I started collecting the Woodford Reserve Kentucky Derby commemorative bottles a couple years ago and was really excited to see who they chose for this years logo. Local artist and former jockey Tom Chapman was chosen and I think he did a great job, one of the better bottles I've seen over the years. Here it is:
Tom says that the jockey in red is based on him from his racing days.
I stopped by Tom's gallery which is near my house and had him sign my newly purchased bottle, he hadn't received his bottles from W.R. yet so he was pretty happy to see it. He also has limited edition prints of the artwork for sale as well. Here's a link to Tom's site (I don't think he has the Woodford bottle art on there but you can contact him if interested):
http://www.chapman-arts.com/showcase.html