On October 30, 2022, George Strait plays at the Grand Ole Opry in Nashville, Tennessee, at the Coal Miner’s Daughter: A Celebration Of The Life & Music Of Loretta Lynn. (Photo by Getty Images/Jason Kempin)

This week, George Strait is grieving the loss of two members of his close music family.

The country crooner shared on Instagram on Wednesday, March 20, the tragic death of his manager earlier that day. The two had been friends for even longer but had worked together for about 45 years.

He wrote, “Erv Woolsey passed away this morning,” at the exact moment. “He was unable to overcome the complications from a surgery. He fought valiantly and was a very tough man, but unfortunately, it was simply too much. We will always remember the time we spent together and will miss him terribly. He wrote, “Won’t be the same without him,” and included a picture of the two of them.

He had no idea that another of his close friends was also losing the war.

Mike Kennedy was Strait’s longtime drummer, who passed away after a car accident in 2018.