“It’s been a fascinating, interesting, and emotional journey – and an expensive one!” Bill Simpson’s summary of his ownership experiences will resonate with plenty of other owners in a sport where events rarely turn out as planned.

Simpson was at last month’s Qatar Goodwood Festival – better known as Glorious Goodwood – when a plan did come together perfectly, as his redoubtable eight-year-old Master Milliner saw off 17 rivals to take a valuable two-and-a-half-mile handicap in decisive fashion.

It was a victory that meant a lot to his owner; Master Milliner had previously raced in the name of Bill’s wife Jennie – her colours had previously belonged to Lord Gainsborough – who passed away in December.

He says: “My wife was diagnosed with motor neurone disease in March last year. My focus was on distraction – anything to distract Jennie from the reality of her condition.

“We bought a horse at the sales, Silver Ghost, who has run four good races this year and will make a good three-year-old next season. I’ve also reserved the name Jennie’s Girl for a homebred yearling.

Goodwood was fabulous.

“I had four or five friends with me to watch Master Milliner and they were all in tears after the race. It’s been an emotionally draining time – but Goodwood was fabulous.”

Simpson’s initial interest in horseracing was triggered during childhood visits to local track Taunton with his father and sisters, but it wasn’t until his working life began as a chartered surveyor that thoroughbreds really came into his life.

His first job was with the Inland Revenue – one day he was asked to assess a rating appeal on a trainer’s gallops. The National Trainers’ Federation (NTF) was acting for the trainer and when the case had finished, the NTF asked Simpson to act as its property consultant. He agreed to take on the role.

“That’s how it all started for me,” he says. “I would visit training yards all over the country – in Newmarket, the likes of John Gosden, Sir Mark Prescott and William Haggas, Tony Newcombe down in the West Country and the Easterbys in the north.

“It was while I was at Mark Tompkins’ stable that I saw this beautiful grey horse called Joe The Coat. ‘Take a share!’ he said – so we did!

“However, Mark’s favourite racecourse was Yarmouth, which wasn’t convenient for us as we lived near Hungerford, so we then became owners with Peter Makin and Eve Johnson Houghton.

“When Emma Lavelle bought Peter Makin’s yard, I rang her and asked if she would be interested in training some Flat horses. She said yes. I was planning to send her one horse, Vixen, who was previously with Eve, but the horsebox turned up with Master Milliner too!

“For last few years I’ve been one of the only Flat owners in the stable. I’ve enjoyed the relationship – she’s a very good trainer – and she charges less than Flat-only trainers. That’s really what makes it all possible.”

Master Milliner’s Goodwood strike was his ninth career victory – not bad for a horse who was on the sidelines for 21 months with a tendon injury and suffered severe health problems in his younger days.

“He had meningitis as a two-year-old,” Simpson explains. “He was in hospital for ten days.

“Bobby McEwen, a very good vet, helped him pull through. I think only around 5% of horses get through meningitis.

“Master Milliner’s half-brother, Silver Ghost, was also talented and rated 94, but sadly he died of colic.”

Simpson is referring to the first Silver Ghost, a Dark Angel gelding who won three races in 2017.

Fast forward to the present and the owner has a second runner named Silver Ghost, this one a two-year-old daughter of Phoenix Of Spain who has been placed on three occasions and looks like making up into a decent performer.

Equally exciting, if not more so, is fellow juvenile Silver Wraith, a Havana Grey filly who made a hugely promising debut at Sandown in July, finishing a never-nearer fourth having endured a troubled passage on the sprint track.

Silver Wraith is Simpson’s first homebred to race, being out of the Showcasing mare Resolute Bay, who was in training with Lavelle but never made the racecourse.

Simpson says: “Resolute Bay suffered a stress fracture of her pelvis, so we took the decision when she was three to breed from her. I did the Havana Grey [nomination] deal for £4,000 – which was very fortunate!

“She also has a yearling by Ulysses – that’s Jennie’s Girl – and is in foal to Sergei Prokofiev.

“Silver Wraith and Silver Ghost are models of Rolls-Royce. I think a horse deserves a nice name – and you can’t get better than a Rolls-Royce!”

It’s horsepower of a different kind, however, that is occupying Simpson’s thoughts, with Master Milliner a possible for the Cesarewitch in October. His latest triumph at Goodwood may have been his most valuable, but not necessarily the most magical for his owner.

Did Frank Sinatra pay to entertain audiences in Las Vegas, hoping to get some moneyback?

“Funnily enough, I think that first win at Bath, in September 2020, stands out the most,” Simpson relates. “It was during Covid, so nobody was there.

“When we sent Master Milliner to Emma’s yard [after one race where he was beaten 33 lengths] I asked her if he was going to make a racehorse. She said she wasn’t sure, which was very honest!

“He was/is a big, long, rangy horse – you’d have looked at him and asked, what assets has he got? He relishes two and a half miles on the Flat and wouldn’t make a hurdler as he has a daisy-cutting action and wants quick ground.”

With Master Milliner maintaining his form at the age of eight – “touch wood he’ll carry on next year” – and two smart fillies to look forward to, plus homebred runners to come, Simpson looks set for many more exciting days in the sport.

One side of ownership he would like to see addressed concerns entry fees – Master Milliner not taking up an engagement at York saw Simpson lose £500, not a huge amount, but unwelcome when set against all the other costs owners face.

“Did Frank Sinatra pay to entertain audiences in Las Vegas, hoping to get something back on a good night?” Simpson says. “I lost £500 because Master Milliner wasn’t declared for York, as my trainer said he wasn’t himself.

“A decent win is always welcome – I received around £30,000 after Goodwood, but in the context of the number of horses I own the money only plugs a hole temporarily.

“Who benefits from my horses running? The racecourses and the bookmakers. We’re sending runners to entertain and being charged for the privilege.

“If owners stood up and said entry fees are nonsense, perhaps something could be done.”

Food for thought.