Caleb was forced to move from his mountain home into his nearby cabin when Erica Kane's plane crashed into his house. Caleb rescued the pilot and Erica from the plane. Caleb rushed the pilot to a nearby hospital, but left Erica stranded on the mountain. Erica refused to be left behind, so she followed Caleb to his cabin. Caleb didn't know who Erica was and was clearly annoyed by her presence in life. Eventually Jackson Montgomery and Krystal Carey found Erica and took her back to Pine Valley.
After Erica was rescued, Caleb could not stop thinking about "Dorothy," which was his nickname for her. Caleb was summoned to the reading of Palmer's will and was bequeathed Cortlandt Electronics on the condition that he work with Erica and change his name to Cortlandt. Caleb also was forced to move into Wildwind, which Palmer had purchased prior to his death. When Erica tried to get Caleb to sign over his shares of Cortlandt, he refused. Greenlee and David Hayward tried to buy back the mansion from Caleb, but Erica informed Caleb that they were the ones who had sabotaged her plane, so he refused to sell to the Haywards. Caleb changed his surname from Cooney to Cortlandt in September 2010.
Erica and Caleb each claimed they had no interest in working together, and Caleb did not want Palmer's company or a life in Pine Valley, so he planned to sell Cortlandt Electronics. Erica went on a pre-wedding honeymoon with her fiancé, Jackson Montgomery, and she expected to return home and find Caleb had returned to his old life in Pigeon Hollow.
Instead, Caleb had decided to fight for his uncle's company with Erica by his side. J.R. Chandler tricked Caleb into selling the company to Chandler Enterprises. Caleb overheard Scott Chandler mention that they had stolen something from the Cortlandt family. Caleb revealed Adam Chandler had taken something from him before, and this time the Chandler family would not succeed. Scott Chandler eventually confessed and served prison time for stealing nanotechnology that belonged to the Cortlandts.
The attraction between Erica and Caleb grew, although Erica continued to profess her love for Jack. Erica began to confide in Caleb instead of Jack, and Erica discovered Caleb's son, Asher Pike, was in Pine Valley. Caleb had been in love years before with Asher's mother, Sonia, but she had engaged in an affair with Adam Chandler. Sonia went into labor while searching for Caleb in a coal mine. She was killed when the mine exploded. Caleb was too overcome with grief to raise his child, so he allowed Palmer to arrange Asher's adoption. Before his death, Palmer had arranged for both Caleb and Asher to arrive in Pine Valley.
Asher knew Caleb was his father, and he blamed Caleb for his mother's death. Asher worked for J.R. and moved into the Chandler mansion so he could help J.R. destroy Caleb. When Asher fell down a flight of stairs after an argument with Caleb, Erica arrived and informed Caleb that Asher was his son. While Asher recovered in the hospital, Caleb tried to form a bond with his son. Asher refused Caleb's attempts, and he publicly accused Caleb of murdering his mother.
As time passed, Caleb continued to forge a relationship with his son, much due to the encouragement of Erica. Caleb had a locket with a picture of Sonia delivered to Asher, and Caleb told Asher about the accident that had killed Sonia. Caleb also reached out to Erica and confessed his love for her. When Erica continued her plan to marry Jack in St. Barts, Caleb showed up and promised Erica he would be waiting for her when she was ready to admit her feelings for him.
Erica disappeared before the wedding, and she made a phone call to Jack, claiming she could not go through with the wedding. She had not taken off with Caleb, but had been kidnapped instead. Jack and Caleb worked together to successfully rescue Erica, but Asher was injured in the process. Asher had known his father cared deeply for Erica, so he had joined the search and had severely injured his legs in a quarry explosion. Caleb remained by Asher's side while Asher recovered.
Although father and son became closer following the quarry accident, Asher turned down Caleb's offer to move in with him and instead returned to the Chandler mansion. Caleb visited Asher there and he thanked J.R. for the kindness he had shown to his son and he warned J.R. that Chandler Enterprises was on shaky ground. J.R. accused Caleb of planning a takeover but he insisted he was only providing a friendly warning.
Caleb and Erica were still running Cortlandt Electronics but Erica showed less interest in the company after her rescue from the quarry and seemed more interested in media attention than working. Caleb offered Liza Colby a position working with him which she initially declined. A few weeks later after the mayor had fired her from her position as District Attorney she accepted Caleb's offer.
Asher also accepted an offer of Caleb's and moved in with him. Caleb overheard a doctor speaking to Asher about a painkiller addiction and he intervened to take care of his son. After Asher overcame his addiction, he and Caleb planned a fishing trip to Caleb's old cabin. They stopped at Krystal's before their trip where they ran into Liza and her daughter Colby. Caleb flirted with Liza and asked if she was interested in him. She replied that she was and agreed to go on a date with him.