The enduring significance of Meghan, Duchess of Sussex's once-close friendship with Canadian socialite Jessica Mulroney has come back into focus. This comes as Jessica and her ex-husband, television host Ben Mulroney, mark the 18th anniversary of their engagement—a union that once defined Toronto high society.
The Toronto Blueprint: Gloss, Strategy, and Access
Meghan Markle met Jessica Mulroney in Toronto in 2011, at a crucial juncture in her life and career. Jessica, then a 34-year-old fashion stylist and marketer, was married to Ben Mulroney, the son of late Canadian Prime Minister Brian Mulroney. Together, they were Toronto's premier power couple, a media-savvy duo whose polished lives were a permanent fixture in society pages.
Royal author Tina Brown, in her book The Palace Papers, described Jessica as a 'buzzed-up Toronto tastemaker'. Her surname alone carried immense cultural weight in Canada. Meghan, always attuned to image and opportunity, recognised in Jessica a working model for how to monetise visibility and turn personal life into a brand.
Jessica had expertly transformed every aspect of her life—from her lavish three-day wedding and parenting to fitness routines and travel—into promotional content. Her children featured in brand partnerships, and even gym sessions doubled as sponsored content. Meghan watched this closely. Physically similar, with matching long hair and aesthetic, the two women projected an image of intimate sisterhood on social media, sharing gushing tributes and curated images of their outings.
The Social Network: From Toronto to London's Elite
According to Brown, Meghan had a habit of cultivating relationships with influential women, absorbing their networks. While Jessica provided the Toronto playbook for blending marriage, branding, and proximity to power, another key figure helped unlock a global stage.
That was Markus Anderson, the Canadian-born global membership director of Soho House. Acting as her constant companion and guide, Anderson used his encyclopaedic address book to steer Meghan into elite circles she could not have accessed alone. Soho House became her 'glide path' into a mobile, global set defined by influence rather than aristocracy.
It was through these Soho House connections that Meghan is thought to have infiltrated London's high society, ultimately leading to her fateful meeting with Prince Harry. By the time their romance began, the Mulroneys were embedded in her inner circle. They attended the 2018 royal wedding, with their sons serving as page boys and their daughter as a flower girl. Jessica was also a guest at Meghan's controversial New York baby shower in 2019.
The Unravelling of a Strategic Alliance
The friendship, however, did not survive the pressures of Meghan's new royal life and a subsequent public scandal. In 2020, Jessica became embroiled in a dispute with Toronto influencer Sasha Exeter over accusations of bullying during the Black Lives Matter movement.
In an Instagram apology, Jessica wrote a line that publicly implicated Meghan, stating she had 'lived a very public and personal experience with my closest friend where race was front and centre'. After this, the pair were no longer seen together and faded from each other's social media. Earlier this year, Jessica and Ben announced their separation.
Meghan, meanwhile, completed a far more dramatic ascent. Tina Brown presents the Mulroney friendship not as mere coincidence but as part of a broader, deliberate strategy. Jessica Mulroney served as both a stepping stone and a launchpad, offering Meghan a crucial blueprint for turning a curated personal brand into unparalleled social and ultimately, royal, access.
