Derby 150

May 01, 2024

With the running of the 150th Kentucky Derby coming up Saturday, I thought I’d do a little reminiscing about the 11 Derbies that I shot for either the Louisville Courier-Journal or the Lexington Herald-Leader, as well as a few corporate gigs that I did at the Derby for Xerox.

I shot my first Derby for the Herald-Leader in 2004, which was the year of Smarty Jones. I didn’t work at Churchill Downs that year, but I covered the Derby at Keeneland in Lexington. Turns out, that place is packed each year for the Derby, and is a great atmosphere if you don’t want to go to Louisville.

The following year, I made it to Churchill and covered the infield during the day, and then the First Turn during the race for the Courier-Journal. The CJ does a piece each year in their print edition called “Around the Track,” which is a series of panoramic photos that show where each horse is during the race, and my part was at the First Turn. Jockey Mike Smith and Giacomo crossed the line at 50–1 odds in 2005 and came within a few feet of me as they made their victory lap back to the winners circle.

I remember it was so hot that year as I sat at my spot on the track, waiting for the race to start, that I paid some kid $5 to go get me a screw top 20 ounce Pepsi. After I drank it, I thought to myself that I may never have an opportunity to sit on the track and photograph the world’s greatest horse race ever again, so I scooped up dirt from the track into the empty Pepsi bottle to take home as a souvenir. Turns out, I made it back to the First Turn nine more times.  

One of the most interesting moments of my entire career came in 2008. Just seconds after Big Brown won the Derby, he was making his way back to the winner’s circle, and instead of staying in the middle of the track as NBC’s reporter Britney Eurton interviewed jockey Kent Desormeaux, Big Brown pushed the outrider to the outside rail. He was literally on top of me, as I pushed as hard as I could against the chain link fence behind me to get enough separation for a shot. Technically, it wasn’t the greatest shot ever, but the fact that the Kentucky Derby winner was within inches of my lens, it was a pretty damn good shot!

But the joy ended there, because once Big Brown got past me, I saw that another horse was down on the track, back toward the back stretch. It was Eight Belles. She had to be euthanized on the track for a broken leg. I had a very graphic photo with the track’s vet pulling off the syringe cover with his mouth as he stood over top of the filly. At first, the CJ refused to run it all, which kind of confused me, but eventually they buried five of my photos in the online edition. I had mixed emotions about that because it was news and it happened in front of 158,000 people and on national television. But, in retrospect, it was probably too much reality for the general public, especially after Barbaro had died just two years earlier. Channel 36 in Lexington did an interview with me that explains it more.

I thoroughly enjoyed my time covering the Kentucky Derby. It was never about the money because I only made $250 for the day, which was a great day-rate for newspapers, but was only a fraction of what I make for the day as a corporate freelance photographer. I always loved the atmosphere of
the Derby because it was such a cultural paradox. In the grandstands you could see dresses, suits, cigars, and hats, that literally cost thousands of dollars, or you could go to the infield and some girl in a tank top and a pair of cut off jeans would flash her tits…just for the heck of it! You never knew what to expect in the infield. 

I worked a couple of years for Xerox in addition to the CJ and made it up to the fringes of Millionaire Row. While there, I once stood in a buffet line and talked with NFL legend Terry Bradshaw, and once got a glimpse of Queen Elizabeth and Prince Phillip. But for the most part, I enjoyed the opportunity to photograph and document The Greatest Two Minutes in Sports, with ordinary people on all sides of the economic spectrum. As long as I live, I’ll never forget what it felt like to stand on the dirt, on the track of this famed venue, listening as they sang My Old Kentucky Home each year. It was one of the greatest treasures of my career! There’s nothing else like it. Weep no more my lady!!!

Eventually, my kids grew up and started going to prom, which was always on the first Saturday in May at their school. As much as I love photography, it’s like a mistress that is constantly pulling me away from my family. I decided that I had been there and done that with the Derby long enough, and that it was more important to be a Dad in Richmond than it was to be one of hundreds of photographers working the Derby in Louisville. With that, I shot my last Derby in 2014, and I now enjoy watching it on my couch, in the comforts of my own home, with a cold beer that didn’t cost $12!

And they're off....


Photo by Tim Webb

2014 First Turn

Photo by Tim Webb

My first First Turn, 2005


Jockey Mike Smith celebrating after winning the 2005 Kentucky Derby with Giacomo.

I still have that Pepsi bottle with dirt from the track in my office.

Photo by Tim Webb EQUINEEQUINE EQUINEEQUINE EQUINEEQUINE EQUINEEQUINEStanding at the rail, covering the Kentucky Derby for the Louisville Courier-Journal, May 2006.

The Eastern Progress Photo Editors Club working the Derby in 2009. Left to right, Kevin Martin (2000), myself (1991), Mark Cornelison (1989), & Rob Carr (1986).


Kentucky Derby 2011. I picked up Xerox as a client for Oaks and Derby and got to spend a little time in the suites.

Working for Xerox in 2010.

EQUINEEQUINEWorking the infield during the Kentucky Derby, 2007. Working the infield.
Standing with the Spires, Kentucky Oaks, 2010. Photo by Dan Dry

EQUINEEQUINEBig Brown inches away from my camera lens, just minutes after winning the 2008 Kentucky Derby.
Big Brown stuck his nose in my lens just a few seconds after winning the 2008 Kentucky Derby.

EQUINEEQUINEFilly Eight Belles goes down and is euphemized near the back stretch, after breaking her two front legs, after placing in the 2008 Kentucky Derby. Eight Belles went down during the 2008 Derby.

Photo by Tim Webb   Photo by Tim Webb
The parade of owners and trainers before the race is always a specitale at the First Turn!

Photo by Tim Webb Photo by Tim Webb Photo by Tim Webb Scenes from the infield at Derby 139.
May 4, 2013
Eric Vernenberg, front, and Eric Doolittle, slide on a tarp in the infield, during Derby 139.
May 4, 2013
EQUINEEQUINE EQUINEEQUINE EQUINEEQUINE EQUINEEQUINE EQUINEEQUINE EQUINEEQUINE EQUINEEQUINE EQUINEEQUINE EQUINEEQUINE EQUINEEQUINEPhoto by Tim Webb Calvin Borel celebrates with Super Saver after winning the 2010 Kentucky Derby, in a mudfest, seen below. EQUINEEQUINE This guy from Chicago got creative with sneaking liquor into the infield. Is it a loaf of bread, or is it a pint of bourbon? Hard to tell!


The media center was the largest that I have ever worked in, with about 300 credentialled photographers. But you notice I'm up top looking down on the commoners, ha!, with the Courier-Journal, the Herald-Leader and the Associated Press. And the food there was freaking awesome!!!
Two Louisville Courier-Journal legends here. Michael Clevenger, left, and the venerable Bill Luster, right. 

EQUINEEQUINE Photo by Tim Webb Self Portrait My last view from the office, 2014.

My 2008 Interview with Channel 36 about the Eight Belles tragedy. 


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