Country legend George Strait is mourning the loss of two close members of his musical family. On March 20, 2024, he announced on Instagram the passing of his longtime manager and friend, Erv Woolsey, who had worked with him for over 45 years.

“Erv Woolsey passed away this morning,” Strait wrote. “He fought valiantly through complications from surgery, but it was just too much. Won’t be the same without him.” He shared a heartfelt photo of the two together, honoring their decades-long friendship.

Tragically, Strait also remembered another deep loss—his longtime drummer, Mike Kennedy, who died in a car accident in 2018. Kennedy had been a vital part of Strait’s band and sound for years.

As the country icon continues to perform and connect with fans, these personal losses serve as a reminder of the deep bonds formed behind the music—and the enduring grief when those bonds are broken.