Saudi Arabia is opening up its economy and its society. Why has Canada been so slow to capitalize on that?

There are many ways to measure just how much Saudi Arabia has changed in recent years. Bumping into Montreal businessman Sruli Richler at an ancient historic site is one of them.

Richler is an observant Jew, who has a beard and wears a yarmulke under his ball cap.  

He stopped for a visit at the country's former capital Diriyah, just outside Riyadh, which is in the midst of an immense $63-billion US restoration project. 

Just in case the presence of an overtly Jewish man in the staunchly conservative Islamic kingdom caused any friction, Richler jokingly pulls out a "Make America Great Again" cap from his bag — a precaution, he says, in case he wants to blend in quickly with the numerous U.S. visitors.

But by and large, he says he was welcomed graciously throughout Saudi's capital.

"I honestly thought it would be much more hostile," he told CBC News in Riyadh. "Everyone is very calm and very relaxed and it was pleasant to do business."

Richler — a distant cousin to the famous Canadian writer Mordecai and his journalist son Noah — is in what he calls the "reverse logistics" business. That is, his company finds money-making uses for items people return to stores that can't be resold.  

"I'm looking to do business in Saudi. It's an up-and-coming country," he said, of his reconnaissance trip.

"When you land here, you are pleasantly surprised. I believe that when you bring businesses together, it brings people together. It's a road to the future."

But that's not how many other Canadians — including senior members of the current Liberal government — have always viewed the world's second-largest oil producer.

In 2018, Canada's Global Affairs Department, overseen by then-foreign minister Chrystia Freeland, sent out a series of tweets criticizing Saudi Arabia's human rights record and calling for the release of an activist with ties to Canada. 

An enraged Saudi government accused Canada of meddling in its internal affairs. It expelled Canada's ambassador in Riyadh and took the unusual step of freezing trade links between the two countries and ordering thousands of Saudi university students studying in Canada to return home. 

Later that same year, Canada imposed sanctions on 17 Saudis linked to the murder and dismemberment of Jamal Khashoggi, a prominent critic of Saudi leader Crown Prince Mohammed bin Salman. Khashoggi was killed inside the Saudi consulate in Istanbul.

As the deep freeze in relations set in, trade, cultural and political contacts between the two countries became casualties.