Back then McDonald was a 16-year-old kid new to group one racing, Bosson a man at the peak of his powers. It was literally the master and the apprentice.
But even handing out riding lessons Bosson knew the kid had the gift.
"You could tell he was a natural even back then," says Opie.
"Talent like James has doesn't come along very often and even while he was learning he had that gift."
McDonald learned his lessons well. A few years later he bundled up that natural ability, took it to Sydney and is now world class.
Bosson has loved the development of his friend.
"Every time I watch a race in Sydney or during the big carnivals in Aussie I look to see where James is. Everybody is proud of what he has achieved," says Bosson.
Punters here didn't need reminding of that talent but McDonald reminded us anyway at the recent Ellerslie carnival. He had 12 rides for seven winners, four of them in black type races.
He was the punter's Superman.
Today and into tonight at Ellerslie, in the most important race meeting of the season, Superman meets the King Of The Karaka Million, 12 years on from their first lesson. They ride the two favourites in both $1 million races.
Punters will be torn between the local hero and the prodigal son.
When they last clashed at that Christmas carnival Bosson wasn't fit enough, coming off the back of a three week suspension. He couldn't get in the fight.
"But I am ready now," warns Bosson.
"I am fit, I have been losing weight to ride Probabeel and I will get down to 54.5kgs for her on Saturday.
"Losing that weight and seeing horses like Melody Belle and Te Akau Shark (who gallops between races tonight) has got me really excited about the next few months.
"So I'd say I am in form at the moment.
"And I'm really looking forward to this meeting. It is the big one of the year for me."
Considering 1200 horses are sold at Karaka every year it is scarcely believable Bosson has ridden the last three Karaka Million winners, for a combined treble dividend of $396.
Today McDonald is on Play That Song (favourite in the Million) and Conqueror (Classic), Opie on Cool Aza Beel and Probabeel respectively. Because of the wasting to ride Probabeel, they are the only two races Bosson will ride in.
If the markets are right, they could share the spoils.
"Play That Song is very good," says McDonald.
"She has all the weapons. She is fast, has great manners and she has stamina.
"She can hold her sprint for a long time which is rare.
"I like her barrier, it gives me options but she is going to be really hard to beat."
Bosson isn't worried by Cool Aza Beel's campaign detour for his final lead-up race and thinks he can be just off the speed. He says a fourth consecutive Million is possible but respects the favoured filly.
And both men quickly mention Not An Option and Taroni as the dangers and are just as respectful of the talents of the other jockeys they battle tonight.
Their roles are reversed in the Karaka Classic, where Bosson is on the favourite filly and McDonald on the second favourite colt.
Conqueror has decent form in a vintage Australian 3-year-old crop and would usually profile as the horse to beat.
But Probabeel oozes class, looking to become the first winner of both Karaka Million races.
"I worked her Monday and she is where she needs to be," says Bosson.
"I think there could be good tempo in the race and I want to be midfield and then pull to the outside, balance her up and I think she will finish over the top of them."
So does friendship count, out on the track trying to pay a decent chunk off your mortgage?
"No," says Bosson.
"We are good mates, like I am with some other guys, but this is our job. You haven't got time to be thinking about each other. This is a big night and we are all there to win."
JAMES McDONALD
Age: 28
Career group ones: 44
Career stakes: Over $100 million
Ellerslie record: 131 wins at a strike rate of 5.3
Weighty question: How did you get down to 54.5kgs needed today: "I walk about 8kms a day. I like to do it in peace and quiet, no music or podcasts. I use that time to think."
Fun fact: McDonald has ridden a winner at Royal Ascot.
McDonald on Bosson: "He has always been a great rider, hardly ever makes mistakes. He is simply one of the best jockeys New Zealand has ever produced."
OPIE BOSSON
Age: 39
Career group ones: 69
Career stakes: Over $50 million
Ellerslie record: 218 wins at a strike rate of 7.6
Weighty question: How did you get down to 54.5kgs needed today: "I started about three weeks ago, really watching what I eat. Then the last little bit I drop by sitting in a hot bath, usually watching movies."
Fun fact: Bosson is unbeaten in four NZ rides on Probabeel, nobody else has ridden her to win.
Bosson on McDonald: "You could tell he was special when he was riding here but he has become very polished riding overseas. I wish I looked that good in a tight finish."
