Grady Foley, an Australian native, arrived in Springfield in late 2006 on a mission. A professional hit man, Grady, using the alias Gillespie, was hired by Olivia Spencer to murder her nemesis, Ava Peralta. Weeks later, Olivia tried to call off the hit but was informed that it was too late. He had already killed her by using chloroform. Fortunately for Olivia and Ava, he was mistaken—Ava was still alive. Later, Olivia was put on trial for planning Ava's death, with Gillespie as a witness for the prosecution. However, the case was dropped when Ava testified that no crime was committed. Months later, while breaking into a boarding school over Christmas break, Gillespie encountered a lone student at the dorm named Daisy Lemay. The teenager took an instant liking to Gillespie who she called "G".

In early 2007, Daisy, a trouble maker herself and a drug user, took him to her mother's home which was coincidentally in Springfield. Days later, another Springfield resident hired Gillespie for his services—Alan Spaulding wanted Jonathan Randall eliminated. Unfortunately, Jonathan's wife, Tammy, overheard the plan and rushed to the meeting site to warn him. With a passed out Daisy in the back seat of his car, Gillespie was all set to run down Jonathan only to strike Tammy by mistake when she pushed him out of the way. Gillespie immediately ran off, leaving a passed out Daisy in the car. When Gillespie told Alan what happened, a furious Alan demanded that he leave town immediately. Meanwhile, Daisy found out what happened and asked him if he hit Tammy on purpose. However, instead of giving a direct answer, he encouraged her to leave with him. Afterwards, Gillespie learned that Tammy was dead but lied to Daisy that she had recovered. It didn't take long for Daisy's stepfather, Gus Aitoro, to tell her the truth. Meanwhile, while trying to recover his money, Gillespie was beaten to a pulp by Tammy's friend, Remy Boudreau. Suddenly, everyone knew his role in Tammy's death. As Gillespie recovered in Cedars, he received a visit from District Attorney Doris Wolfe who made him a deal—if he refused to testify against Alan, he would go free. Unfortunately, Doris double-crossed him and extradited him to Australia where there was a warrant out for his arrest.

The summer of 2008, Gillespie was released and made his way back to Springfield and Daisy. After filling her car with daisies, he approached Daisy. G expressed remorse for hurting Daisy and for killing Tammy. When he stated that Tammy's death haunted him, Daisy believed him. Mesmerized by her old boyfriend, Daisy brought him to Harley's to hide for a while since he was still wanted by the police. While hiding out at Daisy's mother's house, he came face to face with his own brother—Cyrus Foley! A bitter Grady blasted his older brother for abandoning him when he was young, Cyrus tried to explain that he did it for Grady's own good—so that Grady wouldn't be a thief like he was. Unfortunately, Cyrus realized that that backfired when he learned that Grady spent time in prison. It soon became apparent that Grady was a hardened criminal and Cyrus suspected that he stole the money that Cyrus had at Harley's. That same day, Cyrus saw Grady kissing Daisy, who coincidentally was the daughter of Cyrus's old lover, Harley. Recognizing that his brother had a mean streak, Cyrus warned Daisy away from him to no avail. Since the police were still after Grady, Daisy let him hide out at her grandmother Reva's storage garage and gave him money that she stole from Company. Soon after, Lizzie Spaulding learned that Grady was in town and offered to pay him off in exchange for his leaving town so that her grandfather wouldn't be implicated in Tammy's death.

Meanwhile, Cyrus finally learned about Grady's role in Tammy's death and when he confronted Grady about the type of man he had become, the pair was arrested. Though Cyrus was bailed out, Grady was left to stew, until Lizzie blackmailed a judge into setting a reasonable bail. While Grady was set to concede to Lizzie's demand that he flee town, Cyrus tried to convince Grady that he should stay and face the charges against him. Meanwhile, Daisy continued to defy her family by sneaking out to see him and she ultimately convinced Grady to go to the police a make a statement regarding Tammy's death. Later, desperate to get Grady away from Daisy, Reva tried to have him arrested for drug possession and slipped Jeffrey's pain pills into Grady's bag. It didn't take long for Grady to figure out what happened and he told Cyrus. Cyrus confronted Reva who gloated about what she'd done. Unfortunately, Cyrus had her confession on tape and used it to strong-arm Jeffrey into dropping the drug charges so that Grady could go out on bail. Weeks later, Grady was put on trial for Tammy's murder and convinced Daisy to lie for him. When Daisy testified that Grady never meant to kill anyone that night and she distracted him since she was ill, he was found not guilty.

Off the hook for Tammy's death, Grady settled in his life with Daisy. Weeks later, things hit a snag with the arrival of Daisy's former boyfriend, Rafe Rivera. When Daisy met with Rafe, who was on the run from the law, a jealous Grady falsely reported to the police that she was being held hostage. Meanwhile, Daisy told Grady that they needed to find jobs and talked to Dinah Marler about a job for Grady. Though Daisy continued to defy her family by staying with Grady, she continued to be concerned about Rafe--a fact that worried Grady. Not long after, Cassie learned that Grady was the one who called the cops on Rafe and told Daisy. Upset, Daisy broke things off with Grady. A vengeful Grady went to Cassie's but was intercepted by Cyrus who warned him away. The same day, Grady got a visit from Dinah who was looking for Cyrus for a job. Grady told Dinah that he could do anything that Cyrus could. Though skeptical at first, Dinah quickly relented and hired Grady ranting that she wanted her brother, Bill, hurt so he'd realize how much he needed her. So, donning a mask, Grady attacked Bill. Unfortunately, the person who wound up taking care of Bill was Lizzie. Finally, Dinah gave Grady a new assignment—break up Bill and Lizzie. In the meantime, Dinah was finding herself physically attracted to Grady and the feeling was mutual. However, Dinah was adamant that they stick to the business at hand. Unfortunately, the plot went nowhere and seemed to backfire when Lizzie and Bill were set to deliver a joint presentation with some influential investors.

Knowing that Dinah wanted Lizzie out of the picture, Grady took it upon himself to kidnap Lizzie and kept her tied and blindfolded in the basement of WSPR. He also disguised his voice so she wouldn't recognize his accent. When Dinah found out, she was appalled but kept quiet out of fear of being implicated. Intrigued by each other, Dinah and Grady soon made love. Soon after, Grady sent Bill a ransom note. Though Lizzie almost succeeded in escaping when she cut herself loose with her keys, she was stopped by Grady before she was able to remove her blindfold. Before being tied up again, Lizzie was able to scratch Grady with her keys. Later, Grady went to the ransom drop but before he was able to get the money, he heard a cell phone ring—alerting him that Bill wasn't alone. Grady ran off. Unsettled, he called Daisy just to hear her voice but Daisy told him that she couldn't save him and ended the call. Uncertain about how to proceed,

Grady decided to transport Lizzie off to transport her to another location. While he was getting her water, Lizzie, still blindfolded, bolted from the van and ran off and fell right into a deep hole. As Grady helped her out, he accidentally fell in the hole himself. Now free, Lizzie was able to untie herself and ran off. However, having connected some Grady, she quickly returned and offered to help him out of the hole if he took off his ski mask. Though incredibly reluctant, Grady eventually agreed. Luckily, before Lizzie got a chance to see his face, she was grabbed from behind and tied up again. Grady's savior was Cyrus who pulled him from the hole and. blasted him for the idiotic scheme that he thought Dinah concocted. Grady told Cyrus that it was his idea and was hurt that Cyrus didn't think he could get away with it. Later, Grady transported Lizzie to an abandoned factory. He was soon discovered by Bill who knocked a masked Grady out and rescued Lizzie. During the rescue attempt, Bill crashed the van he was driving and was left comatose.

Though Grady was poised to smother Bill with a pillow since he feared that Bill saw him during the rescue, he couldn't bring himself to do it. In the meantime, Daisy unexpectedly befriended him. Knowing that something was bothering him, she asked him to open up about and kissed him. Though Grady was tempted to talk, he kept quiet but accepted Daisy's offer of reconciliation. Later, seeing an advantage, Grady went to Alan and admitted that he was the one who kidnapped Lizzie. Grady then proposed that they frame Bill for the crime since that would secure Grady's freedom and get Bill out of Lizzie's life. Appalled, Alan held a gun on Grady and tied him up and planned to turn him in to the police, but later, agreed to Grady's plan. Soon, the ransom notes and a jacket like the one Grady was wearing were planted in Bill's possession. The plan worked and as soon as Bill woke up, he was arrested for Lizzie's kidnapping.

Meanwhile, Daisy's best friend, Ashlee, tried to convince Daisy that Grady was a bad guy. However, despite all of her pleas, Daisy continued to defend Grady. Later, Grady rescued Ashlee from a mugger. From that point on, Ashlee softened towards Grady. The Cooper family softened as well and permitted Grady to enter the family restaurant. However, Ashlee still didn't want her best friend dating a loser and, near the end of the year, got him a job at the mayor's office since her mother, Doris, was the mayor. Doris knew Grady's history and decided that she could use a man of his questionable tactics on her staff. In 2009, Grady seemed off the hook for Lizzie's kidnapping since Bill could not remember any of the events surrounding it. Unfortunately for Grady, Daisy believed in Bill's innocence and gave him the number to a hypnotherapist who might be able to retrieve his memories. Grady gave the man's number to Alan and told him to impede Bill's progress. Though the hypnotherapist declined Alan's bribe, he was still unsuccessful in retrieving Bill's memories. Meanwhile, weeks later, Daisy was rocked by the death of her uncle, Coop Bradshaw. Though Grady wanted to be there for Daisy, Daisy decided that it would be inappropriate and asked him to stay away.

Later, Bill overheard Grady argue with Cyrus about his role in the kidnapping. After an altercation, Bill slipped out and went to Lizzie's. Luckily, Cyrus and Grady got to him first and kidnapped him. In the meantime, Coop's death was especially hard on Buzz who blamed Alan. Wanting revenge, Buzz asked Grady to finally admit in court that Alan hired him to kill Jonathan. Though Grady was reluctant, Daisy was able to persuade him to help her family. Again, Lizzie bribed Grady to leave town without testifying. At Cyrus's suggestion, Grady agreed to leave town in exchange for 1 million dollars. The evening that he got the money, Grady got a message to meet someone at the edge of a cliff. That man who called Grady turned out to be Phillip Spaulding—Alan's son and Lizzie's father. Grady proposed a deal—he would send Alan away to prison if Phillip forgot about the kidnapping. Grady then revealed that Alan found out about the kidnapping and hired him to frame Bill. Grady also revealed that Dinah was the mastermind behind the kidnapping. When Grady casually threatened Lizzie, Phillip blew up and threw Grady off the cliff to his death. However, Grady's body was never found since he had fallen into the thick underbrush and most of Springfield believed that he simply left town.