In 1986, Pearl became involved with Courtney Capwell, a Capwell clan cousin. She helped him get hired as the Capwell chauffeur, after Dylan Hartley caused him to lose his job as a waiter. Pearl didn't get along with Courtney's bitchy sister, Madeline, and later found her murdered. He was arrested and charged with killing Madeline, but Courtney paid his bail. It was then revealed that Pearl was actually a Boston Brahmin named Michael Baldwin Bradford III. He and Courtney became lovers.

That same year, Pearl had himself committed to a sanitarium to rescue Kelly Capwell, Courtney's cousin, from the evil clutches of Dr. Rawlings. Pearl knew Rawlings, who he believed had caused his brother Brian to commit suicide years before. Eventually, Pearl helped Kelly escape from the sanitarium. He also fell in love with her. As a result, Pearl and Courtney broke up.

When Pearl learned that his brother Brian was alive, he launched a search for him. The brothers ultimately reunited. They also found out that Courtney was Madeline's real killer.

In 1987, Pearl helped reunite Cruz and Eden while the three of them were traveling on the Orient Express. He was heartbroken when Kelly didn't want to be more than friends. Later, he got a job (along with Elena Nikolas and Carmen Castillo) at the new detective agency Cruz opened up. During this time, Pearl had a sexual fling with Elena, who turned out to be a psychopath with plans to kill the Capwell children!

In 1988, Pearl stopped being a detective in favor of becoming a waiter again. He befriended Jake Morton and fell in love with Rita Grant. When Rita became ill and was hospitalized, Pearl and Jade took care of her baby, Carrie. Unable to tell Rita how he felt about her, Pearl started writing anonymous love letters to the young woman. She soon found out that he was her secret admirer and thought it was very romantic. When Jake left town, Pearl and Rita were among his friends to say goodbye to him. They weren't seen again, and Pearl was then said to have left town.