Jimmy Cassidy joins Who’s The Boss? for a huge Caulfield Cup and Everest preview!

2025-10-15

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Join Adam Peacock and Glen Boss for a lively and insightful conversation with Jim Cassidy in a live show from the Woodstock Hotel, Rooty Hill.Jim takes us through his extraordinary journey in the sport, from his early days in New Zealand to becoming one of Australia’s most celebrated riders. He reflects on his incredible career in the saddle, including his two Melbourne Cup triumphs, his partnerships with some of racing’s greatest horses, and the fierce rivalries and unforgettable moments that defined his legacy on the tra...

Join Adam Peacock and Glen Boss for a lively and insightful conversation with Jim Cassidy in a live show from the Woodstock Hotel, Rooty Hill.

Jim takes us through his extraordinary journey in the sport, from his early days in New Zealand to becoming one of Australia’s most celebrated riders. He reflects on his incredible career in the saddle, including his two Melbourne Cup triumphs, his partnerships with some of racing’s greatest horses, and the fierce rivalries and unforgettable moments that defined his legacy on the track.

With two of the biggest race days of the year approaching, Adam, Bossy, and Jim deliver a huge Raceday Preview for The Everest and the Caulfield Cup — breaking down the key runners, form lines, and storylines in what promises to be a massive weekend of Australian racing.

00:00 Live from Woodstock Hotel

01:35 Racing season

03:15 Evolution of the Everest

05:00 Caulfield Cup

06:00 Current era of racing

09:00 Rumours on horses

14:45 Why Jimmy picks Ka Ying Rising

16:25 The 1200m at Randwick

18:00 Dangers in the Everest

26:20 King Charles Stakes

30:00 Caulfield Cup preview

36:17 Jimmy Cassidy on Might n Power