George Strait‘s longtime manager Erv Woolsey has died.

The Country Music Hall of Fame artist shared the news on social media, adding that they worked together for about 45 years. Woolsey was “most importantly my friend for even longer.”

“He was a very tough man, and fought hard, but sadly it was just too much,” Strait says. “We will miss him so very much and will never forget all the time we had together. Won’t ever be the same without him.”

While Strait was Woolsey’s most tenured artist, he was hardly the only superstar he worked with.

The one-time record label head also helped Freddy Fender, Donna Fargo and Jimmy Buffett at various points in the ’70s and ’80s. He first saw Strait perform at a club he owned with his then-wife, and from there, the professional and personal friendship blossomed.

Strait was signed to MCA on a one-single deal in 1981. The song was a Dean Dillon co-write called “Unwound” that Johnny Paycheck couldn’t record on account of being in jail. Forty-three years later, he’s still with MCA Records.

Sixty No. 1 singles, multiple Entertainer of the Year wins and induction into the Country Music Hall of Fame are among the singer’s crowing professional achievements.

Woosley worked with new artists like Ian Munsick and Tyler Halverson until the very end.