Alas, the first Saturday in May is upon us once again and we all know what that means. The annual running of the Kentucky Derby and what affectionately is known to most as "The Run for the Roses". But for life-long horse bettors it might as well be named "The Run for the MOSES". Because the challenge of picking a winner is equal to sprinting through the desert without water or maybe parting the Red Sea.

The one common thread for all handicappers is it's the one race they all want to win the most,  more for remembering and bragging than any money they won. The bread comes and goes but the memory you selected the winner for a specific year stays in your mind for a lifetime. Yeah..it's nice to isolate a Breeders Cup winner or cash a fat exacta but there's nothing like spending an entire week handicapping and agonizing over the Derby. And then changing your mind who to bet with five minutes to post.

Here's several reasons why "the greatest two minutes in sports" can often be the worst for those who take wagering seriously. And how it is uniquely different than the thousands of races taking place in the U.S. throughout the year.

Location, location, location
Churchill Downs is a mammoth place that keeps getting bigger every year. It is built entirely to accommodate the average 5,000 people than show up for an average race day. But Kentucky Derby Day is far from average when about 155,000 or so form a small city there. Horses never see anything close to it and often get spooked out of their minds. Add in the marching bands, fireworks, crazy hats plus army of police security and many thoroughbreds would run for the Louisville Airport if they could. Saratoga is not the only graveyard of favorites. Many 9-5 shots have mysteriously run off the board in the Derby and all other races during the Derby Day card.

As a configuration Churchill Downs also has a very long stretch that has been lengthened in recent years. Many horses are coming off key races at prestigious Gulfstream Park in Florida, which has a much shorter stretch run. Some hit mid-stretch without much stamina left and ask themselves "what's going on here". Especially going the classic Derby distance of a mile and a quarter.

In the Long Run
Speaking of the mile and a quarter, the unique distance is likely the biggest factor that makes handicapping this race so impossible. For all of these horses it will be the first time they have faced this intimidating test and likely the last. Books are written on who has the classic pedigree to get the added distance based on mathematical formulas, indexing and various other scientific crap that sounds impressive. It usually isn't.

You can look good, sound good and wear all the right clothes but until you ask the girl to dance you'll never know. It would always help to know you've done it before or been there before. Last year was an exception with Triple Crown winner American Pharoah. AP's sire was Pioneer of the Nile, who was second in the Derby and won several races at classic distances. He got his speed from his mother, or dam who excelled in sprint races. But overall many horses in Derby fields by long-distance sires have flopped. Later in the year it's relevant but not this early in their young 3-year old development.

Expect lots of Traffic
If you're attending the Derby without an expensive reserved seat you might want to show up at 6AM to help avoid the 155,000 in the crowd. If you're a jockey among the crowded 20 starters you want to pray your horse gets away cleanly out of the starting gate as a first step.

Virtually all horse races run in the U.S. average between 6 to 8 starters per race. Some can have as little as 4 and some as many as 12 a maximum of 14. The Kentucky Derby is aimed and planned to have a crazy 20 starters based on a points earning system. It was at one time up to 24 and then narrowed down to a maximum 20 in the starting gate. Scratches are possible but usually unlikely until the day of the race for last-minute illness.

At post time a clock consuming process begins for the 20 starters loaded into an auxiliary starting gate that is never used for any other race. Once the race begins it causes a certain "cavalry-like" traffic nightmare for at least 5 to 6 horses victimized by bad luck. You can bet on that. A few will be instantly eliminated as the gate opens. More will be shut-off during the race, especially if it happens to be an off-track due to bad weather conditions. It is possibly to overcome a bad start but unlikely.

Some very forgettable horses have won the Kentucky Derby because they got lucky, got a clean trip and were in the right place at the right time. During the last ten years very ordinary horses like Orb, Animal Kingdom and 53-1 Giacomo can lay claim to that definition.

Who's a Mature Horse?
Just like humans, some horses mature faster than others. Think of a top 3-year old in the first week of May being equivalent to a top young basketball player. Unless it's LeBron James, it takes most players at least until they're 24 or 25 to peak. Horses grow and gain experience tremendously by September through November when they race in the Breeders Cup. By then they're physically more mature and more mentally prepared. They've been at several race tracks among huge crowds. Facing this mammoth challenge for the first time is really unpredictable.

For that reason, is often why those who finish the Derby fifth on down don't return for The Preakness in two short weeks and set their sights on big races during the Summer and Fall. Maybe they'll rest up for the Belmont Stakes, which is five weeks after the Derby is run. Often by the second week of June it's amazing how much valuable weight they put on and start to mature.

The Best Bet
Isolate other races at other race tracks on Saturday to wager the majority of your betting funds. Think of the Kentucky Derby like the Super Bowl and enjoy it for purely the unique spectacle it is. The most memorable horse race of the year and THE greatest two minutes in sports. Not that you're obligated to win more money.

My last big Derby winner was Funny Cide, way back in 2003. Nobody even remembers who that was. Maybe because he was a gelding with obviously no chance to have fun and bear expensive offspring in the breeding barn. I do remember betting against Barbaro in 2006 and Mine That Bird in 2009. I think they made movies about them. Oh well.

Glenn Greene covers the games from a betting angle every week exclusively at OSGA.com. For weekly betting insights, inlcuding previews and picks from Glenn, click here.