In the 1870’s, a young man named George Elsworth Smith became fascinated by broadcasts of horse races that were played in the pool halls where he hung out. He spent a year writing down horse names, positions, winning times and any other information he could glean from the broadcasts. After a year of listening, taking notes and studying the information he had stockpiled, he placed his first bet on a horse named Gabriel at 5-1 running at Coney Island in 1879. Gabriel won and George cashed out a cool $38, the easy money got him to quit his job and focus on betting horse races. By 1885, despite never even seeing a horse race live, he had won over $100,000.

When Pittsburgh Phil, as George came to be known, finally attended his first live race, it was the Kentucky Derby. And as he didn’t see an angle worth playing, he didn’t wager a dime. 132 years later, the race lives on. Pittsburgh Phil’s edge is gone, we now have more information than we can possibly process constantly at our fingertips. But with so much noise to filter through, I have a feeling someone with a mind like that would still figure out a way to find a winning strategy.

I love the story of Pittsburgh Phil because beyond a love of horse racing I cannot relate to him one bit. He was as disciplined as they come and I lack discipline. I start betting first then figure things out as I go, and I could never watch a horse race, be in an area where I can bet on it, and not place a wager. Betting a little bit less on a race is my version of sitting one out. I like to have a strong opinion when I make a wager, but if given the opportunity to wager on something I have no opinion on, or observe the outcome with no financial interest, I’m making a bet, at least just a little something to make things interesting.

If you’ve read anything else about this year’s Kentucky Derby you’ve probably heard that it is a wide open race. It’s true that this is the first Kentucky Derby in four years without a clear cut favorite. I’ve seen lines that have Classic Empire as the favorite and I’ve seen lines that put him just behind Always Dreaming. And two other horses, McCraken and Irish War Cry, could reasonably vie for favoritism. In the past three years, there was a single standout horse in the derby, this year it’s hard to argue that any one horse is demonstrably better than the other top choices. I will do my best to make such an argument later, because for me one horse looks much the best. But by the morning line, this is as wide open a derby as we have seen recently.

The morning line is simply a guess at what each horse’s final odds will be after all the bets are made. It is not an indication of what the line-maker thinks the horse’s chances actually are. The fact that the aforementioned 4 horses are between 4-1 and 6-1 on the morning line tells me that even experienced horsemen aren’t really sure who will be the favorite at post time. Classic Empire was the champion two year old, but his three year old campaign has had some setbacks. Always Dreaming only ran twice as a two year old and never won, but he has been perfect as a three year old and his last win was the best of the season in my opinion. I wouldn’t be surprised if bettors flock to the horse with the best current form and make Always Dreaming the favorite.

Classic Empire won the biggest race of the year for two year olds last November. That stamped him as the early favorite for the Kentucky Derby. But in the first race of his three year old campaign, he finished a disappointing 3rd behind Irish War Cry and Gunnevera. Not a big deal, horses don’t always run their best, especially after a layoff. But after that race, Classic Empire refused to work out. This doesn’t happen often but when it does I love it. It makes the horse more relatable to me because sometimes I blow off my work as well. Despite the best laid plans of the owner and trainer, at any time a horse can just say, “up yours, I ain’t running today.” I like the headstrong attitude, but I shy away from betting horses that get finicky like that.

Classic Empire got his mind back to training just in time to win the Arkansas Derby and qualify for the Kentucky Derby. After that win, many feel this champion horse is back on track. With the best resume of the field, he is a deserving favorite. But for me, his win in the Arkansas Derby was by no means a statement race. Three other horses were within 2 lengths of Classic Empire at the finish line, including fellow Kentucky Derby entry Sonneteer, who has never won a race in his career.

The workout issues, the lack of a three year old resume and the fact that his best race this year was only 2 lengths better than a maiden are enough concerns to keep Classic Empire out of most of my bets. I won’t be shocked if he hits the board or even wins, but in a race like the Kentucky Derby, I can’t take a price that low on a horse that hasn’t wowed me once this year.

McCraken won his first 4 races and was favored in his last, where he finished 3rd. His last race was nothing special, but he wasn’t embarrassed. The best thing going for him is that 3 of his 4 wins came at Churchill Downs, the track that hosts the Kentucky Derby. Horse players like to bet horses at the courses where they win more often. I buy into this angle sometimes, but in this case I think McCraken was just facing weaker company in his wins.

Irish War Cry is an intriguing horse to me. He has won 4 of 5 races in his career. The lone loss was by 21 lengths to horses he has beaten before. He came back from that loss with a solid win in the Wood Memorial. If he didn’t have the one loss on his resume, he would likely be the favorite, he still may be. His last race has the highest Beyer speed rating of any horse’s last race in the field, and he is the only horse in the field to record multiple triple digit speed figures. He will be on my tickets. I think he has a good chance to win. But he is not my first choice.

Heading into the final round of prep races, I figured there was little chance I’d be betting the favorite in the Kentucky Derby this year. It worked for me the past three years, but favorites lose more than they win and no horse stood out enough to me to bet at low odds. But then I watched Always Dreaming dominate in the Florida Derby and now I’m a chalk eating fool once again, lining up with the ignorant masses to put my money down on the obvious choice.

No race or runner had made much of an impression on me this prep season until the Florida Derby. Always Dreaming finally showed me something special as he turned for home. Velasquez confidently rode the horse just off the lead. Before the turn for home he took a few peeks behind him to make sure no horse was closing fast. He knew he had the leader measured, he saw the best of the closers were too far off, then he shook the reins and Always Dreaming quickly opened up a multiple length lead. His style reminds me of previous derby winner California Chrome. And he drew post position 5, the same spot Chrome had for his derby win. And his last workout at Churchill Downs was the fastest of the day at that distance. He’s my horse and there isn’t a close second. That doesn’t mean he will win, I’m wrong more than I’m right with horse racing, but it’s nice to have a horse I believe in instead of throwing money at this race just because it’s the derby.

I love Always Dreaming’s style of racing. Deep closers come up just short way to often. They break your heart and drain your wallet because you want to believe that next time they will start their run earlier or have more ground or find less traffic and be able to get the job done. Speedballs look good for a while, but when the real running starts they are usually too tired to finish. Stalkers with a closing kick don’t find as much trouble as the closers and don’t get as tired as the need-the-lead type horses. Tactical speed is important, and Always Dreaming has it.

Always Dreaming has won every race this year by at least 4 lengths. In his last race, the Florida Derby, he ran the last 3/16 of a mile faster than any horse in the race despite running towards the front early. The Kentucky Derby at a mile and quarter is the longest race of these horses’ lives. How strong they finish in races at a mile and an eighth is seen as a good indication to how they will handle the extra distance. Always Dreaming’s strong finish last race on top of his excellent resume easily make him my favorite. Throw in a jockey and trainer that both have Kentucky Derby wins on their resume and I’m not sure how bettors won’t make him their favorite as well.

The horses with double digit odds that I like are Practical Joke and Gunnevera. Practical Joke has never finished worse than 3rd, is lightly raced as a three year old and may be improving. His mid-pack running style with a late kick could work well in this race if the oversized field produces a hot pace up front. Gunnevera could also benefit from a hot pace. He has the best resume of the deep closers. He does his best running late, and since this race is the longest of these horses’ careers, there should be plenty of tired horses to pass. Will he pass them all? I don’t think so, but it’s possible. My disdain for closers that I wrote about earlier is likely why I see Gunnevera running late to hit the board, but not pass the winner. If I believed in closers, he might be my play, especially because he’s got a great story.

His trainer, Antonia Sano, is from Venezuela. He trained horses there before the current economic collapse. As poverty and crime spread he was kidnapped twice, the last time for over 30 days before family and friends could get the ransom money to free him. He came to America with no horses, just experience and a willingness to work. He found some owners that believed in him, claimed a few horses and started building a stable. He found Gunnevera at a yearling sale and purchased the horse for $16,000. Gunnevera has already won over a million dollars in his career and Sano is training a horse that is running in the Kentucky Derby. That’s living the American Dream. What’s not to like?

As for how I will bet the race, I’m going to do what I always do in the derby and bet a $1 exacta box with my favorite horse, Always Dreaming, and the field. I will bet an extra buck on the exacta box with him and the other favorites, or horses I like, such as Gunnevera, Classic Empire, McCraken, Irish War Cry and Practical Joke. That puts me at $48, I’ll put $20 to win on Always Dreaming and play a $1 trifecta and superfecta with Always Dreaming on top and Gunnevera, Irish Way Cry and Classic Empire boxed underneath. That’s $80 total.

I’ve turned a profit on my posted bets for Tilting Ground two years running and I’d like to make it three. This is about more than money to me, although, to be fair, it’s mostly about money. I’ll likely make a few more ill-advised wagers just before post time and if one of those hits big while the bets I gave you suckers flop, I will laugh all the way to the bank and not feel bad for anyone that lost money betting with me. It’s your fault for betting. That’s why they call it gambling.

Enjoy the race. And remember, don’t bet more that you can afford to lose…unless you win.