Country music legend Alan Jackson has a brand-new reason to smile — his family has officially grown again with the arrival of his second grandchild. On June 20, 2024, Jackson’s oldest daughter, Maddie Jackson, welcomed her first child, a baby boy named Wesley Allen Smith, with her husband, Connor Smith. The couple shared their joy with fans through a series of tender photos posted on social media, showing their newborn son swaddled in a blanket and cradled in their arms, as well as sweet moments with their growing family of four.
For Alan and his wife, Denise, the birth of Wesley is another cherished milestone, deepening the love and bonds that have always defined the Jackson household. The couple, who have been married for more than four decades, are now proud grandparents twice over. Their younger daughter, Ally Jackson Bradshaw, welcomed a son, Jackson Alvie Bradshaw, in December 2022, making Wesley the newest cousin in the family.
Maddie’s journey to this joyful moment has been one of resilience and faith. She tragically lost her first husband, Ben Selecman, in a 2018 accident, an experience she later detailed in her deeply personal book Lemons on Friday, which chronicles her path through grief toward healing and hope. Finding love again with Connor Smith, Maddie has embraced this new chapter with gratitude, often sharing glimpses of their life together on social media.
Alan Jackson, who revealed in 2021 that he had been diagnosed with Charcot-Marie-Tooth disease, has spoken often in recent years about the importance of family and slowing down to savor life’s most precious moments. The arrival of his second grandchild comes during a period when the country star has scaled back his touring schedule to focus more on his health and loved ones. “These little ones bring a different kind of joy,” Jackson has said. “You just want to soak up every second.”
The Jacksons are not the only country family celebrating baby news this year. Fellow stars Jessie James Decker, Gabby Barrett, and Kane Brown have also recently welcomed new additions to their families, adding to a wave of joy sweeping through Nashville.
For Alan, whose career has been defined by heartfelt storytelling and songs about love, home, and faith, moments like these are a reminder that the greatest hits are often the ones lived offstage — in the quiet joy of holding a new grandchild, surrounded by the people who mean the most.