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Gary was the troubled son of Eddie and Anna Windass and often hung round with his Uncle Len who was the source of his scrapes. When the Windass family refused to pay for a kitchen fitted by Joe McInTyre Joe's daughter Tina and her boyfriend David Platt tore the kitchen out and set it on fire.. Gary and Len then destroyed the Platt kitchen in retaliation. When Eddie and Anna rented a flat from Jerry Morton Gary became David's next door neighbour.

Gary helped his Uncle steal tools from Joe and repeatedly taunted David over his dodgy past. The animosity eventually caused David to hit Gary and Gary to respond with a vicious assault. David tried to make Tina lie in court and say Gary had thrown the first punch but she decided to tell the truth leading Gary to be found not guilty.Following this David Stole Bill Websters tools then provided Gary with a false alibi. Knowing that Gary needed money David staged a burglary at his grandmother Audrey Robberts house hoping to get Gary arrested which he achieved by calling the cops, though before Gary's imprisonment he was able to exact some revenge on David by telling the cops of David's involvement resulting in David being shunned by street residents.

After being released from prison Gary encountered a battered David and implied he had been responsible for arranging the beating using it as a warning for David to stay out of his way in future.After feeling guilty over disparaging remarks he had made about the army Gary was inspired by the stories told by David's grandfather Ted Page to enlist.

While in the army Gary became close with fellow squadie Quinny. While on leave Gary had a brief romance with Izzy Armstrong.When Quinny was killed trying to save Gary he began to experience PTSD and was discharged from the army after he assaulted a cop, while on a night out with David. When Anna and Eddie fostered Faye Butler. Gary helped her warm to her parents. Gary's PTSD caused the relationship to collapse as he was paranoid Izzy would be endangered if she left home and even tried to keep her from doing so.Gary and Izzy later got back together and he worked as a laborer for her dad Owen

.After suffering a miscarriage Izzy and Gary decided to use a surrogate and hired Tina McIntyre. There some initial issues when Tina gave birth to Gary's son Jake as Tina didn,t want to give the baby up but ultimately she let Gary and Izzy have him.after Gary confronted Owen's business partner Pat Phelan for harassing Anna, Phelan goaded him about his mother causing Gary to lose his temper and knock Phelan out with a wooden plank.Phelan then used this to blackmail Owen and Gary into finishing the project they were working on for no-profit and only released them after Anna agreed to sleep with him.

Gary Was largely blamed for the financial situation Which put a strain on his relationship With Izzy. Gary cheated on Izzy With Alya Nazir. Izzy ended the relationship after learning of Gary's betrayal. Alya ended the relationship due to the disapproval of her father Kal. Desperate for money Gary attempted to steal from local cafe owner Roy Cropper who assaulted him with a baseball bat.Gary,s guilt about stealing from someone he knew caused him to lie about the amount of times Roy hit him.Gary later  went to see Roy in order to apologise and expressed a desire to change his ways

.Roy then gave Gary employment. Things began to get better for Gary as he rekindled his relationship with Alya and her family came to accept him with her grandfather Sharif even giving him a share in his gym as an early wedding present. After Kal died in a fire a grief stricken Alya attempted to initiate sex with Gary who (knowing that it was forbidden by his Islamic faith and seeing how vulnerable she was) refused to do anything. Alya then slept with his friend Jason Grimshaw, when Gary learnt about this he temporarily left the street.

When he returned Gary got friendly With Jason's ex Eva Price in a deliberate attempt to get under Jason's skin. Gary discovered that David's niece Bethany Platt Was being bullied and tried to help her through it. Bethany,s mother Sarah suspected Gary of seeing Bethany but was touched to learn the truth. Gary saved the life of David's daughter Lily as David's reckless driving over his desire to kill his wife's murderer Clayton Hibbs resulted in the car almost falling on top of her.

David's scheme for revenge also resulted in Anna being burnt. Gary confronted David at Audrey's Salon and assaulted him. Gary began seeing Sarah and the Platts were surprisingly quick to accept him into the family. Gary (and the rest of the family) were disgusted by Bethany's relationship with Nathan Curtis as she was many years her junior but their attempts to warn her fell flat and Nathan successfully groomed her.

Gary began doing security work in the Ukraine in order to pay for Jake's speech therapy but became increasingly stressed and impregnated Phelan's daughter Nicola Rubinstein as a result. David revealed Gary's betrayal to Sarah causing her to leave him. Gary knew that Phelan had manipulated Seb Franklin into thinking Anna pushed him off a ladder and bundled Seb into a taxi so he would testify in Anna's favor but this evidence was rejected when Phelan's wife Eileen found evidence of Gary's intimidation. Gary also discovered Bethany working in a strip club and tried to get her to come home only for her to have the bouncers beat Gary in revenge for his infidelity. Sarah visited Gary and the pair began to mend their differences ultimately leading to a full reconciliation.

Gary took part in a charity boxing match in memory of Luke Britton and was pitted against David after Tyrone Dobbs backed out. David beat Gary with in an inch of his life and left him hospitalised. Gary was surprisingly understanding as he suspected David was suffering PTSD over the death of his wife Kylie. Gary told David not to push others away and defended him in court which helped get him off on a suspended sentence.

Gary also tracked Phelan down to kidnap him and bring him back to the street. After Phelan escaped he took Gary prisoner but Anna arrived to save her son by killing Phelan.

After getting in debt with loan Shark Rick Neelan Gary sabotaged the roof of the factory underworld (which caused the death of Rana Habeeb and the mental breakdown of Carla Connor) in an attempt to pay Rick off. Gary's conscience led him to disobey Rick's orders as he backed out of conning an elderly woman and Saved Vicky Jefferies from Rick's thug Shannon. After being tricked into thinking Rick had Sarah prisoner Gary went out to the woods where he fought and killed Rick.

When Gary got back to Sarah he learned she had begun a relationship with Adam Barlow and furiously slammed her against a wall. This situation led to a bitter rivalry with Adam and Gary. Gary took over Rick's business and began intimidating debtors just like Rick used too. Gary also set up Derek Milligan as a fake business investor in underworld in order to make more money. Gary was troubled by guilty feelings over Rana,s death  and paid for her Wife Kate Connor to go on a vacation.

Gary Viciously assaulted Ryan Connor as he owed him money but presented himself as a hero who had rescued Ryan from muggers. He also used Ryan's injuries to warn Derek against making advances towards Izzy.

Gary also established a friendly raport With Maria Connor after paying for her shopping.Gary and Maria became closer when he saved her son Liam from a small fire after hearing a smoke alarm.

though the affection seems to be genuine Gary did enjoy using it to mock Sarah and make her jealous.Gary's relationship with Maria caused her ex boyfriend Ali Neeson to become jealous however Gary worried Ali would try to take her back and after Ali failed to properly examine Emma Brooker Gary took advantage of the situation to cause drama between Ali and Emma's father Steve McDonald,Gary made a formal commit to Maria after he saw her kissing Ali and demanded to not be messed around.he hired a private investigator and discovered Ali,s drug addiction hoping to use it as leverage.Ali was warned off by Gary and became suspicious when a concerned Ryan warned him not to cross Gary.Ali  got possession of the book Gary used for his loan Shark business  and attempted to tell Maria however Gary revealed he had stolen Ali,s phone.on the phone there was a message that contained Ali,s friend Toyah Battersby talking about his drug addiction.Gary used this to Make Ali return the book and demand he stay away from Maria.as punishment for telling Ali about the attack Gary told Ryan the interest in his debt was returned and it was now doubled.Gary Was  ecstatic to learn Maria  Was pregnant.Ali became concerned for her and told  her about Gary's crimes.When Maria confronted him Gary told her the only true accusation levied at him was his attack on Ryan Which Was done after the lad stole money from him.Maria bought this and Gary convinced her Ali Was just a jealous Ex trying to drive them apart.Gary also reminded Ali that he knew about his drug addiction.When Ryan requested he be allowed to do a few Jobs to pay of his debt Gary chose to agree.He had Ryan make a delivery to Lennie(the private investigator who uncovered Ali's drug addiction) and secretly instructed Lennie to press for information about him.When Ryan Kept quiet Gary was impressed.He rejected Ryan's attempt to pay off half his debt and told him he would soon have use for him in the future.after discovering that Derek Was trying to sell underworld behind his back Gary Forced him to buy it of him for one penny and went as far as to threaten Derek's family if he crossed him again.Gary attended the party for Underworld's return  but got into an argument With Sarah's brother Nick Tislley Who had learned of Gary's assault on Sarah from Adam.Gary revealed that he now owned the property after Izzy Made a comment regarding Something Derek Said.Gary then lied to Maria about how he acquired the money.Gary Taunted Nick and Sarah that he planned to raise the rent every time they disrepected him.as punishment for causing Maria to doubt him Gary chained Derek Up causing him to miss a flight to Disneyland and lose all contact With his family.Derek later acquired a gun and went into the rovers return to threaten people with it.Gary confronted Derek  and taunted him.Gary ran off and the men ended up in Winter Wonderland.Gary Warned Sarah and her family to hide as he wished to Keep them safe from Derek's wrath.Gary Was also able to return Sarah's son Harry (who had ran off) to his mother protecting him from being caught in the crossfire.When Gary saw Derek on the balcony and it seemed like he may shoot at Maria He ran up.When the police arrived Derek began to fall off.Gary tried to save him but was unable to do so.Gary suffered terrible guilt as his actions had Derek to accidentally Kill Robert Preston and Wound David's wife Shona Ramsey.After these events Ali reported Gary to the police.Gary confessed his crimes to Maria but talked her into forgiving him and ended his loan Shark business.Gary then began threatening Sarah and Nick with eviction of they didn't pay the rent though evntually realised the error of his ways.After Maria miscarried Gary was distarught and later earned the miscarriage was a result of measels Maria caught from the son of Adam's uncle Daniel Osbourne.Gary tried attacking Daniel but was dragged away by Adam who threatened to call the cops on him if he ever hurt his uncle again.Gary also refused to give a loan to an old client when asked.

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