Now his son, Tim, has a chaser who is reawakening memories of the glory glory days of Night Nurse, Sea Pigeon, Alverton and Little Owl.
"I wouldn't say I'm superstitious," Tim Easterby says, "but I don't like tempting providence."
And who can blame him, when he has a horse like Simply Dashing to look after in only his second season with a training licence. It is why he will look no further than today's outing in the Tripleprint Gold Cup at Cheltenham when discussing plans for the six-year-old chaser, but he cannot stop others doing it for him.
Simply Dashing is already a 14-1 chance for the Cheltenham Gold Cup. By this evening, he could conceivably be the favourite.
It is quite a responsibility for one so young, and that goes for both trainer and horse. It is fortunate, then, that steeplechasers do not understand ante-post betting, while Easterby has a wealth of experience to call upon.
He inherited the licence at Habton Grange Stables in Malton from his father, Peter, the only man to train 1,000 winners both on the Flat and over jumps, and while it is now Tim's initials on the saddlecloths, the operation remains a family business.
Tim learnt the trade as his father's assistant for several years, and there was never any question that, when the time came, he might strike out in a yard of his own. "I didn't ever think about anywhere else," he says. "This is the family concern, it's what I've been brought up with and it's what I've always wanted to do."
The internal promotion to the role of licence holder was well-timed, because business is on the up for Easterby & Son, Racehorse Trainers. For more than a decade, Great Habton has produced lots of winners, but no headline-grabber of a horse to equal Sea Pigeon, Night Nurse, Alverton or Little Owl.
Simply Dashing, at long last, could be the one, judged on his admirable performance under top weight in the First National Bank Chase at Ascot last month. A horrible blunder at the ninth fence seemed to have ruled him out of contention with a mile still to run, but he recovered to win as he pleased.
"When he made that mistake, I said to myself, `just come back in one piece now and it will be all right, there'll be another day'," Easterby says. "I was so impressed with the way he came back on to the bridle. He's got such a big heart, and they were some useful horses he was giving weight to. Horses like that are very hard to find."
For much of the last week, the exact destination for Simply Dashing this afternoon was unclear, with the Tommy Whittle Chase at Haydock a serious alternative, but anyone looking for evidence of a rift between father and son will be disappointed.
"We always get on very well and we make all the decisions together," Tim says. "We discussed everything and decided that this was the best race for him."
But just suppose, for the sake of argument, that he had favoured Haydock while his father was determined to go to Cheltenham? He pauses, considers, but the leap of imagination is too great. "It wouldn't happen," he says. "A situation like that would simply never occur."
It is a comfortable blending of the generations which many families would envy, and it extends too to the sales ring. This, even more than the racecourse, is the natural habitat of an Easterby - and both Peter and his brother, Mick, are famous for their ability not just to buy a bargain, but to then find an owner to pay for its upkeep too.
Their legacy is in good hands. "I really enjoy the sales," he says. "There's no set rules to how we buy horses, sometimes we'll go round together, other times father will buy a horse or I will, but we find that we tend to like the same sort of horses. It's just down to instinct, and keeping an open mind."
An economy with words is another family trait which Tim has inherited in abundance, particularly when it comes to planning ahead. He would not be normal if he did not have at least the rough sketch of a route to Cheltenham next March mapped out in his mind, but nothing short of thumbscrews could persuade him to discuss it.
Then again, he has been here before, barely two months after he inherited the Great Habton licence.
When Scotton Banks won the Martell Cup at Aintree in 1996, he too was a seven-year-old, as Simply Dashing will be next spring, and his potential seemed equally limitless. Within a couple of months of the following season, though, his form had collapsed.
"That was a huge disappointment," Easterby says. "We found out in the end that he had a problem with his hind suspensory, and he's sound again now and we hope he'll be hunter chasing this season.
``But you have to be prepared for things like that. You always know that when you're having a good do, there's going to be a bad do to come."
It is quite a spectre to have to banish so early in his training life, but if any horse has the ability to do so, it is Simply Dashing. Supermarkets and chain stores may have taken over the high streets, but on the racecourse at least, a family business is booming.Reuse content