Country Music Icon George Strait Mourns Two Heartbreaking Losses in His Inner Circle
Country music legend George Strait is enduring a heartbreaking week marked by the loss of two deeply important people in his life. On March 20, 2025, Strait took to Instagram to share the devastating news that his longtime manager and dear friend, Erv Woolsey, had passed away.
“Erv Woolsey passed away this morning,” Strait wrote in the emotional post. “He couldn’t beat the complications that followed his surgery. He gave it everything he had—he was one of the toughest people I’ve ever known—but this time, it was too much. I’m going to miss him more than words can say. Life won’t be the same without him.” The message was accompanied by a poignant photo of the two men together, a testament to their bond that spanned more than 40 years.
Woolsey had been at Strait’s side for 45 years, not only managing his career but helping shape it into one of the most celebrated journeys in country music history. Their relationship was more than a professional alliance—it was a brotherhood forged through decades of loyalty, trust, and shared success.
Strait’s sorrow runs even deeper as memories resurface of his late drummer and close friend, Mike Kennedy, who tragically lost his life in a car accident back in 2018. Though time has passed, the pain of Kennedy’s death lingers—especially now, as Strait faces yet another personal loss from his close-knit musical family.
For George Strait, this moment isn’t just about mourning—it’s a powerful reminder of how quickly life changes, even in the strongest relationships. While the world continues to celebrate the King of Country’s unmatched legacy, Strait himself is quietly navigating a chapter filled with grief, reflection, and the deep ache of missing those who helped shape his life and music.