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- "Well, you might not be superhuman, Clark, but there's a reason that I thought you were the Good Samaritan." - Henry James Olsen, Identity
Jimmy visited Chloe Sullivan at the Talon after he found out that she arrived home from being away for a month. He told her that he did not want an answer to his proposal thinking it will destroy what they had, but Chloe gave him one anyway; she said yes, that she will marry him because he was perfect for her by being imperfect.
After moving with Chloe, Jimmy found a letter to Clark that Chloe had wrote six years ago and questioned Chloe's love for him and drowned his sorrows at the Ace of Clubs. There, he was seduced by Maxima and started to die from hormone overload. Jimmy almost fell off the balcony, but Clark caught him. Later at the hospital Jimmy explained that he doubted Chloe loved him and gave Clark her letter. Jimmy left the hospital two days later, and Chloe explained that her feelings for Clark were in the past. She also stated that her patience for Jimmy's insecurities were wearing thin. Jimmy is apparently at peace with the issue since Chloe said that Jimmy was her true love.
At Jimmy and Chloe's engagement party, they were both shocked after what Lois' proposal, which alluded to the fact that Jimmy might not be Chloe's soul mate. Hours later Chloe and Jimmy were kidnapped by a crazed jeweler and forced to prove their love with a torturous contraption that shocks a person if they lied. Chloe and Jimmy passed and were returned home. This prompted Jimmy to admit that he had been lying about his family since they met but Chloe said she understood.
Jimmy began to actively research a mysterious but unseen savior in the city, calling him the "Good Samaritan." Jimmy and Clark also investigated the destruction of the Ace of Clubs. He met Davis Bloome at his job at Metropolis General Hospital and asked if he could ride along with him so he can be first on the scene. Davis reluctantly agreed but that night, they were both attacked by a smoky blur until they were saved by the "Good Samaritan."
When the Samaritan saved Lois Lane right in front of Jimmy, he managed to take a photograph, identifying it as the "Red-Blue Blur." Not realizing the Blur was indeed Clark Kent, he asked Clark if he would help him write a story on the superhero, but Clark declined. Jimmy got his photo published and soon all of Metropolis learned about its new hero. Jimmy eventually realized that Clark was indeed the blur, but Clark enlisted the help of Oliver Queen to fool him into thinking he was wrong.
One week before their wedding, Chloe began to experience a severe bout of amnesia. When she forgot Jimmy, he turned to Clark for help. Jimmy took her to the hospital to get an MRI, but Chloe disappeared. She was returned home, still fearful and amnesiac, by Davis Bloome, who gave her a sedative. Jimmy was extremely concerned and insisted she go back to the hospital. She was returned home again by Clark, seemingly fully-recovered, and their wedding plans continued.
On their wedding day, a murderous creature crashed the wedding and kidnapped Chloe. Jimmy tried to fight him off, but Doomsday slashed him across the chest. Jimmy was gravely injured and suffered severe internal bleeding. He was transferred to Star City for emergency surgery, accompanied by Lois Lane. After a recovery period of five weeks, Jimmy was back on his feet and transferred to Metropolis General Hospital.
Upon his return home, it was revealed that Jimmy's recovery had been difficult. He suffered nightmares and severe lingering pain from his injuries and while in the hospital, he witnessed Davis murdering a man and tried to find proof on it, even sneaking into Davis ambulance. However, Davis injected him with a drug that caused him to hallucinate and although Chloe tried to support Jimmy, he felt that since she didn't believe him, she didn't trust him and would never stop choosing someone else over him. He refused to go home with her and told her that marrying her was the worst mistake he ever made, leaving a heartbroken Chloe in tears. He quit his job at the Daily Planet but not before leaving a file on Tess desk suggesting she investigate Davis.
Jimmy started to work at the Ace of Clubs and on his first day he asked Bruno Mannheim to ask Ron Milano for an advance on his wages. After Lois called him to take pictures of her as Stiletto for her story, Bruno noticed Jimmy's camera and recognized Chloe and Lois in the photos. He beat him up asking for information on Stiletto but Jimmy refused to tell him anything, then Bruno beat him unconscious and left him in the back room. When Bruno shot Clark who was protecting Lois, Jimmy awakened and tackled Bruno before Lois knocked him out. Then Jimmy and Lois help get Clark to the hospital to treat the bullet wound. Jimmy later went to meet a drug dealer, paying for the drugs using the counterfeit money that Bruno was making.
After Jimmy asked of Oliver for some money to buy more drugs, he turned him down and then Jimmy go to the Talon to steal money from Chloe but was stopped by Oliver, and then Davis attacked both of them from the shadows. Davis tied the two up in the basement of the Talon and Jimmy realized that Davis was the one who crashed his wedding and tore everything away from him. Davis was about to kill him but realized he meant too much to Chloe and she would never forgive him if he did. Before he went to the hospital for his injures, he told Chloe to stay away from Davis since he was a monster. Oliver then offered Jimmy a job at Queen Industries due to his efforts of seeing the good in people and to prevent him from becoming a drug addict.
Finally, Oliver had asked of Jimmy to go into Tess's office to use her tracking system to find Chloe and Davis' location. While he was there, he ran into Lois who was also there looking as well. Once Jimmy found their location using Tess' computer, he went straight there, only to find Clark with a Kryptonite dart in his back and no Chloe or Davis in sight. Clark finally admitted that Jimmy was right about him being the Red and Blue Blur after Jimmy saw Clark heal from his wounds.
Under Clark's instructions, Jimmy took Chloe and Davis to their "wedding present" which was a tower, and the two decided to make up after knowing the whole truth and they passionately kissed. Davis woke up from hearing this and stabbed Jimmy through the stomach with a pole. Before Davis could kill Chloe as well, Jimmy hurled Davis into a spike, killing him. Soon afterwards, Jimmy died in Chloe's arms and told Chloe that he loved her. At Jimmy's funeral, his parents, younger brother, Oliver, Dinah, Bart, and Chloe were seen there with Clark watching from a distance. Chloe gave Jimmy's trademark camera to his younger brother, saying he would've wanted him to have it.