WWE Hall of Famer Jeff Jarrett has shared some details about a personal moment involving global music star Taylor Swift, recalling how the Fearless singer once performed a three-hour private Christmas concert for his family while his late wife was battling cancer.In a recent interview with TMZ Sports on August 30, 2025, Jarrett narrated the incident, saying that the concert was held in December 2006 at his family home in Hendersonville, Tennessee. His first wife, Jill Gregory, was battling breast cancer at the time, and the family was going through a challenging time.Taylor Swift’s early ties to the Jarrett familyIn the interview with TMZ Sports, Jeff Jarrett remembered the Christmas of 2006 when his late wife Jill Gregory was very sick with breast cancer. Only five months later, in May 2007, Gregory passed away, so the holiday party was the last time the family enjoyed Christmas together.“It was Christmas of 2006. My first wife [Jill Gregory] was really ill with breast cancer. She passed away about five months after this, so she was really ill,” Jarrett recalled.Taylor Swift herself was only 17 at the time and in the early phase of her career following the release of her self-titled debut album, and spent significant time with the Jarrett family. The wrestler described how the singer-songwriter would often come to their house and make cookies with his daughters and even assist in taking care of the children.Jarrett remembered that it was one of Taylor Swift’s friends who had suggested she visit the family home, an invitation which was received with joy by his daughters.“Obviously, like every little girl in America, my daughters were big Taylor fans, and her songs had just kind of broke, but she was a hometown girl,” Jarrett said.Taylor Swift at The Eras Tour in Toronto (Image via Getty)The wrestler recalled how Taylor Swift spontaneously gave a three-hour performance during the holiday season. It was originally in front of just a few members of the family, but eventually expanded to almost 45 as the news travelled throughout the neighborhood and among friends.“By the end of the afternoon, Taylor played about three hours,” Jarrett mentioned.He went further to state that he was already familiar with Taylor Swift and her family because they were from the same hometown, and had seen the Swifts around town.“She kind of bonded with the family, specifically with the girls,” Jarrett shared.When Jarrett was questioned whether Swift was the babysitter of the family, he explained that she was not on the “payroll,” but loved the children and used to hang around with them.“But what a very cool relationship that developed. When my wife passed away, Taylor would come around, and was really good with the girls,” Jarrett said.Jill Gregory’s illness and passingJill Gregory, Jeff Jarrett’s first wife, was diagnosed with breast cancer in the mid-2000s. She and Jarrett had gotten married in 1992 and had three daughters together. Gregory continued to receive treatment, but her condition deteriorated and she passed away on May 23, 2007, at the age of 37.The private concert Taylor Swift gave was in the last months of Gregory’s life, when the family was coping with her illness and its impact. Jarrett mentioned how the performance became a significant memory for his children, who were still young during the time of their mother’s passing.The incident also showed how close the Jarrett family was to Taylor Swift at that time. Both resided in Hendersonville, Tennessee, a city located near Nashville, where Swift was beginning her professional music career.Stay tuned for more updates.