Work is, well, a lot of work. But great performance can lead to great rewards. For the end of  the fiscal year, our region ran a competition among managers for new business sales. The top performing manager in the region for all of Q4 would win a trip for two to the Kentucky Derby. The famous Churchill Downs racetrack is a client of Toshiba’s, and so the company has a couple of clubhouse level boxes right next to the track. Luckily I came out on top amongst the managers in the region! Judy and I flew down to Louisville for a few days to enjoy the sights, sounds, and once-in-a-lifetime experience of the “Most Exciting Two Minutes in Sports.”

Welcome gifts in our hotel room including Kentucky Derby swag, Woodford Reserve, wine, and some snacks

After flying through Charolette on a quick layover we landed in Louisville. The first night was to ourselves so we headed to the hotel to check in before going to dinner. Hotels are crazy booked during this time of year, so even our room at the modest Country Inn & Suites was over $600/night! Good thing this was an all expenses paid trip! Once we made it up to the room we were surprised to find some welcome gifts waiting for us.

It’s traditional to wear pink on Kentucky Oaks day in support of cancer awareness

After a night’s rest we were up bright and early to get ready in our derby attire. The two day event is divided into the Kentucky Oaks and the Kentucky Derby. The first day, the Oaks, is an opportunity for female horses to race. It is traditional to wear pink to the Oaks for breast cancer awareness. Judy put on a pink dress with her pink derby hat, while I decided to go with a pink dress shirt, tie, and pocket square. It took us several attempts to find a store in Minneapolis that had a selection of derby hates, but I think we were both happy with our final selections.

Our party was able to valet park which was great, as the crowds of cars were already starting to cause backlogs on the surface streets heading into the parking lots. Our seats were located on the 1st floor clubhouse level, only about 100 feet from the finish line (which can be seen in the background above). We were so close that we could feel the ground shake as the horses raced by!

Alcohol and horse racing. A winning combination at Churchill Downs

No shame here. Everyone drinks all day at the derby! For Kentucky Oaks the featured beverage is pink to match the color theme for the day. All drinks are served in a souvenir glass, which is cool until you realize that makes them $13 a pop! Again, good thing we weren’t paying for this trip! After a few races (and a few drinks) our group was given a tour of Churchill Downs. We got to visit a variety of areas including the paddock and Millionaire’s Row.

The famous Twin Spires of Churchill Downs, as seen from inside the paddock.
Very few people get to go into the paddock. We ran into a celebrity!

After a long day at the Kentucky Oaks we went to dinner at a local steakhouse. Once back at the hotel we were beat so hit the hay to rest up for the main event. The Kentucky Derby is like the Oaks, just 10x crazier. Thousands and thousands of people from all around the world attend to watch the races. It’s truly a once-in-a-lifetime experience. I even managed to place my first bet on a horse race ever! I bet on the actual Kentucky Derby race. My box trifecta hit and I won a little cash. Currently still batting 1.000 when it comes to betting on horses.

The Kentucky Derby… the only time I’d ever dress like this

Neither of us are really all that in to horse racing. In fact, before this I’ve never watched a race. But, by my guess, if you’re going to only ever go to one day at the tracks, it might as well be the Kentucky Derby!