Located just a short flight away from one of his homes in New York City, Montreal was often on the late American sex offender Jeffrey Epstein’s radar.

Though it’s unclear whether Epstein visited Quebec after he was convicted in 2008 for soliciting sex from a minor and another prostitution charge, and was registered as a sex offender, the disgraced financier didn’t shy away from planning trips to its biggest city.

Epstein’s assistant twice reserved a room for him at the Ritz-Carlton in July 2014 when he tried to catch the Nasty Show at Montreal’s Just for Laughs Festival, before ultimately cancelling, according to emails released by the U.S. Department of Justice last month.

Many of the hundreds of times Montreal and Quebec are mentioned in the so-called Epstein files are largely insignificant.

One person writes to Epstein saying they’re in Montreal to learn French and hope they “don’t pick up the Quebecois accent.” In another email exchange, Epstein qualifies Montreal as the second best place to learn French and enjoy singledom, after Saint-Barthélemy in the Caribbean.

Since the release of the files, prominent people – from the Clintons to university professors – have faced scrutiny over —  and have had to defend —  their association with Epstein, be it personal or business, especially after his 2008 guilty plea.

Here are some Quebecers who have found themselves in that position.

Investment, talks of ‘Sharia coin’ with entrepreneur

Montreal crypto entrepreneur and angel investor Austin Hill notably reached out to and met with Epstein several times over four years, including at the multimillionaire’s private island, Little St. James, in April 2014. According to emails, Hill and his group stayed at an off-island hotel during that visit.

The two men first met a month prior at the Fairmount Pacific Rim in Vancouver, after which Epstein invested $500,000 in Hill’s cryptocurrency then-startup Blockstream through a venture fund.

Over the next few years, according to the files, Hill reached out seeking Epstein’s advice and connections. In January 2015, as news of then prince Andrew’s friendship with Epstein began circulating, Hill wrote Epstein apologizing for “interrupting in what I’m sure is a crazy media storm for you & your team” to ask for his advice and counsel on “a few things both business, Bitcoin, personal & esoteric mind games that we play.”

The previous month, Virginia Giuffre, one of Epstein’s accusers who has since died by suicide, alleged in a Florida court that she was trafficked and forced to have sex with Andrew Mountbatten-Windsor when she was 17.

On Thursday, Mountbatten-Windsor was arrested on suspicion of misconduct in public office for his connection to Epstein. He was released from custody the same day under investigation, police said, meaning he has neither been charged nor exonerated. He has previously denied all wrongdoing.

Hill and Epstein’s correspondence, at least as far as the Epstein files go, ends in 2018 when Hill suggests they set up “some secure communication.” At that point in time, they were in serious discussions to create a “[S]haria compliant coin” for Muslim clients.

In an emailed statement to CBC News, Hill said his interactions with Epstein occurred “in the context of fundraising introductions.”

“At the time of these interactions, he was widely regarded as a legitimate, well-connected figure and many trusted associates vouched for him,” he said.

Hill said his communications with Epstein after he left Blockchain in 2016 were “sporadic” and “limited” on technology-related topics.

“By mid-2018, I was no longer actively involved in the fintech or Bitcoin scenes, and no longer had business reasons for continued contact with Epstein. I had already ceased contact by the time his crimes became fully public,” he said. “I regret any association with him, I stand with the victims, and I support full transparency and accountability so that all responsible parties are brought to justice.”

Guy Laliberté tried to sell Epstein his villa

Another Quebecer whose name comes up more than once in Epstein’s inbox is businessman and Cirque du Soleil founder Guy Laliberté.

The emails started in 2011 and, over the years, included a Christmas card and an invite to a charity event where Laliberté called Epstein one of his “dear friends.”

A spokesperson for Laliberté, Anne Dongois, told CBC News the emails are “not really personal” and are more so “mass mailing emails.”

In 2018, Laliberté also tried to sell Epstein two of his villas in Ibiza, according to the files, but the sale didn’t go forward. Dongois said the email with that proposal was crafted by Laliberté’s communications team and sent to about 25 people who could afford it, essentially.

Laliberté’s appearance in the files has also been reported in Le Journal de Montréal and La Presse.

Dongois said the two men didn’t know each other personally beyond a handshake here and there at social events in New York, and that Laliberté has never been to Epstein’s home.

“[Laliberté] has a very, like, heavy address book. So Epstein was in his address book and he received the mass mailing Christmas cards and a few communications that he sends to all his contacts,” said Dongois.

As for the “dear friends” reference, Dongois says that email was also crafted by Laliberté’s team and sent to thousands of people.

Quebec’s pension fund rethinks link with Emirati tycoon

Montreal also comes up in the Epstein files so often due to the many visits Sultan Ahmed bin Sulayem paid the city. The Dubai tycoon previously headed the portuary terminal operator DP World, which partners on projects with Quebec’s pension fund manager, La Caisse de dépôt et placement du Québec (CDPQ).

Bin Sulayem announced his resignation from the company last Friday after several emails – many of which contained explicit content – linked him with Epstein.

In November 2016, bin Sulayem told Epstein of his “big day in Canada” which took place in Montreal, after which DP World and CDPQ announced the launch of their $5-billion investment platform. Bin Sulayem flew to Epstein’s private island right after finalizing the deal with the CDPQ.

The correspondence between Epstein and bin Sulayem included crude jokes, links to profiles on Seeking Arrangements, a website known for connecting people with so-called “sugar daddies,” a poem about Brazilian women, and the pricing for an explicit massage bin Sulayem said he received while in Tokyo.

Bin Sulayem also initiated the transfer of a masseuse, who worked at Epstein’s private spa, to a spa in Turkey “so she gains better experience.”

After the messages between bin Sulayem and Epstein emerged, the CDPQ paused “additional capital deployment alongside” DP World and demanded the company “take the necessary actions.”

“The company took the appropriate measures. We will move quickly to work with DP World’s new leadership to continue our partnership on port projects around the world,” a spokesperson for the CDPQ, Jean-Benoît Houde, told CBC News in a statement.

The Port of Montreal says it is also continuing its work in light of bin Sulayem’s departure.