Chianti Classico gave the Cotswolds-based trainer his sixth Festival winner at last year's meeting before suffering a career-threatening injury when attempting to advance his Gold Cup claims at the track in December.
Losing your stable star in his prime is enough to make a grown man cry but it was youngest son Archie who had Bailey in floods of tears.
The 19-year-old made his County Championship debut for Gloucestershire at Lord's in September when the fast bowler bagged four wickets in front of his emotional dad.
Cricket-mad Bailey said: “When the fixture list came out in April I asked Archie when he thought he might make his debut and he said Lord's. He did that because he knew I would cry.
“It's every cricketer’s dream to make your debut there. I used to play for the MCC but I never played at Lord's. I got more text messages after that than I did after Chianti Classico won at Cheltenham.
“I had a caricature done and gave it to Archie for Christmas - him with the ball and me in floods of tears.
“Most of my cricket was played with Oliver Sherwood - we set up a team in Lambourn and played a lot of charity games. I played against Viv Richards and Ian Botham.”
There was also a lot for Bailey to be proud of at last year’s Cheltenham Festival. He saddled two runners in the Ultima Chase - a race he had won 24 years earlier with Betty's Boy.
Things did not start well with Trelawne falling at the second but everything went to plan for Chianti Classico. He ran out a taking winner (below, with David Bass) to give Bailey dreams of a second Gold Cup after Master Oats' success 30 years ago.
The eight-year-old gave the trainer his 1,500th career winner when making a successful return to action at Ascot. The victory prompted Bailey to fulfil a promise of putting his long-time assis...
Losing your stable star in his prime is enough to make a grown man cry but it was youngest son Archie who had Bailey in floods of tears.
The 19-year-old made his County Championship debut for Gloucestershire at Lord's in September when the fast bowler bagged four wickets in front of his emotional dad.
Cricket-mad Bailey said: “When the fixture list came out in April I asked Archie when he thought he might make his debut and he said Lord's. He did that because he knew I would cry.
“It's every cricketer’s dream to make your debut there. I used to play for the MCC but I never played at Lord's. I got more text messages after that than I did after Chianti Classico won at Cheltenham.
“I had a caricature done and gave it to Archie for Christmas - him with the ball and me in floods of tears.
“Most of my cricket was played with Oliver Sherwood - we set up a team in Lambourn and played a lot of charity games. I played against Viv Richards and Ian Botham.”
There was also a lot for Bailey to be proud of at last year’s Cheltenham Festival. He saddled two runners in the Ultima Chase - a race he had won 24 years earlier with Betty's Boy.
Things did not start well with Trelawne falling at the second but everything went to plan for Chianti Classico. He ran out a taking winner (below, with David Bass) to give Bailey dreams of a second Gold Cup after Master Oats' success 30 years ago.
The eight-year-old gave the trainer his 1,500th career winner when making a successful return to action at Ascot. The victory prompted Bailey to fulfil a promise of putting his long-time assis...
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Daily Record (Digital) - 1 Issue, March 11, 2025