The first of Bossy's four Cox Plates came on champion mare Makybe Diva

The greatest showman forever a 4-time champion at The Valley

By Ben Caluzzi

The ultimate showman. The man for the big occasion, a superstar in the saddle and one of only 47 jockeys ever to be inducted into the Australian Racing Hall of Fame. The legend that is Glen Boss announced his retirement from race riding last week, and while he has since said he will ride in Saudi Arabia as a one-off in February, it is fair to say the 52-year-old lapped up his final day in the Australian sun like only he can at Caulfield last Saturday.

The 90-time Group 1 winning hoop has been everything that is great about racing. He has brought new eyes to the sport, he has been a great entertainer both on and off the track, and while he has often made bold statements that have turned heads in the media – he has frequently backed them up that following Saturday.

There is good reason why Glen Boss has adopted the nickname ‘Group 1 Bossy.’ He has saved his best rides for when they mattered most. Having won four W.S. Cox Plates, he will forever hold a special piece of history here at The Valley, and while we have learnt that his official retirement has been put on standby for now, it is a good opportunity to reflect on those four famous days that shaped a large part of his career.

Boss says he has “only ridden two champions” in his life, so it is fitting that his first two Cox Plate victories came on those two said champions. Makybe Diva was the mare that really took Boss from champion to legend, as Greg Miles famously exclaimed when she crossed the line in her third straight Melbourne Cup.

Before that third Cup though, she reigned supreme in Australia’s Weight-For-Age Championship. The Diva came into the 2005 Cox Plate as the even money favourite, and there was no hiding from the fact she had a sizeable target on her back.

They rode against her, they tried to take off early and put her in an uncomfortable position, but it only played into the hands of the nation’s best stayer as her stamina kicked in, merely toying with her opposition as they turned for home at the 200.

It was a win of a great, summarised perfectly by a jockey who knew his horse all too well, and it put the rubber-stamp on Makybe Diva as one of the greatest horses in Australian Racing history.

In the 2009 Cox Plate we saw the unearthing of a superstar, as Boss partnered the striking three-year-old colt So You Think to victory by leading all the way at luxurious odds of 12/1.

With just 49.5kg on his back, So You Think cruised to the home turn while the chasing pack were hard off the bit, and at that point Glen Boss knew he had his secured his second Cox Plate victory. Boss only rode So You Think twice, but the dual Cox Plate champion is one of the finest winners of the race we have ever seen.

Ocean Park provided Glen Boss with his third Cox Plate win in 2012, and for Boss this was as satisfying as any of them.

Only months earlier, Boss rode Ocean Park for the very first time in the Rosehill Guineas, and even he admits he could be to blame for the loss after a “terrible” ride that saw Ocean Park run second.

Boss later made amends in the best way possible, winning three Group 1’s in a row on Ocean Park later in the year which culminated in a thrilling Cox Plate victory over the star three-year-old All Too Hard.

With the best recent Cox Plate record of any jockey in the last 20 years, it was only fitting that Boss would take out Cox Plate 100 on Irish raider Sir Dragonet in 2020.

With no crowd on course due to the coronavirus pandemic which shook Australia and the world, the images of Boss high in the irons, saluting aboard Sir Dragonet in front of empty grandstands as the 100th edition of our great race will live on forever.

Of course, crowd or no crowd Boss was in his own element and after the seas parted for him and he had Cox Plate four in his keeping he was later quoted, “it felt too easy for me.”

He had earlier told Ciaron Maher and David Eustace before the race that Sir Dragonet would win, but how could he have known? Was it confidence he had in his horse, confidence he had in his own ability, or a mixture of both? Probably the latter, but Boss found himself in the right position at the right time far too often for it to be a coincidence.

A champion jockey and an even better ambassador for racing. We can’t wait to see ‘Bossy’ represent Australia at the Saudi Cup on February 25 in 2022.