The Sydney Championships are here, and Who’s The Boss? is back with a special episode featuring one of racing’s most iconic jockeys - Jimmy “The Pumper” Cassidy.

Bossy and Jimmy sit down with Adam to relive their greatest Sydney racing moments, from Doncaster Mile glory to Derby heartbreaks. They swap stories of massive wins, near misses, and the legendary figures they rode for - including Bart Cummings, TJ Smith, and Gai Waterhouse. 

With $25 million in prize money on the line and a world-class field descending on Royal Randwick, we break down the history, the rivalries, and the magic of Sydney’s Grand Finals of racing.

So settle in, and enjoy this Sydney Champs special of Who’s The Boss?

Time Stamps

[00:00:00] - Welcome to Who's the Boss!

Introduction to the show and the excitement of race day.

[00:02:20] - Guest Introduction: Jim Cassidy Joins In

Introduction of special guest Jim Cassidy and his insights into racing.

[00:05:00] - Race Day Rituals: Preparing for the Big Event

Discussion on personal routines and preparations of jockeys for race day.

[00:08:30] - The Unique Challenges of Randwick Racecourse

Insights into navigating the track and key elements that influence racing outcomes.

[00:11:45] - Memorable Stories: Legends of Sydney Racing

Sharing personal anecdotes and experiences from legendary trainer TJ Smith.

[00:16:30] - Spotlight on the Doncaster: Key Horses and Predictions

A deep dive into the Doncaster race, discussing contenders and their chances.

[00:20:00] - Derby Day Insights: What Makes It Special

Exploring the significance of Derby Day and the unique aspects of the race.

[00:25:15] - Tips for Success: Jockey Strategies for Winning Races

Expert advice on strategies jockeys employ to ensure successful rides.

[00:29:30] - Special Guest Conversation: Memorable Derby Moments

Engaging discussion about notable moments experienced in past Derbys.

[00:33:00] - Closing Thoughts: Final Tips & Predictions for the Races

Wrap-up of key points from the episode and predictions ahead of the races.

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