John Messara, It's A Dundeel and The Championship race that is worth $4 million

When It's A Dundeel swept past the winning post to claim the $4 million Queen Elizabeth Stakes – the richest race ever run on a Sydney track – the owners, who included John Messara and broadcaster Alan Jones, were jubilant.

But there were other industry figures who were deeply worried about how it would look: Mr Messara, the chairman of the racing industry's governing body, had not disclosed that he had obtained an option to buy race favourite It's A Dundeel while presiding over the decision to increase the prize money for that race from $500,000 to $4 million.

Nicknamed "The Messiah" by wags in the racing industry, the 68-year-old Egyptian-born former stockbroker is a polarising figure in the thoroughbred world. He is charismatic, driven and feared.

His power has been buttressed by his friendships in Macquarie Street and also by his friendship with Alan Jones, who has used his radio program to champion both the racing industry and the ambitions of his friend.

The triumph of It's A Dundeel, which was immediately retired to Mr Messara's stud, was not the first time concerns about Mr Messara's potential conflicts of interest had been raised.

When the government appointed Mr Messara chairman of Racing NSW in December 2011, critics queried his suitability given his vested interest as a major breeder.

Decisions he makes as chairman of Racing NSW have the potential to advantage the breeding industry and he just happens to own the Arrowfield Stud in the Hunter Valley, the country's biggest Australian-owned breeding operation.

In the past, those caught expressing concerns about Mr Messara's potential conflicts of interest have been threatened with legal action by the prominent breeder.

"All that I said was if Messara gets the job – will he act in the best interests of racing or the best interests of John Messara?" said one well-known industry figure on the receiving end of a Messara legal threat several years ago.

During the course of Fairfax Media's investigation, Mr Messara sent legal letters to a raft of people accusing them of making false and defamatory statements about him.

Adam Kilgour, chairman of the NSW Trainers Association, said he was "astounded" to receive two legal letters accusing him of making defamatory statements about Mr Messara.

The letters also demanded Mr Kilgour provide details of other people who may have been defaming Mr Messara.

Mr Kilgour told Fairfax Media his role was to advocate the views of horse trainers, which often differed from Mr Messara's. "But last time I looked, it wasn't a criminal or civil offence to express an alternative point of view in Australia."

"John is always welcome to come to a trainers' association meeting to hear first-hand what trainers think of the industry he is responsible for," said Mr Kilgour.

Back in November 2013, as head of the state's racing industry, Mr Messara announced the launch of "The Championships".

The NSW government had kicked in $10 million to make two days of racing during Sydney's autumn carnival among the most lucrative in the world.

Then racing minister George Souris told Fairfax Media he wanted the feature race for Sydney's autumn carnival to be worth $5 million "to blow the Melbourne Cup out of the water".

Racing NSW decided the jewel in the crown of The Championships would be the 2000-metre Queen Elizabeth Stakes and that its prize money would skyrocket from $500,000 to $4 million.

Not everyone in the industry agreed with the choice.

"We thought it was ridiculous," said one racing executive involved with the discussions. "Any punter or breeder will say fine to double or treble it but not to make it $4 million."

The Australian Turf Club wanted the better-known Doncaster Mile to be the feature race but Mr Messara successfully argued that a 2000-metre weight-for-age race would appeal to international competitors.

In September 2013, two months before the unveiling of The Championships, Mr Messara negotiated an option to purchase a 30 per cent interest in It's a Dundeel after the horse's impressive win in the Underwood Stakes, bringing to an end Atlantic Jewel's nine-race winning streak.

The option was exercised in November and in December Arrowfield's syndicate took its ownership of the champion stayer to just under 75 per cent. The rumoured cost was $10 million.

Asked if he should have declared his interest in one of the top prospects for the race when the prize money was being discussed, Mr Messara said, "No, not at all."

"Conflict of interest is a state of mind, in my view," he said. "I know … it looks like a Machiavellian plot, but it wasn't."

"Anyone who understands racing knows that it is ridiculously speculative. There is no certainty. I didn't buy it and then say to myself, 'I will win that race'."

Mr Messara also said anyone could have bought the horse as it had been widely speculated in the industry that there was going to be a big injection of prize money into the 2014 autumn races.

"It's a Dundeel was going to be a contestant, but everyone in the world knew that," he said.

But whether It's A Dundeel won the race or not, the fact such a huge amount of money was put into a staying race over 2000 metres would encourage breeders to use stallions proven over that distance, say insiders.

This would not just help market It's A Dundeel in his second career, as his previous big wins included races at 2000 and 2400 metres, but also two horses Arrowfield had recently invested in: Kentucky Derby winner Animal Kingdom and another American horse, Gio Ponte, which had won at the highest level over 2100 metres.

Mr Messara's potential conflict of interest in owning the race favourite had already seen tensions boil over in the days leading up to the running of the Queen Elizabeth Stakes on April 19, 2014.

On Tuesday, April 15, It's a Dundeel drew barrier one, the closest to the rail. The following day racing stewards decided to move the rail another three metres because of the rain-affected track.

Lindsay Murphy, the Australian Turf Club's racecourse manager, was furious.

The rail had already been moved three metres and he argued that only in exceptional circumstances should the rail be moved again, especially after the barrier draw had been done and punters were betting on the race.

ATC boss Darren Pearce knew staff were upset about the second rail move but, after walking the heavy track with chief steward Ray Murrihy, he agreed with the steward's decision.

Mr Pearce rang Peter V'Landys, Mr Messara's right-hand man and the chief executive of Racing NSW. Mr Pearce relayed his staff's concerns that "everyone is going to say we did it for Messara" and that Mr V'Landys might need to address this potentially damaging perception.

"No, he wasn't passing on any concerns to me," said Mr V'Landys of the call. "He was being apologetic that someone would make such a reckless accusation."

The ATC's general manager, Matt Rudolph was one of those concerned about the perception that It's A Dundeel had been given an advantage.

"I feel sick to the stomach – we are going to look compromised," he told an associate.

Despite being advised by colleagues to let the matter go, he took the matter up with Mr Messara.

"There's already enough talk about your horse being the favourite for this race. It would be a very bad look if the rail is moved out further after the barrier draw," warned Mr Rudolph.

"I remember that scuttlebutt after the rail had been moved. I knew nothing about it, nor should I have known anything about it," said Mr Messara.

Mr Messara was not involved in the decision to move the rail and he told Mr Rudolph that.

Insiders say the relationship between Mr Rudolph and Mr Messara and Mr V'Landys was downhill from there. Mr Rudolph, who declined to comment for this story, is currently appealing a two-year disqualification by Racing NSW over an unrelated matter.

"He was meticulous about everything to do with this race," said another racing official about Mr Messara's request for a specific stall at Randwick on race day.

As a stallion, It's a Dundeel was known to be temperamental and Mr Messara wanted to make sure he was stabled in the quietest area away from any potential distractions.

As it turned out, the highly-strung horse suffered a minor injury just before the race. On hearing this, part-owner broadcaster Alan Jones bolted down from the Directors' Room to inspect him.

He need not have worried. It's A Dundeel, sporting Arrowfield's racing silks of gold and black diamonds, swept past the winning post to claim the world's richest 2000-metre turf race.

"We've been aiming for this all along," said jubilant trainer Murray Baker.

As race goers know only too well, racing is all about chance and luck and there was never any guarantee the horse would win.

But win he did. The Queen Elizabeth Stakes was his last race. It's A Dundeel, now known as Dundeel, was immediately retired to the lush pastures of Arrowfield.

His stud prospects were boosted by the massive increase in his winnings and he now generates around $3 million a year servicing mares.