Winston Halcoyn
The Waging Winston






Retired Power Broker


Winston Halcoyn (legal name)


William Halcoyn (father; deceased)
Rosanna Halcoyn (mother; deceased)


Ralph Grendel (half-brother)
Marylin Kincaid (half-sister)


Mona Daniels (ex-wife)
Mary Ann Werner (ex-wife)
Mona Radish (ex-wife)
Tanya Rockford (ex-wife)
Mary Ann Werner (ex-wife)
Mona Halcoyn (wife)


Catherine Andrews (ex-girlfriend)
Mae Reyes (ex-lover)
Olivia Kramer (ex-girlfriend)
Mary Ann Werner (flirtation)


Derwood Halcoyn (son)
DeDe Halcoyn (daughter)
Conrad Halcoyn (son)
Blair Werner (daughter)


Haley Kramer Grendel (niece)
Sandra Grendel (sister-in-law)
Emma Irving Grendel (niece)
Ray Jordan (nephew)


Winston Halcoyn is a sim in the fictional town of Sun-Crest Point. One of the series original male characters, Winston has had to deal with the constant disapproval of his father, his mother's abandonment and, return. As well as, the roller coaster that is his personal life, while trying to run a major corporation, the discovery that he has two half-siblings and, raise two children. He has also served as an antagonist at certain times.


In the beginning, Winston is the son of town villain and businessman, William Halcoyn and Rosanna Halcoyn. He is married to Mona Halcoyn and together they have a son named Derwood. He is the CEO at Halcoyn Communications, his father's business. He, along wiht the rest of his family reside up at Halcoyn Hill, the welathy part of Sun-Crest Point. Winston is labeled Will's protege and is being groomed to take over the business. However, his father begins to poison Winston's mind into thinking that Mona is trying to sabotage him. Winston loves Mona and at first refuses to believe his father's claims that she would intentionally try to hurt him or his career. After a series of unfortunate events that appear as if Mona is trying to ruin Winston he does begin to believe his father's accusations. He and Mona engage in a series of fights and she tries to express her feelings for him but she eventually decides that she can't handle being a Halcoyn any longer, takes Derwood and moves out and begins to live with Daria Grendel. Later when Daria's plan to reunite Winston and Mona fails, William reveals to Winston that years ago he cheated on his mother with Daria and together they had a secret love child and Winston's half-brother, Ralph Grendel. Winston then goes to talk to Mona but catches her and Ralph kissing and leaves the scene immediately and infuriated. Later Ralph reveals that at the time he didn't Mona was his wife and that he didn't know he ven had a half-brother.

Winston believes his borther's claim and the two actually seem to get along. However, Winston refuses to forgive Mona and later goes to her house and tells her he wants a divorce. He then meets Catherine Andrews, in a cemetery one afternoon while he was visit his mother's grave. The two hit it off and Catherine proves to be a great distraction for Winston. She begins to make frequent stops by the office and Winston eventually asks her out and they begin dating. Winston then allows Mona to throw a birthday party for their son up at Halcoyn Hill. during the party Daria sneaks in along with a secret guest who is supposed to reunite Mona and Winston, who still love each other. It is revealed to be Winston's long thought dead mother, Rosanna. Rosanna then exposes William and his truly twisted and evil nature. After that Winston and Mona run to each other's arms and are happily reunited, thus ending his romance with Cathy. After that Mona and Derwood move back into Halcoyn Hill and Winston tells Will he is done with him and to keep to his wing of the manor. He then invites Rosanna to come move back into Halcoyn Hill, seeing as it is her home too, she accepts and apologizes for lying to her son for so long. He accepts her apology. William makes his opposition to Rosanna living there known, but his pleas fall on deaf ears. Mona and Winston then end their divorce proceedings, however, Winston doesn't know that Mona and Ralph did more than kiss during their separation, they slept together.

Eventually Winston's suspicions get the better of him and he hires PI, Cassidy Free, to investigate what happened between his half-brother and wife during their separation. Mona then reveals that she is pregnant and it is hinted that the baby might actually be Ralph's. Eventually Mona's guilt consumes her and she confesses that she and Ralph did sleep together. She then goes into labor and gives birth to a daughter, Deirdre "DeDe" Halcoyn. and it is revealed that Winston is indeed the father of DeDe. However, he is angry with Mona and refuses to forgive her for her betrayl and they get a divorce and Winston retains custody of Derwood and Mona gets custody of DeDe. Mona would later leave town with DeDe and Winston would enter into a state of coldness. His father notes that he was right about Mona and this seems to bridge the gap between the two. Winston then begins to develop a "relationship" with Mary Ann Werner, whos a little younger than Winston and un-known to him, her intial intentions toward wooing him was so she could mryy him, get a divorce and take that vast majority of his fortune. After Catherine took all of Mary Ann's father's money when he died. After a short romance Mary Ann and Winston marry and she moves into Halcoyn Hill, and becomes Derwood's step-mother. Their marriage is a cold and distant one from the start. However, William seems to approve of Winston's decision of Mary Ann. Winston then learns that he has a half-sister, named Marylin, that his father had as a result of an affair with his long-time assistant, Lila Kincaid.

Soon after his father and mother's second marriage ends his father begins to see Lila and becomes a real father to Marylin. Days later Mary Ann discovers a strange smell going through the compound and stumbles across a dead William. When his will is read it is revealed that he and Lila had eloped and that he left all his money to her and Marylin. He also decided that when Marylin is of age she will assume the spot as head Power Broker for Halcoyn Comm. and until thne Ralph is to assume the position. Thins deeply anger Rosanna and she tries to get Ralph to deny the offer and pass it to Winston. However, Winstont ells his mother not to worry and that he doesn't care. He then discovers his mother's relationship with his then brother-in-law, Arnold Werner, and is disgusted but tells in time he can come to grips with it. Days later his mother passes away as a result of erratic mood failur over what William had done to her her entire life. Winston then becomes almost comatose and Mary Ann consoles him and this leads to a confrontation after Rosanna's funeral that causes Winston to break down in Mary Ann's arms and confess that eh misses his parents and wishes he had a better relationship with them. This seems to save his marriage to Mary Ann, however, during this time Mary Ann was supposed to be pregnant, which was a lie she created because she felt Winston slipping away from her when he learned that Mona had re-married to a man named Colin Daniels. Soon after this Daria Grendel, arrives at Halcoyn Hill and informs Winston that at his mother's funeral Arnold confessed Mary Ann's inital intentions to her, and his as well.

Winston and Mary Ann then get into a bitter argument and she confesses that she is not pregnant but only said so because she felt him slipping away from her. Winston then tells her it's what she wanted wasn't it. Mary Ann then reveals that her plan had changed and that she has actually fallen in love with Winston and she wanted to ensure the security of their marriage. He tells to get out and they have a brief separation. Then Ralph makes a bad business deal with Lucia Reyes's second husband, Carter Irving, than practicallt bankrupts Halcoyn Comm. Until, Mary Ann and Arnold come to the rescue and offer to use their shares in their father's company to help stabelize and keep the Halcoyn business afloat and they succeed. This also seems to help Winston and Mary Ann reconcile their marriage. However, they hit unstable ground again when Winston learns that Mona will be returning to Sun-Crest Point, with a now toddler aged DeDe as her second husband has passed away. When she does return Mary Ann begins to notice Winston's happy behavior when he is around Mona and their children and begins to feel he still loves her and after a heart to heart with Mona, Mary Ann divorces Winston and tells him she is looking out for her best interest. This hits Winston hard as though he is free, Mona is not as she begin to date Arnold. He then confesses his woes to his assistant, Mae Reyes and she tells him about her and her husband's, Escobar Reyes, separation and the two bond and share a kiss in Winston's office.

This kiss eventually leads to more and Winston and Mae begin a physcical relationship. They share an emotional connection but when Escobar leaves Donna and professes his love for Mae she and Winston have a talk where he tells her to reconcile with Escobar and their affair is ended, on good terms. However, Mona and Arnold then become engaged and he decides that he should try nd move on in a real relationship and he begins to date Sandra's sister, Olivia Kramer. They seem happy and connect but Winston's love for Mona remains strong. Alas, neither of them are willing to confess their love because they feel the other is happy without them. Then as Mona begins her procession down the asile she tells Arnold that she doesn't love him and that she is in fact in love with Winston. This causes Olivia to break up with Winston realizing she can't come between true love. Mona then tells Arnold to go to the woman he is in love with, Karen Collins. Mona and Winston then reunite. Shrotyl after their reunion they decide to re-marry privately in their home with just Derwood and DeDe present. Winston and Mona then embark upon a long period of happiness. When Haley, Franky and Emma are kidnapped Winston, Mona and Derwood stumble across the children by accident. The kidnapper is revealed to be Carter Irving, Ethan's father who almost runined HE. This leads to Winston and Derwood fighting Carter and freeing the children. But before that all went down, Winston began to prepare for Lila Kincaid's return and his sister's Marylin Kincaid's take over of the company.

When Marylin does return, it is quickly esablished that she is mearly a puppet of Lila's. Winston, Mona, Arnold and Ethan are all fired. Derwood is almost fired but Amanda Campbell comes to his defense. Winston and Ralph attempt to reach out to their sister but Lila continues to manipulate Marylin's emotions and tells them how they never reached out to her before. They then try to trap her into a confronataion alone but she gets her way out and fires Bart. Then a talking to from Mona and Sandra prompt Marylin to turn against her mother and she sees her for who she truly is. Lila leaves the business but takes a great ammount of the comapny funds with her, bankrupting HE again. This is when Mona's second husband, Colin Daniels, who was thought to be dead returns. He remakrs that his marriage to Mona was dissolved by his supposed death but he desires to win her back. This is later revealed to be a ploy and that this "Colin" is a con man who tells Mona that if he really wanted to he could have her marriage to Winston invald and making them still married. He then tells her to give him 1,000,000 simoleons and he'll vanish, leaving her alone. She agrees and does this but the money is then revealed to have the stability cash for the company. This sends Winston into a frenzy as he tries to find new investor and investnet opportunities. This is when he meets young, wealthy widow, Tanya Rockford. However, as time goes on it is hinted that Tanya is using Winston and she is soon revealed to be in cahoots with George Snyder, who impregnates Tanya ordering her to reveal the child as Winston's. The boy, Conrad, soon becomes Winston's third child.

Yet, with the return of his second wife, Mary Ann, his marriage with Tanya suffers, and so does her plot. Winston also helps a now widowed Mary Ann regain custody of her sons after her deceased husband's parents took custody of them. In the ensuing process the two grow close once again and even share a kiss as Mary Ann Wins custody. However, Mary Ann refuses to admit that there are any lingering feelings, and demands Winston see his marriage to Tanya through. Yet her declaration becomes transparent as she helps expose Tanya as a gold digger and rather a pawn in George's revenge plot again Winston for his father, William's involvement in George's families deaths. Winston soon divorces Tanya, but she doesn't inform him that Conrad is actually George's son. Winston and Mary Ann continue to grow closer as he leans on her for support. Eventually they share another kiss, but Tanya tries to use Conrad as a means to win Winston back, but to no avail. Tanya then decides to leave town and reveals that Conrad is George's son. Hurt, but fearing that George could be using this as a way to get revenge on Winston he orders a paternity test which in fact reveals Winston as the boy's father, to George and Tanya's shock. Regardless, Tanya relinquishes custody to Winston and leaves town, while George is saddened to realize he never really had a son. With Tanya out of the way, Winston boldly declares he has fallen back in love with Mary Ann, who returns his feelings after trying to hold back. The two then become engaged again, and in the 200th storyline marry.

Their second marriage is a happier one as Mary Ann And Winston deal with the death of Ted Swirl at their reception, Mary Ann's son Eric coming out as gay, and various squabbles between family and friends. However, things change when a young girl named Blair begins sneaking around Halcoyn Hill. While Winston fears she is another gold digger he threatens to harm her to get rid of her, but Mary Ann insists on speaking to the girl whom she gets alone behind Halcoyn Enterprises. Blair reveals herself to be Winston and Mary Ann's daughter from their first marriage, and Mary Ann socks the girl with the revelation that she knew the second she saw her. While Blair offers to leave town, Mary Ann insists Winston know the truth. She gathers both of their families and reveals everything, how she discovered she was actually pregnant following her divorce from Winston but not wanting to halt his reunion with Mona she gave the baby up for adoption, and Blair informs everyone she only learned she was adopted when her father was on his deathbed. While Winston and Mary Ann are elated to have their daughter back, this secret greatly damages their marriage and Winston and Mary Ann separate with a brief rekindling at Eric's graduation they ultimately divorce a second time as he feels he can no longer trust her. Though after this the two reconcile a close friendship, and acknowledge that this time they got to see how their marriage would have worked out now that it was built on genuine love and trust.

Following this Winston's company would collapse, an event that coincides with Mona's return. While Winston is furious that he let his father's company fail, Mona tells him that he is now free from his father's grasp, though Winston doesn't see it that way. He and Mona come to blows over their previous marriages and it is revealed that Mary Ann brought Mona to town under the pretense that DeDe's pregnancy was dangerous, which it wasn't. Though they argue and seem distant, Winston makes it obvious that despite the past he still carries a torch for Mona, while Mona seems to have moved on now with her own company and a new fiance, Howard Trude. Yet at Candi's botched wedding to Ray Jordan the town is lit ablaze. While Winston goes back into the fire to secure Blair's safety Mona screams out for him to return safely, Howard is caught in the blaze and dies, with her fiance dead and her house burned to the ground Winston offers ona to stay with him at Halcoyn Hill. After thinking it over she accepts. Though shrill at first the close quarters get to the pair as they share various close moments like when Mona tells Winston that he is nothing like his father because she never would have wasted her entire life loving a man who was as diabolical as William. When Winston asks Mona if she still loves him, she simply states she will be moving out and leaving town. However, her plans are derailed by Alicia's death. She then remains in town for the funeral. After a night of reminicing about their children, Alicia and the past Winston and Mona share a long awaited kiss, again with her stating she intends to leave town.

Realizing he is back in love with Mona, WInston sets out to prove to her he loves her and that she has always been his one and only wife. However, at Candi and Jasper's wedding reception the following day Winston notices how Mona is not present with Ray informing his uncle Mona said she decided to go pack and leave while everyone was at the reception, without saying goodbye and believing it was less painful. Horrified she could be gone for good, Winston rushes back to Halcoyn Hill where he finds Mona coming out of the manor ready to go there he stops her, decalres his undyling and everlasting love and kisses her again. Though having put up a hard shell Mona surrenders to her love for Winston, saying he has been the only man who ever made her go weak in the knees. The two then passionately embrace again, reunited at long last. In the flash forward a year later they are not present but mentioned to be abroad visiting DeDe and Dorian on their honeymoon.


Winston has been married four times, to three women.

  • Mona Halcoyn (divorced) - After he discovered she slept with his brother, Ralph.
  • Mary Ann Werner (divorced) - After she realized he still loved Mona.
  • Mona Halcoyn (divorced) - After she stole a great deal of money, in order to keep a blaickmailer at bay.
  • Tanya Rockford (divorced) - After it is exposed that she was in cahoots with George Snyder, to ruin him.
  • Mary Ann Werner (divorced) - After she kept the existence of their daughter, Narcissa, from him.
  • Mona Halcoyn (married)

Winston has three children.

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