1986: Mercenary Matt Connolly decided to put an end to his life of action and adventure and settle down in the quaint town of Pine Valley. Little did his know, appearances were deceiving. Erica Kane hired Matt to pilot a news helicopter to break out his old friend Jeremy Hunter, who was wrongly imprisoned for the murder of Earl Mitchell. Jeremy had called on Matt's services earlier that year to save Erica and Brooke English who has crash landed in South America.
Matt became Adam Chandler's lackey in his ploy to publically embarass Travis Montgomery, Erica's latest beau. Matt showed off his racing skills in Travis' annual car race, appealing to Robin McCall.
Matt dated Nina Cortlandt, but their relationship was doomed from the start. Nina was still very much in love with her first husband, Cliff Warner. The couple accidentally ran into Cliff while visiting Martha’s Vineyard. Matt knew his relationship was doomed. He could see Cliff was still in love with her too. After the breakup, Matt confronted Cliff and told him to stop hurting Nina and admit to his feelings. By the end of the year, Cliff and Nina remarried.

1987: After Cliff’s apparent death at the hands of rebel soldiers in South America, Matt worried for Nina’s mental health. Matt followed Nina to Martha’s Vineyard where she wanted to be alone with her thoughts. Nina begged Matt to leave her alone, but Matt refused. Her rage turned into passion, and they made love that night. Nina asked Matt to marry her. The next morning, they eloped.
Back in Pine Valley, Cliff made a surprise return. Nina cheated on Matt to be with Cliff again. But, when Cliff learned about Nina’s marriage to Matt, he left her. Matt tried to pick up the pieces of their broken marriage.

1988: Nina was pregnant with Matt’s son. Matt knew that their marriage would never work out if they remained in Pine Valley. Matt got a new job in the Mid-west, and the Connolly’s left to make a new home there.

1989: Nina insisted on returning to Pine Valley when their son, Mikey Connolly, fell ill with a strange disease. Matt knew she wanted Cliff’s opinion about the situation. Though Mikey would be cured of the ailment, another bombshell was waiting for the Connolly’s: Mikey was Cliff’s son. Matt knew that Mikey was the only thing stopping Nina from turning back to Cliff. He packed his bags and returned to Chicago without Nina.