The 144th Kentucky Derby, to be run Saturday at Churchill Downs in Louisville, has many intriguing angles, none more so than whether Irish horse Mendelssohn can be the first from the Emerald Isle to win the “Run for the Roses.”

He does not lack the connections. His trainer Aidan O’Brien is perhaps the best trainer in the world; the owners, John Magner and Michael Tabor, have built a breeding empire in Coolmore, Ireland; and the jockey Ryan Moore is the best in Europe.

The word is that Tabor and Magner have had a real gamble on the horse during the week with British bookmakers, and given they are considered among the shrewdest men in the game, it seems they like their chances.

The horse himself is not to be dismissed either. He cost $3 million as a yearling. He won the Breeders Cup 2-year-old on turf before winning a major race in Dubai on dirt. He has been highly impressive, especially in his last race in Dubai.

Read more: The First Steps of 'The People's Horse'

Cool Dude Mendelssohn the "you lookin at me punk" look

Picture Courtesy of @KentuckyDerby

— AIDANOBRIENFANSITE (@aobrienfansite) April 7, 2018

His sire is Scat Daddy, who was a dirt champion, which makes it likely Mendelssohn will take to the surface at Churchill Downs, which has its own peculiarities.

Unlike previous O’Brien contenders who were brought over on a wing and a prayer, Mendelssohn is lurking with real intent.

Read more: A Kentucky Derby 2018 favorite horse is from Ireland

He is one of the most experienced runners in the field which means a lot in the Kentucky Derby. He is drawn well and has the speed to stay in touch with the leaders which is often not the case with European horses.

The X-factor in racing luck. With 20 horses in the race, the start and the race to the first bend are critical moments as horses seek position and bumping and collisions are likely as the outside horses seek to move in.  

Mendelssohn is listed the second favorite to Justify, the Bob Baffert horse, who everyone agrees is the most talented horse in the race but lacks critical 2-year-old experience.

Tales from the Crib: Mendelssohn ➡️

— Kentucky Derby (@KentuckyDerby) April 6, 2018

How critical is that factor? Well, no Kentucky Derby winner since 1882, when a horse called Apollo cantered in, has ever won the Derby without racing as a two-year-old. That's a very long jinx and it means you will be only getting 3/1 or thereabouts on the colt beating a 136-year-old streak.

No thanks.

That non-race as a two-year-old also rules out Magnum Moon who is a hot pick and won the Arkansas Derby very easily.

Todd Pletcher, who would rival O’Brien, has no fewer than four contenders in the race, with Vino Rosso and Audible his best two. Stable jockey John Velazquez picked Vino Rosso over Audible which is good enough for me.

The other contenders I like are Breeder’s Cup Juvenile winner Good Magic and Justify’s rival on the West Coast, Bolt D'Oro, a vastly experienced horse suited to the inevitable rough and tumble.

Read more: Outrage as horse raced to death on streets of Cork



— Meydan Racing (@DRC_Meydan) May 4, 2018

But it is Mendelssohn for me for a famous Irish victory with Justify, Bolt D’oro and Vino Rosso rounding out my top four.

Also keep an eye out for Dublin-born James Graham, riding an outsider Lone Sailor, who looks outclassed, however.

Who are you placing your money on? Let us know in the comments section, below.