(The official trophy for the 150th Kentucky Derby / Photo by Coady Media)

(Kentucky Derby 150 bottle of Woodford Reserve)

Editor’s Note:

Dan Liebman is one of the finest historians, writers and editors in the history of Thoroughbred racing. He wrote for “The Daily Racing Form,” and was the custodian, guardian and resident expert of the Dosage Index for many years. He was the Editor-In-Chief of “The Blood-Horse” magazine, one of the finest publications to ever cover the comings and goings of the industry.

More importantly that all those credentials though, Dan Liebman is one fine person, with class and integrity that drips from his fiber as deep and wide as the words from his finger tips.

Dan was the first partner I ever had in owning a race horse. That experience didn’t turn out great — economically. But it turned out great, because it helped deepen our relationship as friends.

Here’s Dan’s thoughts going into the 150th Kentucky Derby, and his personal thoughts of the last 50, which have left a great impression on a great man.

Dan Liebman: 

This past Saturday night, I was at Woodford Reserve Distillery for a ticketed signing event.

Woodford Reserve, located between Frankfort and Versailles, Ky., is the official bourbon of the Kentucky Derby and each year it produces a unique, collectible Derby bottle, adorned with beautiful artwork.

While always a special release, this year’s is especially so, because on this first Saturday in May they will contest the Run for the Roses for the 150th time.

This makes two years in a row marking an important anniversary, last year’s bottle featuring Secretariat, who had won the Derby on his way to Triple Crown glory 50 years prior.

Those in attendance Saturday night were fortunate enough to have their bottles signed by former Woodford master distiller Chris Mason, current master distiller Elizabeth McCall, and Kentucky artist Wylie Caudill.

Having been in attendance at Derby 99 (Secretariat) and Derby 100 (Cannonade), mingling at Woodford Reserve gave time to pause and think about the past 50 runnings of the country’s most beloved race by fans and coveted race by horsemen.

It goes without saying that each Derby is unique for many reasons, among them that the horses are being asked to navigate 10 furlongs for the first time in their career, that we always wonder about those not in the starting gate, and that the winner always seems to get “the dream trip.”

As a person who enjoys handicapping, the Derby is always a fascinating, but difficult, race to dissect. The distance, field size, huge on-track crowd, enormous amount of information … all come into play.

I’ve chosen many Derby winners, but my best overall job of handicapping the race came in 1990. After watching Unbridled in the Florida Derby and Blue Grass Stakes, I was confident he would win the Derby.

My pre-race column not only selected Unbridled to win but nailed the trifecta cold, with Summer Squall second and Pleasant Tap third.

In fact, because Churchill Downs did not offer the trifecta on Derby day in 1990, I dispatched a friend to River Downs to play the gimmick for us.

When I hit a huge ticket early on the 1990 Derby day card, I parlayed it on Unbridled.

I will never forget the trifecta numbers (7-11-8) and my framed photo of Unbridled signed by his trainer, Carl Nafzger, and the whip autographed by his jockey, Craig Perret, are prized possessions in my racing memorabilia collection.

My late friend Dr. Lenny Ludwig, who was married to my cousin, drove his family from New York to bet Pleasant Colony after having watched him win the Wood Memorial in 1981. I jumped on that bandwagon.

Having helped trainer Lynn Whiting obtain speed figures on Lil E. Tee so his owner, Cal Partee, could purchase him privately, I watched him win the race in 1992, my win tickets securely in my pocket.

I was at Fair Grounds the day Orb won the Florida Derby, watching on a small simulcast television. I knew then he was my 2013 Derby horse.

I loved Derby winners Silver Charm in 1997, Barbara in 2006 and Justify in 2018.

I had more than my share of Derby losers as well: I was convinced Bet Twice would win in 1987 (Alysheba won); thought Easy Goer was a cinch in 1989 (Sunday Silence); and knew Unbridled’s son, Empire Maker, would wear the roses in 2003 (Funny Cide).

Sipping Woodford Reserve while eating a country ham and biscuit, I also thought about one thing I know for certain after years of writing about racing and breeding — winning the Kentucky Derby secures a horse in racing history and lore, but it does not make the horse a good sire.

Granted Derby winners are certainly given a shot in the breeding shed. But peruse the list of the past 50 Derby winners and one will clearly see there are far more failures than successes in the stallion department.

But after all, the Derby is run to see who is the best 3-year-old on the first Saturday in May. It’s up to the stallion stations to “guess” who will make it as a sire.

It is tough enough to pick the Derby winner. What fun would it be if it were easy to predict which stallions will make it and which will not?

Consider this, the top five stallions in 2023 by progeny earnings were Into Mischief, Curlin, Gun Runner, Uncle Mo, and Quality Road.

Into Mischief missed the Derby due to an injury (but has sired two Derby winners (Authentic and Mandaloun), Curlin ran third in the Derby, Gun Runner ran third in the Derby, Uncle Mo missed the Derby because of illness, and Quality Road missed the Derby because of soreness caused by a quarter crack.

It should be noted that number six on the sire list last year was American Pharaoh, who won the Derby (and Triple Crown) in 2015. Derby winner Street Sense ranked 16th, Derby winner Justify 19th.

In 29th … More than Ready, another horse I was just sure would win the Derby (in 2000). He finished fourth.

The Kentucky Derby has so many interesting aspects to it. Its gives one so much to think about … perhaps while sipping a glass of bourbon.

In less than two weeks, another chapter will be written.

Riders up … and bottoms up.