The Casual Bet: Guest Handicappers Analyze The 2024 Kentucky Derby

Featured in Illustration: Affirmed and jockey Steve Cauthen Winning the 1978 Kentucky Derby (Illustration Courtesy of Esmé Bleecker-Adams)

To pull back the curtain on the Paddy’s Picks process, I usually write the introductions to these articles at the end. The problem is that I’m currently in a car in the middle of Pennsylvania on the way to my sister’s graduation. So you’ll all have to forgive me if I’m a little succinct in setting the stage for this year’s Kentucky Derby. read more

Paddy’s Picks 2024 Kentucky Derby Analysis

A Kentucky Derby without Bob Baffert is like an oil tanker without a fireworks display. Plenty of things can still go wrong, but you’re feeling a lot safer onboard, aren’t you?

Instead of transferring his Derby hopefuls to his colleague, Tim Yakteen, this year, Baffert tried to get around his Churchill Downs ban through the Kentucky Court of Appeals. The court’s decision to enforce the racetrack’s restrictions is a clear win for those who consider Baffert’s doping history to be a stain on the sport. From a purely competitive point of view, however, it is unfortunate that superstar colt Muth, along with a few others in Baffert’s stable, are therefore ineligible to run. read more

Make Your Case: Guest Hancidappers Defend Every Horse in the 2024 Kentucky Derby

In the early 1600s, Catherine de Vivonne, marquise de Rambouillet, grew tired of the social scene in France and began hosting small events in her salon. In time, these events and others like it became highly fashionable, allowing intellectuals across various disciplines to exchange concepts and ideas on the basis of reason. Thus began the Age of Enlightenment. 

Nearly 200 years later, King Louis XVI was beheaded by guillotine in the Place de la Concorde. 22 years after that, the tyrant Napoleon Bonaparte was exiled for the second time and sent to die off the coast of Africa. read more

Handicapping Medley: Saturday, May 27, 2023

For those of you who don’t know me too well, you should know that I get distracted very easily. It’s hard for me to directly progress from one thought to another, and even as I write this paragraph, I’m tempted to stray. This cognitive wanderlust applies to horse racing as well, and I might have finally created an article that satisfies my curiosity.

Whenever I peruse entries for a certain day of racing across the country, I invariably find myself drawn to races at different tracks. Weekend cards are especially frustrating for me, as I can’t possibly analyze every event that entices me. But what if I tried? What if I took note of every race I liked and created a sort of handicapping medley? What if that was what I named the article? Woah! read more

Fillies, No Fellas: Looking Back At Guests’ 2023 Kentucky Oaks Picks

In a revival of last year’s segment of the same name, I asked nearly every woman who has ever appeared on Paddy’s Picks to provide a pick for the Kentucky Oaks. The primary motivation for originally making this article was the opportunity to use the phrase, “Fillies, No Fellas,” the origin of which I’ve forgotten, but it actually turned out well enough to try again.

Unlike last year’s piece, this article is being published after the Kentucky Oaks, giving me the opportunity to provide grades for every single pick. Yes, letter grades. There are two ways that readers can interpret this editorial choice. Assigning grades could allow me to write less while hopefully still providing a fun environment for contributors. It could also allow me to pass harsh judgment on people who don’t know what they’re doing. I refuse to elaborate further. read more

Race of the Day: 2023 Kentucky Derby Analysis

I woke up this morning and the sky was falling. Several of my guest handicappers had already heard the news and were frantically texting me. It’s taken a few hours, but I believe I’m finally ready to complete my Derby analysis once and for all.

Kentucky Derby favorite Forte’s withdrawal from the race this morning sent shockwaves throughout the racing community as everyone frantically tries to evaluate the race without him in it. It feels more wide open than ever and I’ve had to slowly come to a new understanding. read more

Why They’ll Win: Making a Case for Every Horse in the 2023 Kentucky Derby

We’ve all had that moment at the track where we look at a horse in the Daily Racing Form and get hooked. All the signs of a winner are there, and the warning bells that ring perpetually in handicappers’ ears become dulled by an attractive price on the tote board.

It’s surprisingly easy to grow enamored by stats on paper, especially when they’re inextricably tied to potentially profitable flesh and blood on the track. But when these feelings set in, some self-doubt may form as well. read more

The People’s Race: Kentucky Derby Guest Analysis

Everyone needs a pick for the Kentucky Derby. It’s mandatory in my opinion. Every year in May, 20 entrants run in the most chaotic event in North American horse racing; it’s an opportunity for the most experienced and most fun-loving to congregate for a relatively random chance at a massive payout. 

For the race that everyone should have a pick for, I asked — well, almost everyone, but I tried to focus on people that wouldn’t have picked a horse otherwise. Annoying people in the name of racing awareness is kind of my thing at this point. They never see it coming. Within this chaotic piece, prophecies, gut feelings, mispronunciations and sound logic await. I’ve made no attempt to organize any of it. Happy Derby Day! read more

Road to the Derby: Kentucky Derby Analysis

We’re at our last stop, aren’t we? After months of studying in an effort to understand the Kentucky Derby, 20 horses will now converge at Churchill Downs. I’ve made money on a few of them, lost more on others, but it has all led to this. Let’s see if I’ve learned anything.

By now, I’ve waxed poetic about the history, opined about current events in the racing world and given you a little about my personal life in this series along the way. Hell, I told my readers about an ill-fated karaoke experience, if that ever meant anything to you. But as the Derby approaches, this one should come down to the analysis. Let’s get to it. read more

Fillies, No Fellas: Kentucky Oaks Guest Analysis

Most years, the running of the Kentucky Oaks the day before the Kentucky Derby is little more than a stepping stone to the feature event of the weekend. After all, most fillies simply aren’t as fast as the colts, and the Oaks represents their initiation into all-female competition for the rest of their careers. 

But sometimes, the Kentucky Oaks represents the first step in one of the most interesting circumstances in racing: a filly proving herself and going on to face the boys. In this sense, it represents hope and doesn’t happen often. Rachel Alexandra did it in 2009, winning the Oaks before defeating Derby winner Mine That Bird in the Preakness. Swiss Skydiver did it in 2020, finishing second in the Oaks before defeating Derby winner Authentic. This year, four fillies seem qualified to take this rare step forward. This isn’t just your average year. read more