The 26-year-old backrow forward from Charters Settlement, N.B., signed with London Irish last year, joining the Aviva Premiership side in England after last fall's World Cup. Then last month, he was loaned to South Africa's Stormers to play Super Rugby.
It doesn't get any better in club rugby circles.
Southern Hemisphere rugby rules and Super Rugby is the elite club level there, covering South Africa, Australia and New Zealand. In the Northern Hemisphere, the French Top 14 may be the only league that rivals England's.
"It's been a whirlwind for the last couple of months, for sure," said Sinclair, who will start for Canada against Italy on Friday night at Toronto's BMO Field.
The six-foot-four 238-pounder benefited from a backrow injury crisis that sidelined Springboks star Schalk Burger as well as Duane Vermeulen, Nick Koster and Nizaam Carr. Stormers back coach Robbie Fleck, who has contacts with London Irish, contacted the English team to see if they had any players who could help them out.
Sinclair's playing time with London Irish had been limited by a thumb injury, and a change in club management. But the Canadian was healthy again when the South African call for help came and Brian Smith, London Irish's director of rugby, put Sinclair's name forward.
Unbeknownst to Sinclair, the Stormers started studying him on video — and liked what they saw.
He came into London Irish for a weight training session on May 8 and got the news.
"That was 10 a.m. and by 7 p.m. that night I was on a plane," he said.
Sinclair, one of Canada's so-called beardos at the World Cup because of his then luxuriant facial hair, ran through a gamut of emotions as he waited to take off.
"Exited for sure. Nervous, definitely. Like I had no time to look into the team or watch any of their games closely to kind of get a feel for the team. I was going in there blind for sure. But that was part of the excitement for me."
Sinclair had only one practice under his belt before dressing as a substitute against the Cheetahs. Fifteen minutes into the game, an injury brought him on the field.
He has started the three games since, against the Waratahs, Sharks and Bulls with the last two being high-profile South Africa derby matches.
"He's played some big rugby," said Canadian national team coach Kieran Crowley, a former All Black.
A 19-14 road win against a Bulls side that contained 11 Springboks came before 55,000 at famed Loftus Versfeld Stadium in Pretoria.
Sinclair, the only non-South African on the Stormers roster, has tried to keep everything in focus.
"I just have to do my little part and make sure I keep my mistakes to a minimum. And the rest of the guys will look after the win, really."
His teammates include Springboks captain Jean De Villiers and star winger Bryan Habana.
Former Canadian captain Gareth Rees, now manager of the Canadian men's program, agrees that Sinclair is blazing a path.
"I said to the players when we welcomed him in the squad — because he arrived a few days late because he had been playing for the Stormers — he's broken the glass ceiling in terms of Super 15 rugby," Rees said.
In the 1990s, former Canadian international Christian Stewart played for Western Province and also the Springboks. But he had South African bloodlines and Rees sees Sinclair as the first Canadian to make it in Super Rugby.
"A huge achievement for him as an individual," said Rees, who sees Sinclair as living the dream that Rugby Canada wants other players to see.
His Canadian teammates are quick to acknowledge the advantages of playing in Super Rugby.
"He's bringing back a bit of a new edge to himself," said winger Sean Duke. "Hopefully we can feed off that and hopefully he can teach some of the guys a few things. I'm sure he's more than willing."
Crowley knows the difficulties Canadians face in getting any overseas contract, let alone a Super Rugby gig.
Often times the import restriction is two foreigners. "And our players are competing against New Zealanders and Australians for those positions," Crowley said.
"I think we have a lot of players that could easily play at the top level but because they're Canadian they're not perceived as having that ability, which is unfortunate for them.
"So it's a slow process. It's good to see guys like Jebb Sinclair getting his opportunity. There's other boys signing, so we're keeping at it and trying to support guys as much as we can to get these opportunities."
Sinclair says it's hard to compare the English league to Super Rugby, for the weather and schedule if nothing else.
The English league is a grind, with more games to start with and the total growing from various cup competitions. Plus there is inclement weather.
Super Rugby is shorter but more intense.
"Both leagues view themselves as the premier leagues in the world. But you know it's too tough to call really," Sinclair said. "But from my view of it, the first four games with the Stormers were faster than anything I've played."
A plus of playing for the Stormers is being based in Cape Town.
"It's unbelievable. Nicest city I've ever been to," said Sinclair, who returns to South Africa for five more weeks after his current international duty with Canada.