Legendary Melbourne Cup-winning jockey Glen Boss announces retirement


Glen Boss – who rode the Makybe Diva three times in a row in the Melbourne Cup – has announced his retirement after a Caulfield World Cup qualifier this week.

The boss led the Makybe Diva to her three Melbourne Cup victories between 2003 and 2005.

He also won several other prestigious competitions, including Cox Plate, VRC Derby and Golden Slipper.

The final 52-year-old will be Zipping Classic in Caulfield on Saturday.

“This idea is something I’ve been thinking about in the last six months especially in the last two or three months,” Boss told Ladbrokes.

“I’m one of those people who is always 100%, chips by all means, and I promised myself more than a decade ago … completely dedicated by all means, then it was the last time.”

The boss said he began to experience mental stress late in his career.

“I felt as though I had fallen off a cliff,” he says.

“I thought it was a good time because I have a lot of energy and I want to put all that energy into other things, and that’s what I’m doing.”

The winner won the 2020 Cox Plate on Sir Dragonet.(Photos of AAP / Racing: Natasha Morello)

The Boss has won 90 1-team competitions in Australia, marked by their Melbourne Cup victory.

She also won the 2005 Cox Plate on the Makybe Diva, directing So You Think (2009), Ocean Park (2012) and Sir Dragonet (2020) to win the age-old heavyweight bout in the Moonee Valley.

Boss’s success in Sydney also included two Golden Slipper greetings on Flying Spur (1995) and Sebring (2008).

He also rode Yes Yes to win in The Everest in 2019 and in the same year he won with Kolding at the opening of the Golden Eagle.


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