Glenn Boss has won just about everything there is to win in Australian racing, most famously claiming a Melbourne Cup three-peat aboard Makybe Diva

His feats with ‘the Diva’ were supplemented by a swathe of big-race wins, including four Cox Plates, and two Golden Slippers to boot. More than 52 of his 90 Group One successes occurred in the Harbour City of Sydney. He was renowned for his craft in the time-honoured Doncaster Mile (or Handicap, as it was long known), winning it seven times; the first in 1996 (Sprint By), the last some 23 years later (Brutal).

Boss began his career in professional racing with a tenure under Gympie trainer Terry Chinner. That was in 1984, and the then 15-year-old enjoyed such success on the Gympie circuit that within eight months he had relocated to an apprenticeship under Kaye Tinsley on the Gold Coast. Boss is born and bred Queensland, growing up in Beaudesert, Gympie and Caboolture. He was raised on honest, country values, which stood him in good stead throughout much of his later riding career. On the Gold Coast, he delivered two apprentice premierships and stamped himself as a name of the future. One of the best horses he rode early was Rancho Classic, on whom he won the 1990 Listed Hawkesbury Gold Cup

In 1994, Boss relocated from Queensland to Sydney, to a jockeys’ room he would later describe as one of the toughest in the world. Within a short time, he was riding for Gai Waterhouse, Bart Cummings and Les Bridge, and his associations were strong with Clarry Connors and Jack Denham. That year, he won his first Group 1 race aboard the Star Way horse Telesto (NZ), and the following year he won the G1 Golden Slipper (his first of two) aboard Flying Spur. In fact, the 1995/96 racing season was one of the best for young Boss when he rode four Group 1 winners, including Intergaze in the G1 Champagne Stakes. Since those early beginnings, Glen Boss carved out an auspicious career as one of the best race-riders in Australia, and he tempered his years with bouts of riding in south-east Asia, including Hong Kong, Singapore and Macau. He first went to Hong Kong in 1997 where he learned a lot of things, but in particular his style of riding. ‘Sit quiet and still. Concentrate on balance and rhythm. Keep the stick to a minimum'

Returning to Sydney, he was calmer and wiser, and it kicked off the biggest years of his career. He defeated Northerly aboard the Guy Walter-trained Republic Lass in the G1 Ranvet Stakes of 2003, and he piloted Choisir to victory in the G1 Lightning Stakes.

In this era, his Group 1 wins occurred aboard such horses as Private Steer, Starcraft (NZ), Shogun Lodge and Show A Heart. And, with the spring of 2003 came the first of the Makybe Diva Melbourne Cups, a famous trio of wins that is unlikely to ever be replicated. The pair won the Sydney Cup, Cox Plate, The BMW, Australian Cup and three Melbourne Cups, all between 2003 and 2005.

Still, the success continued for Boss with Group 1 wins aboard Racing To Win, Haradasun, Typhoon Tracy and Turffontein. In 2009, he won the G1 Cox Plate aboard Bart Cummings’ So You Think (NZ), the first of the horse’s two. He won the G1 All Aged Stakes in 2011 aboard Hay List and three Group Ones aboard Ocean Park (NZ), and in 2019 he won the G1 Epsom Handicap and G1 Doncaster Mile before the Newmarket Handicap, Sydney Cup and Cox Plate of 2020.

Boss took his Group One tally into the 90s in 2021, courtesy of wins aboard Think It Over (George Ryder) and Sir Dragonet (Tancred Stakes), who last year carried the champion hoop to his fourth Cox Plate victory. Boss' career in the saddle was very nearly cut short due to injuries sustained in a fall in Macau in 2002. He broke his neck but only narrowly avoided being paralysed. Just months later, he won the Toorak Handicap aboard Shot Of Thunder for trainer John O'Shea.

The following year the Makybe Diva trilogy would begin, catapulting his name into the history books of Australia's most famous race. Another fall in 2011,  when riding the ill-fated Golden Slipper winner Crystal Lily in a Flemington jump-out, cost him the ride on Smart Missile in the Sir Rupert Clarke Stakes. 

After 37 years, Glenn Boss stunned many by announcing his retirement. And to think, it all started off with Boss riding Quarter Horses out in the bush...