Henry Coleman saw WOAK as a stepping-stone in his career. An experienced producer and news director, he resented Holden Snyder's position as station manager simply because he was the owner's husband and deeply resented Holden hiring Molly Conlan (another inexperienced newsperson) as anchor. In Henry's eyes, WOAK's nepotism was interfering with his career. Seeing a common ally in intern Katie Peretti, Henry started to groom her for success. Not only did Henry encourage Katie's interest in Holden Snyder (possibly hoping that they'd have an affair, and Henry would get Holden's job in the fallout), but he went as far as poisoning Molly's sandwich so that Katie would have to take the anchor chair! When Katie had proven herself as capable, Henry went in for the kill and made sure that the photos of Molly's affair with Chris Hughes were displayed on WOAK's monitors. His plan was a success: Molly was forced to quit and Katie was promoted to head anchor. Henry continued to groom Katie for success by inventing a stalker to make her sympathetic and give her national media attention. Since Katie knew about all of his misdeeds, and told no one for fear of losing her cushy position, Henry knew he owned her and blackmailed her into silence. Unfortunately for Henry, his plans caught up with him and his schemes were all exposed by Molly. Fired from WOAK, Henry's career seemed ruined until Craig Montgomery, who admired Henry's ambitiousness, offered him a job at his newspaper, The Intruder.

Henry immediately clashed with Emily and Chris, who began digging into his past. Meanwhile, Henry suggested Katie fake a pregnancy to keep husband, Simon, going so far as to dress in drag as a mother-to-be when Katie and Simon visited the doctor's office. Needless to say, the plan failed. Meanwhile, Holden and Chris discovered Henry's connection to the horse Flashdance, which led to Henry's Hong Kong Syndicate connections, which led to threats on his life by both Craig and Syndicate operative Mei-Lin. Henry wisely hid away.

Henry eventually popped up again, agreeing to dig into Simon's past if Katie would convince Craig to write a letter of recommendation (Henry's ticket out of "Folkdale"). Henry unearthed the dirt, but Katie couldn't deliver the letter. When she needed his help shortly after, she forged a letter. Seeing through the ruse, he still gave her advice on her latest attempt to make Simon love her: Get rich. Katie's sudden lust for wealth led her to plan a destination to the island Lily and Simon were stranded on in the summer of 2000. More importantly, the island where the priceless Beloved diamond Simon came to Oakdale for had sunk to the bottom of the bay. Roped in by a promise to split the profits with him, Henry flew the plane to "Survivor Island", martini shaker and smart safari gear in tow. Unfortunately, Katie failed to realize the island had no runway, and the plane crashed. Even worse, the note Katie left for Simon was lost and remained lost for months.

Katie and Henry tried to adapt to life on the island, but someone stole their gear and food. That someone was the grizzly, longtime island inhabitant Cooley, who'd terrorized Lily the year before. Cooley took a shine to Katie, offering to give the items back in exchange for a night of passion with her. Katie agreed, secretly planning to lace her lips with knockout berries, kissing him as Henry conked him over the head with a coconut. When Henry begged off of violence, Katie forced him to dress as her (with a veiled hat covering his face), lacing his lips with the berries. Cooley quickly noticed his hairy legs (!), but it was his intense tickling which led to Henry's exposure as a sir, not a ma'am. Henry desperately clamped their mouths together, and Cooley passed out after some struggling. Henry and Katie buried Cooley up to his neck in sand. Clad in scuba gear, Katie miraculously located the diamond. Unfortunately, as she held her upraised hands to the sky, a bird swooped down and grabbed the ring in its beak!! Cooley (who had grown to respect Katie for her gusto) and Henry did their best to cheer up a despondent Katie. Henry even proposed marriage to coax her into a rage. But only rescue from Simon could make Katie happy, and that, as Henry repeatedly told her, was unlikely. Amazingly, Simon did find them. Since he only had a two-seater plane, and he hated Henry, Simon grabbed Katie and left. Henry was without his partner-in-crime and with Cooley. As a devastated Henry watched his last hope fly away into the sun, a bird flew into the wing of the plane. This was no ordinary bird, as Henry soon discovered. The bird crashed near Henry and Cooley. Clasped in its beak was a shiny object. Upon closer inspection, Henry grabbed the object, and, yes, it was the diamond!!! An overjoyed Henry could only laugh and call out to the vanishing plane, basking in the joy of one of Katie's harebrained schemes finally working in his favor.

Unfortunately for Henry, things didn't go as planned. After languishing on the island for months, he was finally picked up by a passing boat and made plans with Cooley to sell the diamond. Unfortunately, the pair needed the diamond's bill of sale to do it. Worried about the lengths Dooley might go to obtain the document, Henry tried to look for it himself. In over his head, and dealing with a violent partner, Henry was forced to confide in Rose D'Angelo and Paul Ryan. The search for the bill of sale led Henry and company to war-torn Avannya where Katie was almost killed. Seeing the diamond as cursed, Rose threw it in the ocean and Henry was forced to eke out a living back in Oakdale. To do this, he opened up a private investigator service with Katie and Simon. Soon, when Simon started behaving badly toward Katie, it was Henry who discovered the reason--he was trying to protect her from his former business partner, Bartleby, who was threatening Simon to help him with a con. Later, when Simon killed Bartleby in self-defense, he feared for his and Katie's life so he left Oakdale, leaving Henry a note to give to Katie only when necessary. A year later, Henry decided that the letter would give Katie a sense of closure and so he gave it to her. Unfortunately, it backfired with a determined Katie going off to Australia to find Simon. Months later, Henry was on hand to support Katie through Simon's presumed death, her hit and run with Mike Kasnoff, Katie's relationship with Mike, as well as Simon's brief "return from the dead." Henry found himself caught up in Katie's drama again when she became suspicious of Pilar Domingo, Mike's former girlfriend. Although Pilar claimed that she'd returned to Oakdale to escape an abusive lover, Katie had doubts and tried to convince Mike that Pilar was up to something.

A somewhat reluctant sidekick, Henry tried to help Katie prove whether or not Pilar was being honest. Unfortunately, their efforts only proved to paint Katie as mentally unstable and she was sent to a mental hospital. Wanting to protect Katie, Henry had himself committed as well and he and Katie remained committed for weeks. Fortunately for Katie, Henry was able to alert Simon to Katie's plight (by placing an ad in "Soldiers of Fortune" magazine) and Katie was rescued and Henry was released. Now safe, Simon informed Katie that he'd turned informant in Australia and he was safe from danger. He then, to Henry's dismay, asked Katie to go off and settle down with him in Australia. Sad to see his best friend leave, he was also concerned for her happiness since Simon had already hurt Katie by leaving her twice. Finally, the night Katie was set to leave, the whole episode ended with Pilar kidnapping Katie and falling on her on knife as Katie struggled to escape. Shocked at Simon's role in the Pilar debacle, Katie left town to clear her head.

After failing to win the affections of Nikki Munson, Henry suddenly ended up winning the heart of the woman he always loved--Katie. When Katie finally returned to town, she set her sights on Mike. However, by now, he was well-invested in his relationship with Jennifer Munson and decided to stay with her instead of reliving the drama with Katie. Not willing to just let Mike go, Katie settled on a plan to reel him back into her life--she announced her engagement to Henry! Although Henry was reluctant, Katie convinced him to go along with the plan, hoping that Mike would stop the engagement by declaring his love for Katie. To Katie's disappointment, Mike didn't take the bait. Meanwhile, in the course of their engagement, Henry seemed unusually quiet and serious; after a while, Katie figured out why--he was in love with her. When confronted, Henry finally admitted that he'd long had feelings for her but realized that she didn't reciprocate. He then told her that all he wanted was for her to be happy, and that was why he wanted her to be with Mike, since he knew that was what she wanted. Touched by Henry's declaration of love, Katie decided, despite her feelings, to marry Henry, whom she already considered her best friend. However, the Coleman marriage couldn't escape the specter of Mike, despite everyone's best efforts.

When Katie accidentally informed Craig that Jennifer was pregnant with his (and not Mike's) baby, Henry wondered if it was truly an accident--or was it an intentional ploy to break up Mike and Jennifer? Although Katie assured him that her feelings for Mike were over, Henry wasn't so sure, especially when Katie offered to plan Mike and Jen's wedding. Insecure as to where Katie's feelings really laid, Henry gave her a choice--attend the wedding or go to Hawaii with him. Though Katie agreed to go with him, when Henry was stopped for speeding, Katie impulsively bolted out of the car and made a mad dash for the wedding. Although she did nothing to stop the wedding, Mike had a feeling something was up and confronted her. As Henry secretly listened in, Katie tried to reassure Mike that all she wanted was his happiness. Neither man was fully convinced; Henry stepped out of hiding to tell Katie that their marriage was over. Although Katie was able to convince him to give them another try, it was obvious that her feelings for Mike weren't going away.

The final nail in the coffin of the Coleman marriage began with the arrival of Henry's teenaged sister, Maddie. Noticing the closeness between Katie and Mike, Maddie schemed to save her brother's marriage. When her attitude toward Mike caused her to be forced to leave, she arranged to fake an injury, only to have Henry accidentally get hurt. In the meantime, Maddie stepped up her plot to save her brother's marriage. To accomplish this, she did some investigating and found an old schoolmate of Katie's on the internet named Byron Glass and conversed with him, pretending to be Katie. She then sent Katie anonymous gifts to make Mike jealous. Unfortunately, Maddie's plan backfired when Mike and Katie accused Henry of faking his injury (which he was exaggerating) and of sending the gifts. To protect Maddie, Henry copped to it and he was thrown out. His marriage over, Henry had nowhere to live and lived out in his limo and arranged for Maddie to stay with the Hugheses.

Not long after, a mysterious person named BJ Green showed up in Oakdale, acting as Katie's benefactor. Although Katie couldn't figure out why this stranger was being so nice to her, Henry finally figured out that BJ Green was Katie's old classmate Byron Glass! Suspicious as to why BJ (who had lost a lot of weight since high school) would hide his identity from Katie, Henry confronted him. Although BJ tried to come up with an excuse, Henry was still unsure of his motives. BJ seemed more and more dangerous despite his best efforts. When Henry discovered that BJ was obsessed with Katie, he tried to go to the police but ended up being captured by Greene. In the end, Henry escaped captivity and BJ ran off after attempting to murder Katie and Mike. However, before he left, BJ withdrew a huge amount of money but was forced to leave the money behind in order to escape the authorities. To his astonishment, Henry found the money and kept it for himself rather than turn it in to the police.

Although he tried not to touch the money to avoid suspicion, he couldn't help himself and kept using the money. Finally Henry decided to bury the money in the woods. At the same time, Emily Stewart was in the woods trying to uncover the missing Paul Ryan's car. Seeing the abandoned car and Emily's agitated state, Henry ended up guessing that she'd killed Paul. Emily got Henry to keep her secret in exchange for her keeping his. She also agreed to hide the money for him in exchange for him helping her. However, Emily's mental state was far from secure and when she learned (with Henry's help) that Paul was alive, she became obsessed. Though Henry tried, continually, to get Emily to see reason and just forget about her former lover, she refused to listen. Paul finally returned to town at the same time Dusty Donovan disappeared and shocked everyone by confessing to his murder. Things finally came to a head when Emily told Henry she would give him all of his money back - as soon as he killed someone for her. However, Henry refused to have anything to do with murder. Meanwhile, Emily was becoming more and more unhinged, telling Henry that she needed to get rid of her rival, Meg Snyder. Again, Henry tried, but failed, to get Emily to see reason and she forced him to arrange a meeting with Meg. On the way to see Henry though, Meg was stopped by the police and evidence was found in her car implicating her in Dusty's murder. Suddenly, it occurred to Henry the only way that was possible was if Emily had been the one to do it! He confronted Emily who went psycho and threatened to kill him if he didn't give her the keys to Meg's room. In fear for his life, he consented.

Meanwhile, Emily had unexpectedly married Paul; at the same time evidence suggested that Dusty was alive. Unbeknownst to Emily, though, Paul suspected that she was holding Dusty captive and simply married her to find out where he was. He finally learned that Henry was working with Emily and tried to force an answer out of him, but Henry had no clue where Emily had Dusty. In the end, Dusty escaped and Emily was finally apprehended after fleeing and almost committing suicide. Although Hal wanted to arrest Henry for being an accessory to kidnapping, Emily stuck up for Henry and admitted that she acted alone. Weeks later, Emily finally told Henry where his money was. Unfortunately, the police had the money and Henry was forced to say that it wasn't his. In the meantime, Henry continued to be a friend to Emily and suggested that she might be able to avoid prison by pleading insanity.

A few months later, Margo approached Henry and warned him that Maddie was behaving oddly and acting out. Thinking she just meant normal teenage angst, Henry was shocked when Maddie was arrested for slashing up Lia McDermott's car in a jealous rage. Needing reinforcements, Henry called his sister, Eve, and asked her to come to Oakdale. When Eve arrived at the police station, Maddie confessed her darkest secret--while living with Eve and her husband, Louis, in Chicago the previous summer, she had snuck out to go to a frat party where she was raped. Eve decided to stay in Oakdale to help Maddie with her trauma. Unfortunately, Maddie was uncooperative--often sneaking out without telling Henry or Eve. On one such occasion, Lia was found murdered and Maddie had no alibi or no memory of where she was. Though Henry and Eve covered for her by lying to the police, Maddie still became prime suspect # 1. Soon after, another teenager was found dead and suspicion again fell on Maddie. A week later, Maddie was attacked by a masked person, though police suspected that she may have set up the attack to throw suspicion off herself. Other masked attacks followed and although Henry was steadfast in his faith, Eve voiced concerns that Maddie could be guilty.

Finally, Louis came to town and immediately clashed with Henry. Not only did Maddie seem terrified of him; Louis seemed overly concerned about her. Henry noticed Louis's obsession with Maddie and realized that there was no frat party--Louis had raped Maddie! After making it clear to Louis that he knew the truth, Henry confronted Maddie who finally admitted that Louis raped her while she was living with the Brownings in Chicago. Eve refused to believe it at first, but then realized it was true. Henry went on to theorize that Louis was the slasher and when they found the slasher's attire in his luggage, they realized they were right! With Maddie finally cleared of the murders and an APB out on Louis, Eve made arrangements for her and Maddie to move back to Chicago to live with their other sister. Maddie though, unexpectedly, told Eve she wanted to stay in Oakdale with Henry so Eve went back alone. However, instead of going to Henry's, Maddie made him believe she was going with Eve and then followed a group of teens, including, Casey, to Raven Lake. Suddenly, people started dying; by the time the police had reached the scene, four kids were dead. At the same time, Henry got a call from Eve and found out that Maddie was not in Chicago. Figuring out that she must have followed Casey to the lake, Henry went with Jack Snyder to find her. Soon after the duo arrived, Maddie unmasked the killer—Eve! Eve confessed that she was jealous that her husband was in love with Maddie and accused Maddie of playing the sweet little girl to get Louis to fall for her. She then admitted that she planned to frame Maddie for the murders and later kill her. As a demented Eve was being led away by the police, she chided Henry for his defense of "poor little Maddie." Henry told Maddie to not even try to make sense of it all since it didn't make sense.

Later, Henry met the wealthy and captivating Vienna Hyatt. The two instantly hit it off and soon became engaged. However, Vienna was fresh from a relationship with Brad Snyder, Jack's brother. Later, when Henry caught Brad and Vienna in seemingly compromising position, he canceled the wedding. Despite everyone's assurances that nothing happened, Henry's insecurities got the best of him and he decided it was best to cancel the wedding before he ultimately got hurt. Feeling badly, Brad tried to convince Henry to at least talk to Vienna but he wouldn't. Weeks later, the necklace that was stolen from Vienna was mysteriously returned; she was now free to leave Oakdale. Maddie urged Henry to patch things up with Vienna before it was too late. Though fear almost prevented Henry from telling Vienna how he felt, at the last minute he proclaimed his love and they reunited. Several weeks later, Henry won Al's Diner at a high stakes poker game. Though he was prepared to sell it, Vienna suggested they keep it but make it a healthier place to eat. Months later, things hit a temporary snag when Henry lost the diner in a poker game to a nefarious character named Gray Girard. Vienna was furious that Henry would gamble away the diner and Gray offered to give it back—in exchange for one night with Vienna. While Henry was appalled at the offer, Vienna didn't see a problem. To her, it would just be meaningless sex. At the same time, Gray tempted Vienna with expensive jewelry. Though Vienna returned the expensive bracelet to Gray, at Henry's insistence, it seemed that she missed that kind of life.

Meanwhile, Carly's son, Parker, was accused of murdering a man named Sam Hutchins. However, Carly and Jack were certain that a woman named Kit was the true culprit. Brad enlisted a reluctant Henry in their plan to get Kit to confess by having Henry pose as a realtor anxious to buy the property that Kit owned. Knowing that Kit hated Carly, Henry played on that by stating that he had an unpleasant past with Carly himself. When Henry stated that Carly could drive one to do anything, Kit agreed. In an effort to get Kit to implicate herself, Henry pretended to be attracted to her and began kissing her. At that moment, Vienna walked in and completely misunderstanding the situation, blasted Henry and ran out. Vienna ran right into Gray's arms and the two made love. Though Brad told Henry to tell Vienna why he was kissing Kit, Henry's pride got in the way and refused. At the same time, Vienna stayed with Gray who tempted her with talks of trips to Europe and expensive jewelry. Finally, Brad told Vienna the truth about what she saw. Horrified at her error, Vienna wanted to meet with Henry but he left her a note stating that he'd left town. At the same time, Henry was kidnapped and taken to a warehouse in Chicago. It didn't take Henry long to realize that Gray was behind this. After stewing for some time, Henry managed to get his cell phone and called Katie for help. Soon after, Katie and Brad rescued Henry. However, when Henry informed the police that Gray was responsible, someone else confessed to the crime.

Meanwhile, Henry decided that he wanted Vienna back and followed Brad's advice to beg. Though Henry begged Vienna for another chance, Vienna was uncertain. After all, Henry had made no move to marry her and already stated that he did not want children. Vienna began to wonder if a life jet-setting with Gray was preferable to a romance in limbo with Henry. Ultimately, Vienna chose love over money and she and Henry reunited at the church where they almost married. Not long after, Gray was revealed to be a dangerous man when he tried to kill the Hughes family. Luckily, Gray was shot dead by Lt. Margo Hughes in an effort to save her family. With Gray's death, all of his assets were seized by the government except for the diner—which was returned to Henry and Vienna. Months later, thanks to attorney Bonnie McKechnie, Henry and Vienna received a large settlement from Gray's estate for their pain and suffering.

Henry knew exactly what to do with the money—buy into Metro. His first obstacle was Carly, who didn't want a partner. An even bigger obstacle was Vienna who objected to the idea since she wanted to concentrate all of their energies on the diner. Vienna refused to budge since she was content with the diner. However, Henry was not content with just the diner—he wanted the glitz and glamour of the nightclub for himself as well as Vienna. When Henry attempted to trick Vienna into thinking that buying Metro was a good idea, she became upset and left town in a huff. Soon after, Carly finally relented let Henry buy into the nightclub. As Henry made himself at home at Metro, he befriended attorney Bonnie McKechnie, a known rival of Vienna's. Noticing that Bonnie's clients tended to be low life criminals, Henry suggested that Bonnie give up the law and go into a line of work that might make her happier—contesting at Metro. Bonnie quickly accepted his job offer. Not long after, Vienna returned and apologized for her resistance to owning the bar. However, she was extremely displeased to find Bonnie working there.

Eventually, Henry and Vienna heard that Brad and Katie wanted to start a family and Vienna told Henry that she wanted the same thing, but Henry wasn't wild about the idea. Henry was most insistent on not having kids. Vienna resorted to tactics as poking holes in Henry's condoms, but Henry caught her. Vienna even came close to choosing sperm donors, but changed her mind. Meanwhile, Katie was devastated to learn that she could not get pregnant. Wanting to help her friend, Vienna offered to be a surrogate. Vienna agreed to be injected with Brad's sperm and give them a child. Henry was totally against this, but Vienna wanted to experience pregnancy. Brad's sperm was extracted, but when it was being brought to Vienna, Henry purposely caused the doctor to drop it, but a second sample was taken and injected into Vienna.

A short time later, Vienna went to have an ultrasound to see how the baby was doing, but it revealed there was no baby, the insemination had failed. Vienna told Henry. Henry was secretly happy, but gave Vienna pity sex. Later on, Brad and Katie came to ask about the baby and Vienna said the baby was fine and Henry wondered why she was lying. In private, Henry asked Vienna why she was lying, but Vienna said she wasn't and proved it with a pregnancy test that came back positive. Henry realized that Vienna was pregnant again, only this time it was his baby! Vienna told Henry, that she was planning to give the baby to Brad and Katie when it was born. Vienna and Henry did everything they could to keep Brad and Katie from finding out the baby wasn't Brad's, even switching ultrasound printouts. Brad and Katie eventually invited Henry and Vienna to move in with them so nothing would go wrong. Henry started acting more possessive of Vienna's baby and soon realized that he wanted the baby and was willing to be a father. Vienna told Henry that she wanted to give the baby to Brad and Katie like she said she would, but Henry was against it. Meanwhile, Brad and Katie wanted to find out why Henry was acting so weird and they went to Memorial and found out that Vienna's insemination failed and realized that Vienna was pregnant with Henry's baby, not Brad's.

The news upset Katie and Brad so much that they kicked Henry and Vienna out of the house. Henry and Vienna went back to the Lakeview and Henry was determined to be a father to the baby and would not let anyone touch it. Vienna went to WOAK to try and talk things over with Katie, but Katie did not want to talk and in the argument, Vienna tripped over a cable and fell on her stomach. Katie so worried, rushed Vienna to the hospital. Sadly Vienna learned that she had lost the baby. When Henry learned of this, he was so devastated and blamed Brad and Katie for it. But they all soon agreed it was an accident. Vienna told Henry that they could try again. Henry thought it would be nice, but said that he needed time to get through this loss in one piece. Henry still wanted to have a child, but was not in a rush to try again and Vienna agreed to give Henry space.

Katie later learned that she had become pregnant by Brad. But Bob told Katie that Katie was going to have to take it very easy if she were to have any hope of having the baby. Katie was forced to give up her co-hosting job at WOAK and stay in bed. Vienna volunteered to fill in until Katie returned. Shortly after, a middle aged lady named Geneva Swift showed up on the show said what went on with Vienna and Brad was a sexual disgrace and it got high ratings and many phone calls. Vienna was not thrilled with Geneva Swift. Geneva kept getting offers from Kim Hughes to be a regular on the show, despite how much Geneva tried to turn Kim down, Kim did not give up. Geneva eventually gave in. Later, Brad told Vienna his suspicion that Geneva and Henry were having an affair. Vienna interrupted the live taping of Geneva at the Lake View and scolded Geneva for trying to steal Henry and grabbed her hair and literally pulled it off to reveal to everyone that Geneva was really Henry! Apparently, Henry masqueraded as Geneva because he was jealous of the time Vienna spent with Brad. Kim scolded Henry for pulling such a huge stunt like this, but let Henry off with a warning not to go near WOAK ever again. Henry tried to work things out with Vienna, but Vienna didn't want to talk and told Henry she was going back to Sweden to be with her mother for a while and left Henry alone in the hotel room.

Weeks later, Vienna returned and found that Henry had a visitor—his mother, Audrey. However, it was obvious that Henry did not welcome his mother's company. Though she was willing to forgive Henry, Vienna told Henry that she would only give him a second chance if he did the same for Audrey. Afterwards, Audrey dropped a bombshell—Henry was James Stenbeck's illegitimate son. Audrey discovered that Henry was the sole heir to Stenbeck's fortune. However, soon they learned that James was going to change his will so that Paul would be his sole heir. Audrey and Henry kidnapped James's lawyer before he could give James the revised will to sign. Audrey decided the only way Henry would inherit the money was if James died soon, so she stole a drug from the hospital and injected James with it. After the reading of James's will, much to Vienna's dismay, Henry decided he would give Audrey enough money to pay off the lawyer and Ray, the man she owed money to, but he would keep control of the rest of the fortune. When Vienna objected to Henry taking James' dirty money, Henry went to a mobster named Ralph to have it laundered and lied to Vienna that he was giving the money to charity.

When Barbara threatened to investigate the supposed charity that Henry was donating the money to, he agreed to split the inheritance with Paul 50/50. Unfortunately, Ralph was demanding all of the money. In order to get the inheritance, Henry seduced Barbara. Later, Henry was forced to confess all to Katie when she confronted him after she'd overheard him flirting with Barbara. Since Barbara showed no signs of giving up the money, Audrey attempted to poison her. Luckily, Henry caught on and prevented Barbara from drinking the poison. Not long after, Henry was horrified to learn that Katie had visited Ralph in the hopes of getting him to back off Henry. Unfortunately, Katie, who was pregnant with Brad's baby, was imprisoned and Henry begged Barbara for the money to save Katie's life. Though Katie was ultimately rescued, it came at a tragic cost when Brad was shot and killed while trying to save her. Afterwards, Henry gave Audrey the inheritance check, and ordered her out of his life. Barbara snagged the money as Audrey fled from Margo. Though Ralph tried to escape as well, Henry ambushed him. Meanwhile, Henry's friendship with Katie was in tatters since she refused to forgive him for Brad's death. However, given time, and the help of Brad's ghost, Katie forgave Henry and let him back into her life.

Meanwhile, Paul again declared that he wanted nothing from his father and gave the remainder of his fortune to Henry. Henry and Barbara fell into bed again and soon began relishing in their commitment free affair. However, it didn't take long for the pair to develop genuine feelings for each other. Unfortunately, Henry was torn between his feelings for Barbara and Vienna, who had returned to Oakdale. Vienna stunned Henry by proposing to him, and they made love. When Henry told Barbara about it, she dumped him. Afterwards, Henry bought Vienna a ring and accepted her proposal. Though he was seemingly committed to Vienna, Henry kissed Barbara when he learned that she was cancer-free. After learning that Vienna was pregnant, Henry decided to go through with the wedding despite his feelings for Barbara. Immediately after Henry married Vienna, Vienna broke the news that she lost their baby. However, Katie revealed to Henry that Vienna was lying—she had never been pregnant. Henry immediately annulled his marriage to Vienna and searched for Barbara who'd gone missing.

Barbara's captor turned out to be Gwen's mother, Iris, who demanded bank codes from Barbara, and forced her to write a short note to ask her family to give her time alone. Upon seeing the note, Henry became convinced that Barbara had been kidnapped. Barbara discovered a walkie-talkie and somehow tuned the frequency to Jacob's baby monitor. As she hoped, Henry heard the message when he was babysitting Katie's baby. Iris then relocated Barbara to the wine cellar at Fairwinds. Emily stumbled upon Barbara in the wine cellar. Iris tied Emily up and insinuated to Will and Gwen that Emily was behind Barbara's disappearance. Later, Henry caught Iris strutting around in Barbara's clothes and deduced that Iris had kidnapped Barbara and Emily. The family smelled smoke at Fairwinds and rescued Emily and Barbara from the cellar. Gwen detained Iris at the Lakeview bar, and the police arrested Iris. Barbara suddenly wanted nothing to do with Henry, who'd chosen Vienna over her, but after a poignant talk with Katie, Barbara accepted Henry's marriage proposal. Henry and Barbara received the cold shoulder when they announced their engagement to her sons, who were opposed to her marrying James Stenbeck's son. Henry withdrew his proposal, but Barbara insisted that genes wouldn't hold them back. When Paul learned that his mother had planned an impromptu wedding, he surprised the couple by gathering the family to witness the union. Later, Barbara decided to dissolve BRO so that she could concentrate on her new life with Henry who had bought Metro from Dusty.