On the first Saturday in May, twenty horses will run the longest and most crowded race of their young lives. The Kentucky Derby, while not the richest race in the country, is the most recognized among the general public and so coveted by owners and trainers that the twenty starting gates have had no problem filling up in recent years, even though there are always a handful of horses that seemingly have no shot to win. The race is only open to three year-olds, so some will run despite not being in peak condition, because a horse doesn’t get a second chance at the derby. I can’t blame anyone with an eligible horse who wants to go to Louisville and give it a shot, I would do the same. Why not see if some magic happens? In 2009, Mine that Bird was fifty to one, had not won a race all year, and was dead last after the start, but he squeaked along the rail to pass the whole field and win it all. It was the last race he ever won and his career was otherwise ordinary, but I will never forget that horse and neither will the people that brought him to Kentucky.

I remember that race vividly because I had forty bucks to win on the horse that ran second, Pioneerof the Nile, who took the lead at the head of the home stretch and looked like a winner until that bolt of lightning came streaking up the rail to steal my money. The likely favorite in this year’s running is out for some family redemption. American Pharoah is expected to be about a two to one favorite in the Kentucky Derby. He is the son of Pioneerof the Nile and the grandson of Empire Maker, both runners up in the run for the roses. American Pharoah’s great granddad, Unbridled, won the derby in 1990. There’s nothing wrong with that pedigree, but perhaps what’s more impressive is his resume. After finishing fifth in his first race last August, American Pharoah won his last four races, all in stakes company, and his best win was his last race when he won the Arkansas Derby by eight lengths. Anything can happen in the Kentucky Derby, but if American Pharoah gets a good post position and breaks clean, he should have a good shot to win it all or at least get in the money.

The draw for post positions happens Wednesday, and while everyone will have different ideal starting positions based on their horse’s running style, no one will want to start from the one-hole. With twenty horses lined up at the start and about a half a mile to the first turn, there will be a wall of horses coming from the outside positions towards the rail. And a horse that runs straight out from the first post position run into the rail, so the horse that draws the one-hole has to move at least one path to the right while the others are moving multiple paths to the left. With all the traffic and jostling for position, the race can be lost in the first few hundred yards. In 2010, Lookin at Lucky looked like the best horse and was made a three to one favorite on the morning line, but he drew post position one and by the start of the race his odds doubled to six to one. Soon after the start he was checked hard into the rail twice and was shuffled towards the back of the pack. With too much trouble and too many horses to pass he wound up finishing sixth. He would come back in the Preakness to beat the derby winner, Super Saver, and was the best three year-old that year, but a bad post draw ruined his chance in Kentucky.

With a large field and a ton of money being bet on the race, the Kentucky Derby offers some unique wagering opportunities. Big money and big events attract the action junkies like me, and we bring our crackpot theories on how to bet the race. I’ve learned a few things from my past derby donations that might help you if you are new to betting the ponies. First, if you really like one horse in the derby, don’t just bet him to win, also throw down a bet to show. Most races I wouldn’t bother with a show bet because the payouts are usually weak, but with so many horses in the derby, the show payouts are always decent and often not much less than the place payouts. In 2012, a two dollar place bet on the favorite, Bodemeister, who ran second, paid out $6.20 and a two dollar show bet paid $5.60. For me, that difference is small enough to make the risk/reward on the show bet a much better value than a wager to place. Another betting strategy that has been a winner lately is to play exacta boxes with the favorite and every other horse in the race. With twenty horses starting, it would cost $38 to make all possible one dollar exacta combinations involving the favorite. If the favorite finishes first or second, the bet pays out, and if the other horse in the top two is a longer shot, it pays out well. In 2012, this bet hit and paid out $153. In 2013, it hit and paid out $490. Last year it hit as well and paid $170. I like this bet, not just because of its recent history, but the theory behind it has a certain yin/yang quality. On one hand, you accept the wisdom of the betting public and include the horse with the most money bet on it in every wager. But on the other hand, you acknowledge the unpredictable nature of this race and include all of the long shots because anything can happen. If the favorite doesn’t do it for you but another horse is calling your name, I’d try the same bet with your pick instead of the favorite. If I had done this the year Mine that Bird won, I would’ve turned $38 into $1,037. Learn from my mistakes, don’t let a horse you like hit the board and not get paid.

So if you don’t want to bet on the favorite, American Pharoah, what other horses are there to check out? The likely second choice might have the best record of any horse in the race. Saddled by multiple Kentucky Derby winning trainer Bob Baffert, who also trains the favorite, Dortmund is the undefeated son of Big Brown, one of the most impressive derby winners in recent history. Dortmund won the Santa Anita Derby by over four lengths and also has a win at Churchill Downs where the Kentucky Derby will be held. Most years he would be the favorite but this group is top heavy and a few others could make the same claim. One of them is International Star, son of another derby winner Fusaichi Pegasus. International Star won his last three races, including the Louisiana Derby, and has accumulated the most qualifying points of any derby contender, but he has not blown those fields away and the quality of his competition is suspect. Another top contender, Carpe Diem, is expected to be the third betting choice, which will be the first race he has not been favored in. He has four wins and one second in five starts and has won his last two races by open lengths. His trainer, Todd Pletcher, is one of the most successful trainers in America and has won the derby before. This will likely be the highest odds you will ever be able to bet Carpe Diem so if you like him, pull the trigger, but I’m not so sure.

For me, the top two choices will be tough to get past if they get a good post draw, but the most intriguing horse at longer odds is the foreign invader, Mubtaahij. With a trainer from South Africa and coming off an eight length win in the United Arab Emirates Derby, Mubtaahij is a horse that can break the derby curse on foreigners. Not many horses make the overseas trip to run in the derby and the ones that do usually are not much of a factor. Other winners of the UAE Derby have failed to hit the board in the past but that was when the race was run on a synthetic surface. This year the race is back on dirt, the same surface as the Kentucky Derby, and Mubtaahij won it in such a convincing fashion that I would not feel comfortable with any large derby bets that exclude him. To be sure, he has an uphill battle. International travel can be tough on anyone and his usual feed contains an ingredient not allowed by the FDA so his routine and his meals have been disrupted leading up to the race. But this horse looks to be improving and if he can handle the stress of traveling, he just might handle this field.

So I have some overall impressions heading into the week before the Kentucky Derby but I will not commit to anything until a few days before the race. I need some more time to geek out on pedigrees, past performances and post positions. After the post draw on Wednesday I will put together some bets and make them known here before the race. That way after the race we can all laugh at what an idiot I am and I can contrast my impressions of various horses before and after the race. Win or lose on my derby bets there will still be a level of excitement after the race because as long as the winner doesn’t collapse after the finish line, it’s on to Baltimore and the Preakness for another shot at the Triple Crown and a chance to recoup my losses.