Better to have loved and lost (heavily)

Racing for Clay Freud was largely but not exclusively an ambitious, twin-forked search for both the new messiah and the holy grail.

The messiah was the trainer who would win him the Triumph Hurdle, the incredibly competitive race for four-year-olds at Cheltenham, and the grail was the three-year-old gelding, bought off the Flat the previous season, that would take him into the Festival winners' enclosure.

Clay changed trainers more often than some people change their minds. A colleague in the press room only had to say: "So and so's a shrewd judge of a young jumper," and Clay would be phoning the newly discovered genius with a commission to find him a Triumph winner. Or if he watched a new young trainer interview well on TV, he would be lauding this tyro of the turf to anyone who would listen and sending him a horse.

I had a leg, or even two, in a number of Clay's Triumph tilts and the partnership brought endless fun and laughter, but only if you were capable, like him, of laughing at yourself.

A consistent racing foible of his was the unerring ability to part with horses prematurely. He didn't do patience.

One of our contenders showed little promise in his early runs and, against the advice of the trainer, Clay insisted we sell him. We did and five years later Kristoffersen is still winning races.

He became convinced that Orpen Wide, a horse he shared with another good friend Andy Wright, would not jump obstacles and he let himself be bought out. It has since won 14 races, on the Flat and over hurdles and fences, and £138,000 in prize-money.

The nearest we came actually to having a runner in the Triumph was with the gelding Star Protector, who won a good three-year-old hurdle at Ascot then ran well in a trial race at Cheltenham. We were planning how we would celebrate a famous victory when the horse broke a leg on the gallops and had to be shot.

Another of our well-bred hopes managed to get to a racecourse just once before "going wrong". He spent time with three different trainers, each of whom told us regularly that he was just six weeks off a run. When the six weeks had stretched to two years we let the final trainer keep him to settle a month's keep.

One of Clay's better investments was in the Ascot syndicate that owned the Derby winner Motivator. He wasn't totally pleased with the share of pot that came from the victory but it did motivate him to try to win the Derby on his own.

He spent more than he had ever spent on a racehorse (he told me he had been skiing – spending the kids' inheritance) on a yearling that he sent to a fashionable Flat trainer. After an inglorious start to its career the trainer rang him and said he thought they should try it on the allweather. Clay was so incandescent that his Classic candidate should be thought worthy of such lowly company that he immediately took the horse away. It wasn't much good over hurdles either.

Our best adventure was with a filly called Nagnagnag, a cheap two-year-old we bought from Jack Berry. She turned out to be something of a superstarlet, ran at Royal Ascot and won twice at Epsom. We switched trainers (naturally!) for her three-year-old career and had champagne days running her in Group races in France. A few days before she was due to run in a major race at Longchamp the trainer said he'd had an offer of £100,000 for her.

Clay and I had a chat. "Are you short of £50,000 at the moment?" he said. "No," I said. "Are you?"

We convinced each other that we were in it for the fun and glory of success, not the money.

She didn't win another race for us and a year later she fetched £10,000 at Ascot sales.

Charles Wilson is a former editor of 'The Independent'

Freudian tips: Wit and wisdom

Sir Clement Freud wrote regularly in the Racing Post. These extracts give a flavour of his greatly missed column:

On an experience as a jockey: I hadn't realised that jockeys could hear the commentary and the shouts of the punters and the bookmakers. I was so taken with this that I forgot to steer, until I heard a man shout: "Open the gates, he's coming in!"... I got off and found I was too weak to remove the saddle to weigh in, which is not essential when you finish 15th... Why did they dope-test the horse, I wondered, when it was I who was up to the gills with amphetamines and diuretics in order to make under 12st, which God had never intended as my weight?

On turning unofficial bookmaker: My cricket club chartered a plane to take a party to Longchamp for the Arc in 1965 and I went along laden with money – I fancied Sea-Bird a lot. I went to the parade ring to ensure that my fancy was in good shape and found that he was not. He was a dead ringer for a giant shaving brush: sweat ran down his neck, litres of what looked like Greek yoghurt oozed from beneath his saddle. I returned to my party and offered to lay Sea-Bird at pari-mutuel odds: "Save you queuing and I pay out more quickly than the Gauloise smokers behind the windows." I wrote the bets on my racecard: £50 Fred. £65 Angus. £40 Charlie. £3 Charlie's girlfriend... As Sea-Bird paraded the sweat glistened in the afternoon sunlight; when he cantered to the start, specks of white foam flew into the air. I nodded smugly. Sea-Bird won rather comfortably, but I was absolutely right – the people who had not bet with me spent an age waiting to be paid.