An old man once said to horse owner and broker Terry Henderson that when the moment came for his life to pass before his eyes, he would want to have plenty to watch. It has stuck with him.

Already on his highlights reel there is a Melbourne Cup win, also two hair's breadth second places, and a scheme for more, perhaps as soon as Tuesday. He has vital interests in four/five runners this year.

Henderson also has run his own successful business, completed the Marathon des Sables, a seven-day, 250-kilometre footrace in the Moroccan desert, hiked in Iceland and Patagonia, climbed fabled Mt Kilimanjaro, written a book on jogging around the world, and a novel fashioned around tennis in Peru, as yet unpublished. You could say that he knows about staying power.

He is far from finished. Horse people don't retire, he says, they die in the figurative stirrups. He expects to be one of them. This is despite that fact neither Sue, his wife of 46 years, nor his any of three children have an interest in thoroughbred racing, though he thinks he might have piqued the imagination of the oldest of his eight grandchildren, 10-year-old ???.

Playfully, he texted her the other day to ask if she could ride one of his Cup horses. "I sure can," she replied, "but the horse might finish the race without me!"

It is not that Henderson mixes business with pleasure; they are one and the same to him. As a syndicate manager, he cherishes the collective aspect of thoroughbred racing, which he says is unique to Australia. Win, lose or scratch, he expects to spend this week at "wall-to-wall parties" of owners, some merely of a fetlock, but all thrilled none the less.

In Europe and the US, where he spends half his life scouting and buying horses, Henderson says it is not nearly so communal. "They don't have any concept of sharing," he said. When he looks at a racebook, he knows why: there's the Queen, the Agha Khan, a sheikh or two, but none who need to take the hat around. It makes him feel poor, but only for a moment.

"I'm reasonably well off, but it's not because of horses, let me assure you," he said. "It's not that sort of business. It's for the passion of racing horses."

For Henderson, it began humbly enough. To describe his family circumstances, he settles on the word "dysfunctional". His father left when he was young, leaving his mother to do the raising. "But I got pretty much a free education from the Christian Brothers," he said.

Horses did not run in the family. He found them for himself, trotters at first, gallopers in his late teens. "I used to punt," he said, "but I was absolutely useless at it." No one deterred him. "Half the Christan Brothers are desperate punters anyway!" he said.

At 20, Henderson married 17-year-old Sue, and says he is as much in love with her now as then. He trained as a transport economist, founded his own logistics management company and pursued his interest in racing, though strictly from this side of the rails and stalls.

"Training's so hard," he said. "If you asked whether it is harder to run BHP or Peter Moody's stable, I'd say BHP was easier any day." Moody has to deal with the element of chance as the CEO of BHP never does, he said. And BHP's debtors pay their bills.

Henderson dabbled in trotters, owning in syndicate Chokin, which was twice New Zealand harness horse of the year. But at length, he concentrated on thoroughbreds, and in 1995 he and his syndicate won the Caulfield/Melbourne Cup double with Doriemus.

"I still had the management consultant practice, and what I still remember is that all of a sudden, instead of having to knock on doors and wait for clients to ask you in to tell them about your wares, they were ringing us. It was because of the Melbourne Cup. People always like to be associated with success. It wasn't that long after that I was approached to sell."

Two years later, Doriemus ran second in the Cup to Might and Power, which Henderson said was the just result on the day. "He'd fought off five challenges; we were the last," he said.

In 2008, when Bauer lost by a sliver to Viewed, the sentiment was different. "We thought we'd won," he said. "I usually judge the finish at Flemington by the horse's backside. From where we sat, Bauer's backside was clearly in front of the winner's. It was a shock. But you win $1 million for second, so who should feel sorry for you?"

By then, Henderson had sold his business and, swapping his vocation for his obsession, had gone into a racing partnership called OTI with former Test cricketer Simon O'Donnell. OTI scours the world for likely stayers to buy and syndicate, as business propositions, of course, but also in Henderson's mind to reinforce the integrity of the Melbourne Cup.

He thinks recent lobbying for a cap on internationals is dangerously misguided. "If you want an international race that's going to have the exposure and the respect that this race now has, especially in Europe," he said, "you can't start putting tariffs on it."

Rather, Europeans had to get their heads around the idea of the Melbourne Cup as a handicap and Australian trainers to get their heads around what it takes to train European horses, Henderson said. Both were in train; the last two Cups have been won by European horses trained in Australia. Now Australian breeders had to return to their historic calling, developing more stayers and fewer sprinters.

Henderson loves to travel, unlike O'Donnell, and so does most of the faraway work. Francesca Cumani acts as European agent, or did until marrying an Australian three months ago. Identifying and buying racehorses is a capricious business, to say the least.

Henderson said OTI had learned mostly from its mistakes. "We've had some corkers," he said. "When we first started off, we chased European form. That was a mistake. Many good stayers in Europe, where they race with a certain tempo, simply are not suitable to Australia. We bought too many like that."

Always, they had one eye on the Cup, but they bought for mile races (1600 metres) and above. "Ironically enough, some weren't bought as stayers; they just developed that way," said Henderson. "Horses like Brambles and Lidari we bought as middle distance horses, but they progressed."

Slowly, Henderson hit on a Moneyball type formula: temperament, good feet, good bones and joints, "the ability to dash off a couple of very fast furlongs", to suit the staccato style of Australian racing. It mattered that European horses were better bred, but also that they were more delicate. Young horses they put on ice for a year.

"We also learnt to forget about the price when you're buying a horse," he said. "Look at its characteristics. Try to imagine him in the Australian environment." None of OTI's four/five in Tuesday's Cup came at an exorbitant price, Henderson said.

Gatewood is the best, Au Revoir and Lord Van Percy still emerging. Lidari was bought to run mile races and suddenly was in a two-miler. Sentimentally, Henderson's heart is with Brambles, who spent two years out of racing because of tendon injuries, but had been nursed back to health by a former trotting trainer who Henderson first met in New Zealand when he was a teenager.

"He was written off, and now he's back in the Derby and the Cup," he said. "Even if there's not perfect success at the end of it, I just love that part of it."

Of course, not every tale is fairy. A few years ago, OTI paid handsomely for a horse called Short Pause, figuring to have a Cup winner. It never settled in the city, was passed on to one country trainer, then another, won the non-TAB Woodend Cup, then went jumping. "It just wasn't to be," Henderson said.

None the less, Henderson still loves the "sheer challenge" of finding a good horse, and the paternal satisfaction he feels when the two-year-old colt that caught his beady eye one day in a paddock in France wins a classic in Melbourne.

Most of all, he remembers the shiver he felt merely to have a runner in the Melbourne Cup for the first time, and the pleasure he feels now taking others on that journey. "The other day, one of the guys in Doriemus rang to ask if he could borrow the Cup for a function," he said. "It was 19 years ago. It never goes away."

Then Henderson was off to pick up a mate who is a Redemptorist priest, not because his life was about to pass before his eyes, but because the priest is chaplain to a Sydney race club, and the pair had rites to observe - but not last.

The ultimate racing guide with the latest information on fields, form, tips, market fluctuations and odds, available on mobile, tablet and desktop.