If Big Brown wins the Triple Crown, the “sport of kings” will momentarily become the “sport of knaves.” The colt’s trainer is a boorish loudmouth who has a long rap sheet for illegally medicating horses. One of the partners in International Equine Acquistitions Holdings, which owns Big Brown, has a shady reputation from his days as a Wall Street wheeler-dealer in the 1990s.

In other words, Big Brown’s story isn’t likely to be made into a warm-and-fuzzy HBO movie anytime soon. Yet racing is so desperate for a Triple Crown winner that the sport will take one any way it can get it, even if the members of the racing establishment have to hold their noses as the Belmont Stakes trophy is presented.

Here’s what Andrew Beyer wrote of IEAH – it doesn’t have quite the ring of Calumet Farm, does it? – in a recent edition of The Daily Racing Form:

“When the company entered the sport in 2003, dealing mostly with cheaper stock, its trainer was Greg Martin, who had a knack for improving horses dramatically and inexplicably. One such horse, A One Rocket, became the focus of a federal investigation after he won a race for IEAH Stables.
“The trainer was found to have given A One Rocket a prohibited procedure known as a ‘milkshake.’ After Martin pleaded guilty to criminal charges and was drummed out of the sport, IEAH hired trained Rick Dutrow, who has a lengthy record of medication violations and a reputation (as did Martin) for being able to transform horses almost miraculously.

“When (Michael) Iavarone was asked about the rap sheets of his trainers, he observed that plenty of other respected stables have employed trainers, such as Steve Asmussen and Todd Pletcher, who have been suspended for medication violations.. ‘Our hope,’ he said, ‘is that racing is on the straight and narrow.’”

Iavarone and Richard Schiavo are the partners in IEAH. Their goal is to put together a syndicate of 100 partners each investing $100 million in a portfolio of race horses. Modeled after a hedge-fund, IEAH will take a management fee of two per cent per horse, plus 20 percent of net profits.

Who is Iavarone?

“I’m just a regular Long Island guy,” he told Newsday. “I’m a numbers guy.”

Well, not exactly.

In October, 1999, Iavarone was fined $7,500, censured, and suspended from the securities industry for 10 business days for association with A.R. Baron & Co., a New York firm that was the subject of a criminal and civil investigation.
Documents show that Iavarone was a general securities representative at A.R. Baron from July, 1993, until it collapsed in July, 1996. The following year, the firm was prosecuted by the Manhattan district attorney on charges of cheating thousands of investors out of $75 million. More than a dozen A.R. Baron officials either pleaded guilty or were convicted of wrongdoing.

According to records, Iavarone was accused of executing “unauthorized transactions which exceeded $22,000 in the accounts of public customers” in July and December, 1995, without his customers’ knowledge or consent. He did not admit guilt in the case.

About that same year, Iavarone said he ended his association with a now-defunct investment firm, Joseph Dillon & Co., which was censured in September, 2002, and fined $35,000. The firm’s chief executive was banned for two months by securities industry regulators for improper telemarketing methods. Iavarone told Newsday he had little involvement with Joseph Dillon, where he was a registered stockbroker, and had no knowledge of any wrongdoing.

At least Dutrow is more forthcoming about his problems. He has admitted to personally abusing drugs and alcohol. He also has admitted that he sometimes broke racing’s medication rules in search of an edge. “I’m a horseman,” he says, with a shrug, as if that explains it all.

And a damned lucky one, at that.

Bred by Dr. Gary B. Knapp’s Monticule Farms near Lexington, Big Brown is a son of Boundary, who stood for years at Claiborne Farm, out of the Nureyev mare, Mien. He was foaled on April 10, 2005, and purchased by Paul Pompa Jr. for $190,000 at Keeneland’s 2-year-olds in training sale in April, 2007.

Pompa named him Big Brown in honor of UPS, the international mail delivery service that has a major hub in Louisville, and turned him over to trainer Patrick Reynolds. The colt made his debut on Sept. 3, 2007, and rolled to an 11 ¼-length victory at Saratoga. After that race, Pompa sold 75 per cent of him to IEAH, which turned him over to Dutrow.

Ordinarily Dutrow doesn’t get that kind of potential dropped into his lap. Born on Aug. 5, 1959, Dutrow grew up on the race track. His father, the late Richard Dutrow, was a fixture on the Maryland and New York circuits. Both Rick and his brother Tony began working for their dad as children. At 16, Rick dropped out of school to become his dad’s assistant.

When his dad decided to move the stable to Maryland fulltime in the late 1990s – his health was failing and he wanted to be closer to home – Rick went out on his own. He was not exactly an instant success. In fact, he quickly was reduced to a one-horse stable and had to live in his tack room at Aqueduct.

To his credit, Dutrow persevered until he finally hooked up with Sanford Goldfarb, a New York commodities trader. He got his first stakes victory with Goldfarb’s Stalwart Member in 2000. Since 2001, Dutrow has been the leading trainer at eight meets in New York, and his main client, Goldfarb, led all New York owners in victories from 2001-’03.

Nevertheless, Dutrow’s success was tempered by his suspensions for medication violations. Horses improved dramatically after coming under his influence, and apparent it wasn’t entirely due to magic or his remarkable horsemanship.

Throughout the spring, Dutrow has alienated, entertained, amused and/or outraged – take your pick – the media and the public with Big Brown boasts. He predicted he would win the Kentucky Derby easily and selected the No. 20 post on the far outside – he had other choices – as if to prove that his colt could get all the worst of it and still prevail.
Which, of course, is exactly how it turned out.

Getting a perfect ride from jockey Kent Desormeaux, Big Brown stayed in stalking position until the top of the stretch, when he burst out of the pack to gallop all alone to the finish line. Two weeks later, he won the Preakness even easier, Desormeaux wrapping up on him the last eighth of a mile and hand-riding him to the finish.
Now Dutrow, who likes to call folks “babe,” has said that it’s a “foregone conclusion” that Big Brown will become racing’s 12th Triple Crown winner and first since Affirmed in 1978, and never mind that slight quarter crack in his left front hoof or the presence of Casino Drive, a new shooter who was bred in Kentucky but purchased and shipped to Japan by business mogul Hidetoshi Tamamoto.

After winning his February debut in Japan, Casino Drive was shipped back to the U.S., where he romped by 5 ¾ lengths in the Peter Pan Stakes at Belmont. His dam, Better than Honour, has produced the last two Belmont winners, the colt Jazil in 2006 and the filly Rags to Riches last year.

No big deal, Dutrow said in a May 28 teleconference.

“The Japanese horse has so much to prove,” Dutrow said. “I don’t know if he’s on the top of his game training (at Belmont). I would not depend on this horse for second (place).”

Later in the teleconference, Yamamoto’s racing manager Nobutaka Tada was asked if Dutrow’s comments offended him. “No, not at all. I enjoy listening to his comments. It sounds like he knows our horse more than us.”

He was probably just being polite, a foreign concept to Dutrow. During the same teleconference, he savaged the connections of Smarty Jones for blowing the 2004 Triple Crown. He accused the colt’s jockey, Stewart Elliott, of taking too much out of him in the Preakness, and said trainer John Servis made a mistake by working him on a sloppy track at Philadelphia Park the week before the Belmont.

While the media appreciates Dutrow’s candor – it’s great fodder for columns and sound bites – some also are ripping him for being arrogant and insensitive. In fact, the radio talk shows are humming with callers who say they’ll pull against Big Brown because they are offended by Dutrow.

Your thoughts on that, babe?

“There are people out there that think the wrong way of me, and that’s fine,” Dutrow said. “They don’t know me and just see what they are reading. Some of it is true and some of it just doesn’t add up. But I don’t really care. My job is getting the horse right and that is taking up all my time.”

The sport of kings is gearing up for a coronation. Big Brown does, in fact, look invincible. But the gods of racing often don’t smile kindly on knaves. It will be fascinating to see what sort of mood they’re in on Saturday afternoon at Belmont Park.