final time. This then causes Craig to re-evaluate the decisions he is making in his life. She then returns to Montega. Though Craig and Sierra have been labeled a supercouple, in the finale, Craig reunites with Rosanna Cabot, while Sierra continues to reside in Montega but offers Gabriel a job there.