Nemeses: Holden Snyder, Emily Stewart, Molly McKinnon, Carly Tenney, Mike Kasnoff.

After Katie’s and Henry’s schemes came to light at the 2000 Endicott Awards and they were both fired from WOAK, Henry moved to Los Angeles to try and pitch a movie based on recent Oakdale happenings. Having failed in that endeavor, Henry returned to Oakdale and has been hired by Craig Montgomery as the new Managing Editor of The National Intruder, much to Emily, Chris and Katie’s chagrin.

Henry’s involvement in the horse caper related to Flashdance was being slowly uncovered. Only discovered by Craig, Henry was heavily involved with Mei-Lin. Upon the revelation that Henry had been scheming against Craig the entire time, Craig summarily fired Henry from The National Intruder.

During Craig and Barbara’s wedding, Katie and Henry ducked out of town on a mission to recover Simon’s lost Rose of Sharon diamond. Due to Katie’s lack of foresight, the plane that was rented for the trip had no pontoons. Since Katie refused to give up on finding the diamond, she forced a crash landing of the plane.

After being stranded on Cooley's island with Katie for several weeks, Katie found (and lost) Simon's diamond just prior to Simon's arrival on the island to rescue her. Simon took Katie back in the pontoon plane and abandoned Henry to fend for himself with Cooley. As Simon and Katie were taking off, they hit the bird that flew off with the diamond, which landed at Henry's feet.

Nearly a year later, Henry finally escaped the island and returned to Oakdale. Back in town, he looked for the letter from Caroline Carpenter to Rose that would serve as the provenance to the Rose of Sharon diamond. Rose’s father was coerced out of town by Cooley’s son, lest harm come to Rose. Henry warned her about Joe’s precarious position, convinced her the only way to get Joe back unharmed was to bail Henry out, and hand over the diamond’s provenance. Rose did bail Henry out and accompanied him to Avanya, in an attempt to recover Joe. After successfully returning from Avanya, Lucinda tried to put Henry on her payroll. He first avoided this fate by helping Simon, Paul and Bonnie bug Marshall’s room in effort to tie him to Stenbeck. Henry ultimately joined forces with Katie and Simon, forming the PI agency Early Bird Surveillance. Henry also went to work for Rosanna to help her destroy Carly and Molly and broke into Molly’s place to find her burn unit check, and followed Carly to uncover who she slept with the night before her wedding to Jack. Eventually, Henry got a positive ID from the security guard at MC that it was Mike that Carly slept with the night before her wedding. Instead of going to Rosanna, Henry went directly to Carly and blackmailed her for $50,000 not to tell Rosanna or Jack.

Note: Licensed pilot.