In 1997, Kyle's mother, Diane Jenkins returned to Genoa City a well-respected architect. Victor Newman romanced Diane, and Diane and Victor were married. Diane decided she wanted a baby, so Victor countered that notion by having a vasectomy behind her back, but he had made a deposit at a sperm bank prior to the procedure. Diane was furious when she found out about the vasectomy. Then Victor's ex-wife Nikki was shot and Victor arranged with Diane for a quickie divorce so that he was free to remarry Nikki on her deathbed, so Nikki could die happy. The plan was for Diane and Victor to remarry after Nikki's death. But Nikki lived, and Nikki and Victor stayed married.

Diane intercepted Victor's notice from Robertson Labs saying the renewal time was due on his sperm deposit. Diane decided to steal the sample to become pregnant with the baby he had deprived her. Diane, posing as "Mrs. Victor Newman," showed up at the lab and arranged to have the deposit delivered to her penthouse where she kept it in a freezer in the closet of a locked room. But the deposit was stolen.

About a month later, Diane intercepted another letter stating, to her shock, that the sperm sample had been returned to the lab. She quickly went to a doctor, and she was artificially inseminated using the sample from the lab. After the baby's birth, she told Victor that the boy was his, and he insisted on DNA tests. Diane was shocked to learn the test showed her baby, Christian Victor Newman, was not Victor's child after all. Diane left town with her baby.

It was later disclosed that Nikki, with the help of Jack, had employed a detective's operative to get into Robertson Labs and switch the sperm samples to thwart Diane. But Nikki's attempt to help Victor resulted in Jack being the father when the man grabbed Jack's deposit as the nearest sample to replace Victor's. Diane returned to Genoa City with her baby, renamed Kyle Jenkins after Diane's father, with his nurse, Graziella. Jack then found out that his stored sperm had fathered Kyle.

Diane and Kyle moved into the Abbott pool house so that Jack could share custody. Then the Abbott pool house burned down and the police called it arson. Jack and Phyllis used the knowledge that Diane had done it as blackmail to get Diane to turn over custody of Kyle. But due to the friction between Jack and Phyllis, Jack eventually gave Kyle back to Diane. Diane moved to Chicago, taking Kyle with her.

In February 2010, Jack's new wife, Emily, asked Diane to return to Genoa City with Jack's son, Kyle, for a visit. After a short confrontation with Phyllis, Diane and Kyle returned to Toronto, Canada, where they lived.

In October 2010, just as Jack and Phyllis were celebrating their reuniting, the Abbott manor doorbell rang, and there stood Diane. Diane claimed to want Jack to get to know his son. Diane enrolled Kyle in school and gave life in Genoa City another try. While they lived in Toronto, Kyle had become quite the hockey-player, and he spent a lot of his time playing.

When Phyllis heard that her enemy Diane was staying in town and accepting a job with McCall Unlimited, Phyllis posted a story on the Restless Style website exposing all the dirt on Diane. Once Tucker saw the story, especially that Diane was not a partner in the company she worked for in Toronto, he rescinded his job offer. Later Diane attacked Phyllis for the article and Jack for apparently condoning it, and Diane told Jack he would never see his son again. While Diane was out of town, desperately looking for work, Kyle read the article, ditched his baby-sitter and confronted Jack and Phyllis, demanding to know if his mother had really done all the things in the article. Jack ended up breaking it off with Phyllis while he mended his relationship with his son and Diane. When Jack found a past-due notice for Diane’s room at the Athletic Club, he paid it for her until the end of the year, and also Kyle's tuition to Walnut Grove Academy.

Diane accepted a job at Newman and Victor's invitation for her and Kyle to move into the carriage house. Diane and Victor became lovers again, then she and Kyle moved into the ranch house with him. Victor began showering Kyle with hockey equipment, game tickets, and other gifts, and Kyle played hockey on the pond at the ranch. When Jack returned to town and discovered that Diane was now living with Victor, he insisted that Kyle live with him. After Diane got her son's blessing, Diane and Victor flew to Las Vegas, and were married. Phyllis and Jack later reluctantly dropped off Kyle to live at the ranch. But Victor fell back in love with Nikki again and told Diane he was getting an annulment. Being jobless again with nowhere to live, Diane got Jack to take Kyle to live with him.

Looking for revenge, Diane made a deal with Adam Newman to frame Victor for Diane's murder. She convinced Victor to sign papers to become Kyle's legal guardian as part of the setup. Adam gave Diane cash and forged identity papers in the names of Jennifer and Timothy Bilton. Diane sent Kyle to boarding school in Switzerland as Timothy, telling him not to contact anyone, and that she would be joining him soon. Jack confronted Diane about secreting their son away. Diane offered to hook up with Jack again to give Kyle a family, but Jack refused, so Diane told him that he would never see his son again.

Diane's body was found dead, floating face down in the stream in the park. Her diary disclosed that she was hated by so many that there were several suspects. Unable to contact his mother, Kyle phoned Jack from Switzerland but hung up, so Victor, Michael, Paul, and the police cooperated together to help locate him. He was finally identified by tracking children who traveled alone, and Jack went to Switzerland, told Kyle of his mother's death, and brought him home. Jack was livid when immediately upon their arrival, Victor handed him the papers giving him legal guardianship. Jack tore up the papers and vowed to fight it.

It took a full year to solve the case that a drunken Nikki had killed Diane in self-defense, then had blacked out, not remembering. Victor never laid claim to Kyle, and he stayed on living with Jack. After Christmas, Kyle begged Jack to attend high school at Northwood in Lake Placid, NY, accepting a once-in-a-lifetime offer to join their hockey program.

When Kyle Abbott returned to Genoa City in his early twenties, Kyle hooked up with Michael Baldwin's half-sister, Eden. Kyle became resentful when he discovered that his father Jack was romantically involved with Nikki Newman, the woman who had killed Kyle's mother. Kyle moved into the Newman Ranch and Victor gave him a job. Nikki then called off her affair with Jack for Kyle's sake. But after Abby had a heart to heart with Kyle, he apologized for being a jerk, telling Jack that he wanted him to be happy, and if Nikki made him happy, Kyle would have to get over it. So Jack declared his love to Nikki, and asked her to marry him again. Jack and Nikki were married a few months later, with Kyle refusing to attend the ceremony.

When Abby was arrested for pulling another publicity stunt where she led everyone to believe that she had been kidnapped, both they Abbots and Newmans washed their hands of her. Abby got off by paying a $100,000 fine, and only Kyle was there to pick up her when she was released. Kyle cheered her up by showing her the front page headline "Naked Heiress Kidnapping Hoax".

After Nikki left Jack the day after their wedding to hunt for the missing Victor, Kyle began helping Jack to walk again, and when Sharon turned into "queen of the manor" after Victor's disappearance and became CEO of Newman, Kyle quit his job at Newman, and moved out of the ranch and back into Abbott Manor with his father. A couple of months later it was mentioned that Kyle was working an internship in New York City on Wall Street. Kyle returned home after spending Thanksgiving with Traci and Ashley, and went back to work at Newman working for Jack who had become CEO.

Concerned that he would lose the only parent he had left, Kyle leaked to the press that Jack had become addicted to pain killers. But when that did not stop Jack from over-medicating, Kyle got Phyllis, Billy, and former alcoholic Neil to help stage an intervention. But Jack claimed they had insulted him, fired them all, and threw them out of his house. As Jack fought to get off the drugs, he realized that he had forgotten Kyle's birthday, and gave him a compass which he treasured that his father John had given him, passing on the hope that Kyle would always "know his true north."

Once Jack was himself again, he realized that he belonged at Jabot, not Newman, and left Newman in Adam's hands. When putting together his team to run Jabot, Jack hired Billy and Kyle, and Neil was made head of the new fashion division with Cane and Lily under him. A few months later, Abby returned to Genoa City and convinced Jack that she had finally grown up and to work for him at Jabot.

Abby warned Kyle that Summer Newman had crush on him, but he wouldn't believe it. Meanwhile Summer wrangled a job as an intern at Jabot working with Jack to be close to Kyle, and pumped Jack for information on Kyle. Unable to get Kyle to pay attention to her, Summer arranged for him to walk in on her without her blouse, claiming that she had spilled coffee on it. Kyle was mortified and tried to turn away, finally giving her his jacket to cover herself – just as Phyllis walked in on them. Phyllis saw through Summer's ruse and sent Kyle away. Phyllis told Summer that she wanted her first time to be special, that Kyle had no feelings for Summer, and she would only get hurt. Phyllis asked Summer, "How many times have you said you did not want to be like me?" and told her to back off.

Kyle walked out of his shower to find Summer naked in his bed. He asked her to get dressed, and told her he thought of her as family, as the little girl with her dolls. When Summer was not dissuaded, Kyle told her he was involved with someone else, and that she was too young. So Summer's friend Courtney gave her a makeover to show him she was no longer a kid. Kyle did a double-take when he saw Summer, but still told her no. But when Phyllis agreed to move in with Jack, Summer talked her mother into letting her move in with them too, so that she could live under the same roof as Kyle.

After Nick overheard Summer confiding in Avery about wanting Kyle to be her first sexual experience, he went ballistic on Kyle. As Summer told her mother how Nick over-reacts to the very idea of her and Kyle, Nick pulled Summer's paternity results from a locked box, showing viewers that it had been marked "cannot be verified" due to a damaged sample. Nick explained over Cassie's grave that he had lied about the results because he feared losing another daughter. But after Kyle and Summer appeared to be getting closer, Nick arranged a paternity test.

Summer accepted a prom date from Fen, but ditched the prom, dragging Fen to a party she had set up at her mother's penthouse instead. Everyone was drinking, and they played truth or dare. As a tipsy Fen completed his dare to kiss Summer, Kyle burst in to rescue Summer after receiving a text. Phyllis, who had just moved out of Jack's, arrived at the penthouse to find Kyle punching Fen in the mouth. She sent the other kids home and called Nick, Michael, and Lauren. Afterward, Nick arranged a paternity test.

Kyle asked Summer to dinner, and they kissed good night when he took her home afterward. Following Summer's high school graduation, she and Kyle went to dinner at the athletic club, and Summer suggested they get a room. Kyle talked her out of it, saying they were rushing things. Phyllis left to attend a focus group on eyeliner in Chicago, taking Kyle with her to keep them apart. Phyllis came on to Kyle, and after one kiss, Kyle called things off with Summer. The next day, Summer said goodbye to Faith, texted Kyle, and ran away to Chicago. When Kyle realized how much he had hurt Summer, he called her and apologized, asking her to return, and they would be together again.

Back in Genoa City, Kyle arranged to get Billy's club after hours, invited Summer, and gave her an armload of yellow roses, begging her to start over. Summer had to be the one to tearfully tell Kyle that she had found out that Jack was her real father which meant that they were brother and sister. Kyle walked out upset, unable to deal with it.

Jack and Jill were putting their heads together to come up with a way to get Chancellor-Newman away from Victor. Pulling in Devon, Kyle, Cane, Neil, and Jack's new assistant Hilary, they decided they needed a mole to work from the inside. Kyle volunteered for the job, but Jack turned him down, saying that unlike Victor, he would not use his kids to fight his battles for him. But while Hilary and Jack were going through a list of Chancellor-Newman employees for a possible candidate, Kyle was asking Victor for a job, telling him that he was tired of being Jack Abbott's son, wanted to be his own man, and to make a name for himself. Victor hired him but told him he had to cut his long hair, gave him full security access, then Victor had someone watch his every move. Victor began pitting Kyle against his grandson Noah, asking the two of them to present their ideas in front of each other, and choosing Kyle's over Noah's. But Abby talked them into working together instead.

Jill told Jack about a cancer drug research company that Chancellor had acquired while she was working there called Bonaventure Industries, and her suspicions that they were cutting corners trying to stop their losses. Jill pointed out that if they could prove it was an unethical subsidiary, it would create bad publicity with the FDA for Newman-Chancellor. Kyle offered to get more information on it, but Noah caught Kyle in Victor's office after Kyle had just photographed the file. Victor arrived and caught them fighting, then assigned both of them to the Bonaventure company to find out more about it. Noah returned and told Victor that he had caught Kyle in his office and suspected he was spying on Victor. Kyle disappeared from town with no explanation, but was referred to often as being in touch with Abby and Jack. At Christmas 2014, Kyle was said to be in Italy skiing with friends.

Kyle reappeared in Genoa City on Valentines Day 2015 when he was found trapped in a ravine near the Abbott cabin. He claimed that he had been on the way to Abby's party at the cabin, but later recalled peeping in the cabin windows and seeing the party-goers passed out inside. Kevin, Mariah, and Noah discovered a bloody towel hanging out of the trunk of Kyle's car, but Kyle said that he had had a bloody nose. Later that night, police broke the news to Summer that they had found Austin dead behind the wheel of a wrecked car, and Summer identified the body in the morgue.

Victor welcomed Kyle home, saying that he had heard great things about his work in New York City, and that Kyle's past spying on Victor had been forgiven.

Noah, Abby, Kyle, Mariah and Kevin comforted Summer as she watched Austin's videos on his laptop. One was of Austin telling Summer that rather than roses and candy Valentines, he needed to give her an apology. Saying that he did not like himself much lately, there was something she needed to know. But he never finished, as Summer had interrupted him. Abby left, and Kyle followed her to Crimson Lights. He told her that he had been in town a while and had been following them around, that he had confronted Austin about their affair, and they had fought. Abby begged him not to tell Summer.

During Austin's memorial service, Summer suddenly remembered an argument she had witnessed while drugged that night at the cabin. Austin and Abby were admitting they were having an affair. After Summer thanked everyone for giving Austin a second chance, she glared at Abby and shouted, "YOU slept with my husband!" All eyes turned to Abby, who was mortified and ran out.

Summer and her friends returned to the cabin following Austin's memorial service, and the armoire was opened to reveal "I know what happened here" written in lipstick on the mirror inside. Kyle told how he had returned to town, and after seeing them together, confronted Austin. They fought, and Kyle threw Austin a towel to wipe up his blood. After Austin's death, the bloody towel was found in Kyle's trunk by Kevin, Mariah, and Noah, and the DNA matched Austin's. Later after Kyle discovered that Sharon Newman had a motive to kill Austin, he wrote "I know the truth and so do you." in lipstick on her living room mirror, hoping she would crack.

Kyle tried to comfort Summer, telling her that she was the reason he had returned to town, that he wanted to be her protector to keep her from getting hurt again. Kyle kissed Summer, telling her that he needed her in his life.

After viewing some of Austin's videos that Kevin unencrypted from his laptop, they became convinced that they were being watched by someone who had murdered Austin because of some secret in his documentary they did not want exposed. When Courtney did not show up at her wedding to Noah, the young people all received a mysterious text asking them to meet her at the Abbott cabin. The group found Courtney dead in her wedding gown in the armoire. A note in her hand said, "I warned you. Stop digging." The police showed up, and the group had to admit that Austin had been murdered to explain Courtney's. Paul interviewed each and was appalled that none had come forward about Austin's murder, but understood that they had been threatened. No one in the group was arrested, but were told to keep their mouths shut, so the murderer would assume the police still thought Austin's death had been an accident. Kyle tipped Paul to Sharon's interview with Austin where she had told a Newman family secret.

Kyle escorted Summer to the benefit honoring her aunt Avery at the GCAC, then took her home where they made love for the first time. Noah walked in on them, looking for Summer to commiserate over Courtney. He left, upset with their behavior.

Kyle arranged a private dinner date, renting the GCAC rooftop deck with dinner prepared by a TV chef, hired a well-known singer/piano player, and gave Summer a diamond necklace. But Summer reacted by accusing Kyle of having changed, and not liking it. Summer explained that they had both come from money, but they had never been about the money, and walked out.

Fen suddenly returned from college and gathered his friends who were involved in the murder at the cabin. He admitted that prior to Austin's murder, he had been about to flunk a class, hacked into the college computers, and gave himself a passing grade so he could still get into law school. Fen had received an anonymous text blackmailing him into picking up a package containing the drug to spike the punch. Paul traced the DNA from the package to a wanted criminal named Marco Annicelli who used to head a South American drug cartel. The FBI got involved, and suddenly the DNA did not match.

Abby, Summer and Kyle visited Tobias Gray in the hospital after he had crashed his car, asking why he was following them and what he knew about the murders. Tobias said, "You need to know...Austin..." and died. Meanwhile, Kevin and Mariah snuck into Tobias' place where they found a 3D printer, fingerprint molds, and the stolen GCPD hard drives. But it all looked like setup.

Jack asked Kyle to drawn funds in his name to buy a shipping company. Jack called a meeting with Chelsea, Gabe, Billy, Kyle, with a hospitalized Ashley to be filled in later, convincing them it was time to overthrow the king and take the company for themselves. He explained how the money that he had Kyle draw to buy a shipping company actually was transferred into a dummy account in Victor's name, and how they were going to be diverting funds to the account to take Victor down for grand larceny and corporate fraud. But after Victor was arrested, Ashley had second thoughts, dropped the charges and claimed there had been a computer glitch.

Meanwhile, Kyle and Summer became lovers. But Summer feared that their battling families would end up tearing them apart when they had to choose sides.

Kyle is working in New York City temporarily, and rarely seen other than at family gatherings. He and Summer continued their long-distance romance.

Kyle returned to Genoa City (2016) because of Abby's miscarriage and apologized to Abby for being such a bad boyfriend, hoping she would give him another chance. But Summer let him know that she had moved on with Luca. Kyle warned Summer about Luca, reminding her what he had done to Marisa, then returned to New York City.

Two years later, Kyle cast the deciding vote to oust Jack as CEO of Jabot. Jack managed to stay by pointing out the by-laws provision that only a blood Abbott could be CEO, and that Ashley was not John Abbott’s biological daughter. Kyle returned to Genoa City just in time to find Victor in a coma after being assaulted, and Jack in jail as the number one suspect. According to emails, Kyle was guided by Victor in voting against Jack. Kyle visited Victor and made comments to the comatose Victor that they were in cahoots. Kyle bonded with his grandmother Dina, who had Alzheimer's. Kyle visited Jack in jail, and was obviously resentful for years of perceived mistreatment. Kyle moved into Jack’s office and took over as acting CEO, firing Jack’s key allies and longtime employees, including his loyal assistant, Gloria. Kyle planned to take Jabot public so Victor could buy the majority shares. Lauren was all for the IPO as it would enable her to buy back Fenmore’s. Kyle called a board meeting, and Phyllis was the deciding vote to approve after pressure by Lauren. Just released from jail, Jack arrived, declared the vote null and void, withdrawing the motion, and took over again. Kyle then had the nerve to ask to move into Abbott Manor with his family, but Jack relented. Kyle’s first assignment was to take Gloria’s place and convince everyone he had fired to return. Gloria returned with a hefty raise and a new title. Kyle was convinced that Ashley and Abby had a secret, and fished a memory chip out of the fireplace hoping to find it but the file was corrupted. He got Ravi Shapur to retrieve the data and gave the clip to Victor. Victor told Kyle to keep working at Jabot and report everything to him, even though Kyle was going to be carefully watched by both Jack and Billy. Sometime later, Kyle got Dina to confirm the video on the memory chip, that Jack was not John’s son, and knew he had to get the “blood Abbott” clause removed or he could never legally run the company.

Abby hired Charlie Ashby to edit the video, omitting that clip. When finished, Abby and Ashley prescreened and approved it. A theater was rented, the Abbotts arrived in a limo in formal dress. Victor showed up uninvited, but Dina let him stay. Everyone was enjoying the video titled, “What the mind can’t remember, the heart never forgets.” Ashley and Abby were shocked when the clip suddenly appeared. Jack was devastated. Victor gave condolences then laughed when Jack turned to leave. Later a DNA test comparing Billy’s to Jack’s DNA proved it was true. Jack moved out, and had to turn Jabot over to Billy. Accused by Kyle of rigging the movie to hurt Jack, Victor denied it.

Billy started a campaign for their newest product, a sunscreen called Birthday Suit, with swimsuit clad young people walking into businesses and handing out the product, which included Kyle. Billy was interviewed on GCBuzz Live at the GCAC Rooftop pool, and deciding it needed a kick, Kyle jumped in the pool and emerged with no swimsuit. The video went viral, and the show got in trouble with the FCC. But the product became a big hit making Kyle a hero.

Jack forgave Dina, but focused his life on finding his real father. Kyle agreed to help him every step of the way. Jack found a key among Dina’s belongings which opened a safe deposit box. The only thing inside was a group photo from the 1950s that included Dina with Philip Chancellor. Dina confirmed for Jack that this was the man who was his father. With Philip III and his son Chance unavailable, on a trek through the Himalayans, Jack petitioned to have the body of Philip exhumed to do a DNA test. It was fought by the Chancellor family, and Jack’s lawsuit was dropped when Dina proved to be an unreliable witness. But Kyle took matters into his own hands, dug up the body, and managed to grab a piece of bone before he was arrested. Both Esther and Jill showed up at Abbott Manor to give Jack and Kyle a tongue-lashing. Kyle poured on the charm with Esther, and Jack managed to calm Jill, reminding her how desperate she had once been to find her own biological father - until the DNA results arrived by messenger. They showed that Jack was not Philip’s son.

Kyle began helping Ashley oust Billy as CEO of Jabot. Ashley realized she needed to document every plan and irresponsible decision that Billy made, hoping to get enough information to present to the board and seek a no-confidence motion. After discovering $30,000 worth of work on Jaboat that never happened, Kyle wanted to lure Billy into gambling again, but Ashley nixed the idea. But Kyle went ahead with it, met Billy’s rival Sinead and convinced her to beat Billy so badly that he would need to dip into company funds. Billy was caught and ousted as CEO, with Traci stepping in as the only remaining blood Abbott. Traci took no time in abolishing the blood Abbott clause, and Ashley was elected CEO.

Summer had made a bet with Kyle that she could get Billy into bed. If she won, she would get Kyle’s classic car, and he won, he would get sex with Summer. Summer’s conniving failed and she found herself trapped on Jaboat for a weeklong cruise with no cell or wifi. When it came time to pay off on the bet, Kyle tried to seduce Summer with a stripper dance. But when he realized that Summer was emotionless about it, he faked that he fell asleep. The next day he admitted he was still in love with her. Summer felt bad, said she loved him too, but like a brother. She still wanted to stay friends, but Kyle said didn’t know him at all.

Jack called a board meeting after Kyle discovered that Andrew Lynford had been blackmailing Ashley, and she had been paying him off as Type A Consulting with company funds. Ashley introduced him as Dr. Andrew Lynford a consultant doing anti-aging anti-cancer research. But Phyllis recognized him as a former coworker from twenty-five years ago at DNS Labs in New York City, and knew he was now in charge of the DNA lab at Genoa City Memorial. Jack offered Andrew double for the real reason Ashley was paying him. Ashley gave the answer for free, telling them all that Jack was really John Abbott’s son, how she had coached Dina, edited the clip in movie of Dina’s memoirs, and had paid Lynford to alter the DNA test results. Ashley had gotten her revenge for what Jack had done to her by invoking the blood Abbott clause. She said she had intended to tell Jack the truth as a Christmas present. Ashley was removed as CEO.

After a bad conversation with Ashley, Dina told Kyle that she had been a good mother to Ashley and there was proof of it at Jabot. Kyle took her to the CEO office that had also once been John’s. Dina located a wall safe that had been covered during remodeling, her birthdate being the combination. Inside was a document that John had drawn up assigning all patents, inventions, discoveries made by Ashley to her excluding all others in perpetuity. Knowing what this information could do to the company, Kyle tried to destroy it, but Dina pitched a fit, and Jack walked in. Once Jack saw the contract, he shredded it, ushering them out, saying it was best for the company. After Dina later related the tale to Traci, Traci found and reconstructed the shredded document. She called a family meeting and made Jack and Kyle tell Ashley what had happened that day. Ashley was both elated and furious with them. Jack tried to buy back the patents from Ashley, but she stood her ground requesting the CEO position in exchange. When that was rejected, Ashley decided to pack up her patents, move to Paris and start her own cosmetics company.

Jack, Billy and Phyllis all vied for CEO of Jabot, but Phyllis won the election due to the Abbotts splitting their votes, and by hiring Kerry Johnson as lead chemist, whom both Abbotts had been trying to lure. Hoping to be named her COO, Kyle jumped in, coming up with cost analysis and ideas for Phyllis. But Phyllis named Lauren COO, and asked Billy to resume his former job in marketing.

Lola Rosales arrived in Genoa City and set up her truck in the Jabot Cosmetics company parking lot. Jabot employees raved about her food, and others came from elsewhere after the news spread. Kyle ordered food one day but asked for variations. Lola resented his trying to augment her cooking. Intrigued by her spunk, Kyle flirted with her, but she accused him of being a spoiled rich kid who always got his way. He asked Lola for a date. She agreed only if he would try her food as it was. He did, and agreed that she was right.

Kyle and Lola began dating, but Lola was continually getting upset with how much Summer was still in his life. Summer finally took a job with Newman Enterprises in Dubai, making one last play for Kyle before she left. Kyle rejected Summer’s advances, telling her he was in love with Lola. For Christmas, Kyle gave Lola a $5,000 purse, and she gave him a discount store watch. When Lola found out how expensive it was, she broke it off, saying how Kyle just didn’t get her at all. Kyle tried to win her back, and convinced her to make her dreams come true by agreeing to Abby and Devon’s offer to be the head chef at their new restaurant venture. Lola made it clear that she was saving herself for marriage. Kyle said he could live with that, and they reunited. Lola, with Kyle’s support, cooked a 4-course meal as an audition and convinced Devon and Abby to hire her.

Kyle invited Lola to the Abbott cabin for Valentines day, but she turned it down. Summer, back from Dubai and inserting herself into his life daily again, showed up instead. Meanwhile Jack had a heart to heart with Lola and sent her to the cabin. Summer convinced Kyle to take her on the sleighride in Lola’s place, and they were kissing as Lola walked in. Summer wouldn’t stand down, making it look like Kyle was lying about their intentions. Lola ended things for good and left. Summer tried to tell Kyle they were meant to be, but he left. Kyle found Lola, tried to explain, but she refused to listen. Realizing she had forgotten her coat at the cabin, Lola borrowed Abby’s coat and left.

Rey’s wife Mia had a drunken argument with Abby over Arturo, who had to pull them apart. Later Mia thought she found Abby at Abbott Manor, but it was Lola in Abby’s hooded coat there to reunite with Kyle. Mia smashed Lola’s phone and knocked her down from behind, causing Lola to hit her head, and fall into the pool in freezing weather. Kyle found Lola, pulled her out, and called 911. Later in ICU, Lola’s brother Arturo knowing they had broken up, made Kyle leave. Lola’s brother Rey vowed to make the attacker pay. Mia was there clinging on Rey, shocked to find out that she had attacked Lola instead of Abby. Lola was in a coma. They also discovered that her liver was failing, and she needed a donor. Rey, Arturo, and Kyle were tested but not a match. After Kyle talked Mariah into doing a segment on GC Buzz with him requesting a donor for Lola, Arturo let Kyle see Lola. It was Kyle who brought Lola out of her coma. Summer got tested and told Kyle she was a match. Kyle said he would do anything to convince Summer to save Lola, even marry her. Summer refused, saying she was not the type of person who could be blackmailed into a loveless marriage. She then convinced Kyle that he still loved her, he went along with it, and she agreed to help Lola if he would marry for a year, and if not happy they would divorce. Summer then made Kyle propose publicly at the athletic club. Kyle agreed so long as he was the one to break it to Lola. They were married the day before surgery which both Lola and Summer came through fine. Kyle tearfully told Lola that the anonymous donor had been Summer, how marrying her was the only way he knew would convince Summer to donate. Kyle told Lola he loved her and had been willing to make the sacrifice to save her. Lola said she thought Kyle still loved Summer, that she was grateful, and sent him to his bride. Both sobbed after they parted. The next day Lola thanked Summer but said she hoped to never see her again. Lola was taken home by Rey. Kyle and Summer told Jack, Phyllis and Nick about Summer saving Lola. Nick gave the newlyweds his land on the lake for the house he never had built for him and Phyllis. Meanwhile they were living at Abbott Manor, and Summer was great with Dina.

Ashley returned exposing that Kerry (whose name was really Dominique) had been working for her, and all Jabot patents since Ashley left had been licensed to her dummy company, Premiere Cosmetics. She had Jabot over a barrel with no product to sell, and left them a contract good for 24 hours making Jabot a wholly owned subsidiary of her company, and offered to keep them all on. Phyllis wanted to sue Ashley, but admitted that Kerry had no non-compete clause in her contract. Held responsible, Phyllis was voted out as CEO and off board. Jack gave his case to become CEO. Lauren felt that Ashley’s deal was only option. Abby abstained, Kyle sided with Jack, and Billy’s became the deciding vote making Jack CEO. Lauren offered to buy back Jabot’s 49% stake in Fenmores. Jack refused, needing Fenmores as the only arm of company making a profit, but promised they would talk if Lauren could come up with the money. Jack, Billy, and Kyle met the next day making plans for the survival of Jabot, including making Jabot a complete package, clothing, shoes, and cosmetics. Summer joined them and she and Kyle were full of ideas about bloggers, social media, and giving them a box of samples, let them go online, and report. Jack offered Summer a marketing job, working with Kyle which she eagerly accepted. They contacted Theo Vanderway, agent for social media influencer Nazanin, and Summer schmoozed them into working with Jabot.

No longer able to carry on the charade of marriage with Summer, Kyle asked her to divorce. Summer was devastated, but agreed, knowing that his heart and mind was always on Lola. Kyle impressed Lola by preparing an island atmosphere for dinner on the roof of Society, and later they made love for the first time in hotel room. Lola told Kyle how it had felt to be abandoned by her father before she'd been born, and being brought up by a mother with a broken heart. 

Summer reported to Jack that Kyle was not keeping up his end of their business partnership, skipping out on social engagements with clients to be with Lola. Seeing that Summer was carrying the load and yet successful, Jack reassigned Kyle.

The sweet relationship between Kyle and Lola blossomed until they decided to move in together. Lola refused to move to the opulence and ever-present family at Abbott Manor. Luckily this coincided with Rey moving in with Sharon, so Kyle and Lola took over his apartment above Crimson Lights. Kyle kept trying to please her by attempting to make the apartment their own, but failed at do-it-yourself projects, which they managed to complete together instead. Kyle shocked Lola by asking her to marry him. She thought it was too soon, but later changed her mind and accepted, and Kyle got the blessing of Rey.

Kyle promised Lola the wedding of her dreams and planned it all himself. Lola chose Abby to be her maid of honor, and Kyle chose Jack as best man. Rather than let Kyle’s old New York City pal Theo throw Kyle a wild bachelor party, Mariah arranged a co-ed Miami-themed party for the couple on the roof of the Athletic Club. Theo threatened to bring Zoe to Genoa City to darken Kyle’s past. It turned out that Kyle, on the rebound from Summer, had lived a wild rich boy lifestyle in New York City, including designer drugs, women, with unlimited funds. Kyle and Theo had thrown a party at their place at which Zoe had gotten so drunk she got alcohol poisoning. Discovering she was only 17-years-old from her ID, they had taken her to the ER and left her there. But Zoe’s father confronted Kyle, threatening to press charges of endangering a minor after his under-age daughter nearly died, and Kyle had paid him $100,000 not to.

Guests arrived at the romantically decorated venue, and Lola was in awe. Her wedding gown was beautiful and she and Kyle glowed. Lola’s mother Celeste showed up, and Lola invited her to walk her down aisle with Rey. Theo arrived with Zoe, who said she had no hard feelings, it was not their fault but hers, she was glad they took her to the ER, and too bad her father made it all about money.

Kyle and Lola honeymooned in Samoa, and returned to new living room furniture courtesy of Kyle. Lola countered with a couch-party watching the Brewers series games she had DVR'd for them.

Months later, Adrian showed up, in trouble, with a black eye claiming there was a husband looking for him. Kyle gave him money to go away. Lola found out and was upset, but Kyle told her it was a onetime thing. Adrian met Traci in the lobby of the Grand Phoenix Hotel and bought her drink. He was last seen schmoozing the clientele of the hotel.

Jack took a leave of absence and made Kyle interim CEO while he was gone. Later Jack added Billy as Co-CEO. They didn’t get along. And Kyle was not happy that Lola and Theo were becoming friends. Then while doing research for the Abbott Family Memoires, Jack and Traci discovered that Dina and Stuart Brooks had produced a baby just out of high school who turned out to be Theo’s father Eric Vanderway. After getting a DNA test confirmation, Jack welcomed his nephew Theo into the Abbott family. But Traci and Kyle were not thrilled at all that they were cousins. Kyle hinted at dark secrets in Theo’s past. Ashley was charmed by Theo and offered him a job working for her in Paris. But Jack talked him into working at Jabot in Genoa City instead. Kyle became Co-COO with Lauren Fenmore, Summer became head of marketing, and Theo head of Social Media. Later Kyle negotiated with Jack to become Co-CEO with him instead. Later Kyle negotiated with Jack to become Co-CEO with him instead. Theo proved successful, coming up with Jobot-jies, a Circe Brands partnering deal, and with a Korean Skin care line.

Theo and Summer broke up when she realized she was still unable to get over Kyle. And Kyle suddenly decided he had really loved Summer all along, and he told Lola they were over. Kyle and Summer became inseparable, at work and away. Lola began confiding her heartbreak in Theo. During a winter storm, Lola and Theo were stuck at Society with no power. They cuddled up together to keep warm and ended up in a passionate kiss. Meanwhile Summer and Kyle were returning home, the car slid on ice, and out of commission. They walked to Society and joined Lola and Theo riding out the storm.

Although Jack warned Kyle and Theo to let go of their animosity, for the good of Jabot, it never happened. Jack finally gave them a challenge, a week to come up with a plan to rebrand Jabot. After discovering that Theo had hired Jabot secretary Kendra to look for dirt on Kyle, Summer and Kyle plotted to set them up to find the Jabot Back to Basics presentation that Jack had made 15 years ago. When Theo presented it to Jack as his own, Jack fired him. Kyle’s presentation “Welcome to the Future of Jabot” won. Jack made Kyle Co-CEO with him.

Theo disclosed to Sally that Kyle had an affair 4 years earlier with Tara Locke, wife of Ashland Locke, a dangerous rich guy with a world-renowned reputation of vengeance. And that both men were still unaware that her 3-year-old son Harrison had been fathered by Kyle. Sally let Kyle know the information would stay between them so long as they peacefully coexisted. Kyle had to tell Summer before she found out otherwise. A paternity test proved it was true. It wasn’t long before Tara arrived in town wanting Kyle to protect her and Harrison from Ashland who had found out. She and Harrison moved into Abbott Manor. Ashland divorced Tara and was ready to kill Kyle until he found out that he had cancer and was dying. After falling in love with Victoria Newman, Ashland decided to let Kyle get to know Harrison. Jack also became very close with his grandson.

Summer and Kyle became secretly engaged using a knotted cherry stem for a ring. Nick found out and promised them the house he had been building for him and Chelsea as a wedding present. Kyle and Lola finally got divorced and Kyle and Summer made plans to elope. But Kyle woke up the night before the wedding, Summer was gone, and she only left a vague note. She returned a month or so later saying she couldn’t handle being a mother to Harrison. Summer suddenly got an offer to become creative director with Marchetti fashions in Milan, accepted it and left town. Kyle found out later that she had been coerced by Sally to take the job and leave town so Sally could get Summer’s job at Jabot and have a chance with Kyle. Kyle moved to Milan with Harrison to be with Summer. They had a small civil ceremony wedding in Milan attended by Newmans and Abbotts that fans never got to see. They made a brief appearance at Victoria and Ashland’s wedding in Tuscany just days later.

Seven months later Kyle was summoned by Jack to Genoa City to break the news that Jack's son Keemo had died leaving Jack a young adult granddaughter. And that Jack had found this out from Diane, Kyle's mother who had faked her death when Kyle was a young boy. Diane said she had spent the years since learning to become a better person, and she wanted to be a part of Kyle's life again. Jack explained all that he knew and left the decision to Kyle who asked to see her. Diane apologized and explained that everyone hated her and it was the only way for her to escape them. She could not take Kyle and be forever on the run. Kyle reminded her that he had grieved for her and that several people had been accused of her murder. Diane agreed to attend an Abbott family meeting where everyone told her what a horrible person she was. Diane agreed, but still claimed to be a new person. Diane explained faking her death was more about protecting him from living on the run with her or knowing she had abandoned him. Kyle was torn about Diane.

Mariah was thrilled that Kyle happened to be in town. She asked him to get an Internet ordainment and officiate at her wedding to Tessa. Kyle agreed and did a great job. Diane crashed the after party, watching from the wings.

While visiting in Genoa City, Summer admitted to Kyle that Marchetti fashion was in financial trouble, likely her marketing expertise was why they hired Summer. Summer proposed to Kyle that Jabot buy out Marchetti and get back into the fashion business, allowing Angelina to continue working from Milan but allowing Summer to return home to Genoa City. Jack researched it and agreed to the deal. Kyle and Summer moved back to Genoa City and Kyle became CEO of Marchetti.