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Clint Black at Wal-Mart
I was a young girl in 1995 when Clint Black was at Wal-Mart in Harrisburg, IL. We all received a ticket. Luckily my number was called to go up and meet him. I won a shirt and he signed it.
A Clint Black signed photo is worth about $50. Your shirt would probably be worth about that. Signed apparel isn't as easy to sell as a photo though, especially if the item is inscribed. It is probably worth more to you than it would be to anyone else.