Glen Boss is riding the crest of a wave like no other, consolidating himself in the Sydney jockeys room after several years away.

Boss moved to Victoria and then Singapore before deciding to return to Australia after his fly in-fly out victory on Brutal in the Doncaster Mile in April.

He has again made Sydney home and celebrated a momentous victory on Yes Yes Yes in Saturday's $14 million Everest.

While the result of the race was decisive, Boss' participation was a close call.

The jockey revealed it came down to a matter of hours whether he would ride in the Caulfield Cup or at Randwick on Saturday.

He was in line for the ride on Caulfield Cup runner-up Vow And Declare before trainer Chris Waller's decision to run three-year-old colt Yes Yes Yes in his stable slot in the Everest.

“I asked if they could give me 24 hours for a decision on Vow And Declare,” Boss told Sky Racing.

“In the meantime Craig Williams ran for the ride and he was booked and then the ride on the colt came up.”

At the age of 50, Boss can still ride lighter than most and was comfortable with the colt's 53.5kg.

The Hall of Fame jockey is most famous for winning three Melbourne Cups on Makybe Diva but ranks The Everest a highlight.

“The Everest is right up there with the best things I've ever done on a racetrack,” he said.

“What I felt yesterday I'm still coming to grips with.

“You can tell when you walk on the track it's very different.

“I'm living the dream right now.

“I am re-energised and reinvigorated and in a good head space and physically great.”

Boss has been booked to ride Constantinople in the Melbourne Cup after the horse's luckless fourth in the Caulfield Cup for Luke Nolen.

Like Yes Yes Yes, Constantinople is co-owned by Coolmore and is a future stallion prospect.