Rolex Air King Winner: Grady, July 2025 - Wolf Watch Club

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Rolex Air King

Grady Hill, winner of the Rolex Air King #5

Grady Hill

United States

Winner Story: Grady Hill & the Air King

Grady Hill never thought a Sunday morning would change his watch collection forever.

“I like fully mechanical watches—exhibition backs are really cool. How did somebody figure out the math to make all this work?” Grady says, a software engineer by trade and lifelong lover of ticking gears.

He’s been in raffles before, but this was different.

“It’s my first drawing. It’s a big shock,” he laughs. “I liked the limited number of available entries. I liked the watch.”

The Air King caught his eye, but it was more than just the piece itself.

“When I was a kid, I had a Bulova self-winding… had it for several years and then lost it. I graduated from college and bought myself a nice mechanical watch and used if for years.”

He’d seen The Time Teller before, “I have dealt with Jory in the past, I felt good about his recommendation. He wouldn’t support someone he shouldn’t. I like his take on reused watches, gets you to take a broader look at everything. He gives his opinion, no sugarcoating.”

On a whim, Grady picked up his entries.

“I bought three entries on Saturday morning. I occasionally will play a lottery, Powerball maybe. But not recently.”

Then came the competition: “On Sunday, I was listening to the competition live and I was really happy. I was alone but I was feeling good. Happy.”

Now, Grady’s got an Air King on his wrist—a mechanical wonder, a childhood dream rekindled, and a new story to tell.