Each year's poster depicted a different image or feeling associated with the Travers. 1987's was a picture of the clubhouse, another year flaunted a beautiful woman in a big red hat, one poster featured a jockey, another showed the paddock area of the track and 2008's poster re-captured the previous year's dramatic finish between Street Sense and Grasshopper.
To entice his imaginative juices, Montgomery has settled into a sort of routine.
"I spend a lot of time at the track. I try to get up very early in the morning and watch the horses work out because that's a really special part of Saratoga. I try to get over on the weekends because that's when the biggest crowds are there, and I'll look around and see if anything catches my eye," said Montgomery, who said it takes about a month and a half to complete each poster.
Up until 1999, the Travers posters were done by silk screening. The materials used in that process are very unhealthy, though, so Montgomery switched over to drawing them by hand and finishing them on the computer.
"I draw every little piece of dirt by hand and then fill in the colors on the computer," said Montgomery.
For the 2011 poster, Mongtomery said he's going to try to return to his roots.
"I'm very serious about trying to go back in the other direction for this next poster and make every effort to silkscreen," said Montgomery.
Since his art has become the face of the Travers, Montgomery has found himself involved with horseracing in yet another capacity.
"I was asked years ago to create book covers for a murder mystery writer, Dick Francis. He is a very famous fellow, was jockey to the Queen of England and a fighter pilot in Great Britain during WWII. He suffered an injury that put him in the hospital for quite some time, during which he tried his hand at writing," said Montgomery. "He's written more than 44 murder mysteries that all have to do with racehorses. I love doing those covers."