Kentucky Derby, a race Godolphin is yet to conquer

Sheikh Mohammed bin Rashid's Godolphin operation has tried a new approach for this year's entry to North America's most famous race.

Godolphin has never finished better than sixth, back in 2000 with China Visit, in the Kentucky Derby at Churchill Downs. The Dubai operation has taken a different approach with this year's entry, AlphShow more

Back in 1945 when the world contained no colours and people lived entirely in black and white – go check the videos if you don't believe me – a great jockey dismounted an excellent horse and said a memorable thing to an inexperienced owner.

"That's the most expensive race you'll ever win," said Eddie Arcaro, finishing a Kentucky Derby win aboard Hoop Jr, the first horse Fred W Hooper ever bought.

"What?" Hooper said, as goes the oft-told story.

"You'll spend the rest of your life trying to win it again," said Arcaro.

One of the world's biggest puzzles will play for the 138th time on Saturday with the solving expected to lure the usual 150,000. The Kentucky Derby again will take the ample brains of shrewd businessmen and turn them into mush until it registers in their eyes as starry.

It's both the stuff of gooey dreams and much more of a lottery than most horse races, something to consider as the Godolphin Stable of Sheikh Mohammed bin Rashid, Vice President of the UAE and Ruler of Dubai, prepares to try for the sixth different year with an eighth different entry. As Sheikh Mohammed once told the author Jason Levin: "The Kentucky Derby is a more difficult race to win than I first believed."

Decisively favoured to win on his first try in 1992 with his co-ownership of Arazi - Arazi finished eighth - Sheikh Mohammed has his ninth entry, China Visit's sixth place in 2000 still the best yet.

His Godolphin stable has its eighth entry and first since 2009. That would be the moderate hope Alpha, provided Alpha makes it to the starting gate after a recent injury, with five weekend furlongs in New York hinting he will.

You might say the mighty Godolphin has "failed" at the Kentucky Derby, or you might say that with a few glaring exceptions in certain years, the verb "failed" ought to be left off the premises of anything so zany. This coveted thing has a heaving raft of goofball statistics.

The Hall of Fame trainer Bill Mott, who famously brought Cigar here in 1996 for the first Dubai World Cup, is a judicious deployer of horses yet has done no better than eighth in seven tries.

The future Hall of Fame trainer Steve Asmussen, who famously brought Curlin here in 2008 for a Dubai World Cup win, finished third with Curlin in 2007 among 10 failing non-failures.

The retired Pat Day won more races than any jockey ever at Churchill Downs, yet the Derby site, and his mounts across 22 consecutive years included favourites such as Demons Begone in 1987 and the much-trumpeted Easy Goer in 1989. He won once, in 1992, aboard Lil E Tee, profoundly forgotten as the gates opened.

The Hall of Fame trainer Nick Zito won on his second entry in 1991 and on his third in 1994, yet has entered 22 non-winning horses since, five in 2005 alone (including the favourite), and while it always seems it would be hard to follow five horses through one two-minute race, it is surely even harder when they run seventh, eighth, 10th, 14th and 15th. The sure-to-be-Hall of Fame trainer Todd Pletcher had 24 entries before he won in 2010 with an entry not the most favoured of the four that year.

Between 1985 and 1989, the Derby winner became the American Horse of the Year winner four times out of five. Between 1990 and now, it has happened once.

Even for horse racing, it's mass hotchpotch.

The horses, aged three, have not formed themselves yet. The entry total, usually 20, is excessive. And many hopefuls do not make the race, a fate that hit Godolphin with Street Cry's ankle injury two weeks before the post in 2001.

With all that and more, it is no wonder that even the most seasoned experts fiddle around with approaches. Godolphin typically kept entries in the UAE before flying over, with Express Tour in 2001 running zero American preparatory races as an example. Even back then, the Godolphin manager Simon Crisford told the Associated Press: "You've got to give it a number of years before making any hard and fast judgements."

As evidence of that 11 years on, Godolphin has veered to a fresh approach. Alpha has stayed in America, winning twice in 2012 and finishing a yeoman second by a neck after stout trouble in the Derby-preparatory Wood Memorial in New York.

As the estimable Jay Privman summarised in the Daily Racing Form: "Clobbered on the first turn, made nice run to get back in race, but couldn't go by Gemologist."

As of yesterday, the Daily Racing Form ranked Alpha eighth in its Kentucky Derby Top 20, with Gemologist fourth behind Bodemeister, Union Rags and Creative Cause. So for Godolphin, it is probably not, but maybe.

This probably-not-but-maybe race has bedazzled men for years, including even Fred Hooper, who won in 1945, aged 47, and whose amazing life warrants no pity, even though he never won the Derby again in three tries while having one favourite and one horse who led in the stretch.

He died in 2000, aged 102.

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& Chuck Culpepper