Oliver Sherwood compared to Fred Winter as former jockeys pay tribute to Grand National-winning trainer

Leighton Aspell, who rode more than 200 winners for Oliver Sherwood, including 2015 Grand National hero Many Clouds, hailed the trainer for his attention to detail and patience with horses following the announcement he will soon be handing in his licence. 

Sherwood said on Monday that he will send out his final runners at the end of the summer and become assistant to Harry Derham, and the man who partnered his biggest winner praised his influence on his own career in the saddle.

Aspell, who retired from race-riding in 2020 having ridden 232 winners for Sherwood, said: "He's been great and we had many, many good years. He was brilliant to ride for, he made my life easy and just gave me so much confidence. I'd say I had more confidence in my last ten years than I ever did – and a lot of that was because of Oliver. He's a great trainer and a great friend too, he always had your back."

Undoubtedly the highlight in more than a decade associated with Sherwood was the incredible 2014-15 season with Many Clouds, which included Hennessy Gold Cup success before their crowning moment in the 2015 Grand National at Aintree.

"With Many Clouds, Oliver just gave him so much time to mature and strengthen, and each season when he strengthened he was able to train him harder," Aspell added. "That allowed him to just get better and better. He went exactly the way we wanted to him to go that season."

No rider partnered more winners for Sherwood than Jamie Osborne, who became his stable jockey in the late 1980s. Like Aspell, he credited the master of Rhonehurst for improving his own confidence.

Oliver Sherwood (centre) at Uttoxeter in 1995 with owner Roger Waters and jockey Jamie OsborneCredit: Phil Smith

Osborne, now a Flat trainer in Lambourn, said: "The stable jockey job was perfect for me as he was such a gentleman. It came at an interesting time because I hadn't ridden too many winners and I remember Nicky Henderson was dangling the carrot too. I had a very enjoyable riding career.

"When I started I lacked experience and in the first year I may have frustrated him quite a bit, but we ended up having plenty of winners and had the utmost trust in each other. The way he campaigned his horses meant they just kept improving, and he was brilliant at getting his horses to build up sequences."

Simon Sherwood rode for his brother for a number of years and feels his sibling has had made the right decision, stressing training had become a "numbers game" when Oliver was instead best when focusing on a smaller string.

Simon, who rode a Cheltenham Festival double in 1988 for Oliver on Rebel Song and The West Awake, said: "He had an incredible career and was in the top five trainers in the country at one point. He was very Fred Winter-esque in his level of detail and he achieved everything a trainer could achieve. It's just a different game now."

Reflecting on their jockey-trainer relationship, Simon added: "I'd turn up late, which would annoy him a lot when we worked together, but I can only recall one cross word between us. It was at Newbury and I'd ridden a horse called Kodiak Island, who we fancied. He finished second and as I walked in I could tell by how he was looking at me that he wasn't happy.

"I got asked about the race by, I think, Brough Scott or John Oaksey and replied 'my brother has joined the league of ignorant trainers' – he gave me a right bollocking after that. Other than that there wasn't a bad word said and we had some fantastic times."

Read these next:

Grand National-winning trainer Oliver Sherwood to end near 40-year career and become assistant to Harry Derham 

Hats off to one of the sport's good guys, universally liked but also respected in equal measure 

A Grand National hero and a two-time Cheltenham Festival winner: four of Oliver Sherwood's best horses 

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