Heartbreaking for George Strait

Heartbreak for George Strait as He Mourns the Loss of Two Close Friends

Country music legend George Strait is facing a painful week of loss after saying goodbye to two cherished figures in his inner circle. In an emotional post shared on Instagram on March 20, 2025, Strait announced the death of his longtime manager and close friend, Erv Woolsey.

“Erv Woolsey passed away this morning,” Strait wrote. “He couldn’t overcome complications from surgery. He fought hard—he was as tough as they come—but this time, it was too much. I’ll miss him terribly. It won’t be the same without him.” The heartfelt caption was accompanied by a photo of the two men, underscoring the deep bond they shared over more than four decades of friendship and professional collaboration.

Woolsey had managed Strait for 45 years, guiding him through a historic career that reshaped country music. Their partnership went far beyond business—it was a brotherhood built on mutual respect and loyalty.

Strait’s grief was compounded by the memory of another dear friend and bandmate, Mike Kennedy, his longtime drummer who tragically died in a car accident in 2018. Though several years have passed since Kennedy’s death, the loss still casts a shadow during moments like this, when another piece of Strait’s musical family is lost.

For George Strait, this isn’t just a period of mourning—it’s a poignant reminder of how fleeting even the most enduring connections can be. While his fans continue to celebrate his legacy and music, Strait himself is navigating a quieter, more personal chapter of sorrow and remembrance.