Meghan Markle‘s close friendship with Canadian socialite Jessica Mulroney was glossy, strategic, socially useful – and potentially led her to Prince Harry.
Their tumultuous relationship significance comes back into focus today as Jessica and her ex-husband, Ben Mulroney mark the 18th anniversary of their engagement.
The couple went on to become Toronto’s hottest couple, a media-savvy duo whose polished lifestyle provided Meghan with a front row seat to power, branding, and elite social access at a crucial moment in her ascent.
Meghan met Jessica, now 45, in 2011 in Toronto and quickly recognised her as both a tastemaker and a model for how to turn visibility into influence.
Jessica was described as a ‘buzzed-up Toronto tastemaker’ by royal author Tina Brown in her book Palace Papers, and being the wife of Ben, son of the late Canadian Prime Minister Brian Mulroney, her surname alone carried enormous cultural weight in Canada.
Ben was already a known TV and radio host in Canada, and together the couple embodied a slick, aspirational brand of modern success.
Their engagement, announced in December 2008, kick-started a relationship that became a permanent fixture of Toronto society pages and glossy magazine spreads.
Toronto Life magazine ran a puff piece on them called ‘The Brandtastic Life of Ben and Jessica’, a title that neatly captured how thoroughly they had monetised their personal lives.
Jessica and Ben’s engagement, announced in December 2008, kick-started a relationship that became a permanent fixture of Toronto society pages and glossy magazine spreads
Meghan, who had always been attentive to image and opportunity, watched the monetising of Jessica and Ben Mulroney’s marriage closely
Jessica, a fashion stylist and marketer, had turned everyday moments into promotional opportunities, from her wedding and parenting to fitness routines and travel.
Her three-day nuptials became a national talking point, her children featured in brand partnerships, and even her gym sessions doubled as sponsored content.
Everything in Jessica’s world, Palace Papers notes, was carefully labelled, tagged and shared.
Meghan, who had always been attentive to image and opportunity, watched closely.
Physically, the two women could have passed for sisters, with similar colouring, long hair and an almost identical aesthetic.
On social media, they projected intimacy and ease, posting gushing tributes and endless images of shared trips, matching ripped jeans and carefully curated outings.
According to Ms Brown, Meghan had a long-established habit of flattering fashionable and influential women while absorbing their networks.
There was Misha Nonoo, the British-Bahraini fashion designer with international connections, Serena Williams entered Meghan’s orbit after a 2010 Super Bowl party, followed later by actress Priyanka Chopra, whom she befriended at a 2016 Elle dinner.
Jessica, a fashion stylist and marketer, had turned everyday moments into promotional opportunities, from her wedding and parenting to fitness routines and travel
Physically, the two women could have passed for sisters, with similar colouring, long hair and an almost identical aesthetic
Soon enough came Oprah Winfrey, described in Palace Papers as Meghan’s ‘ultimate ace-in-the-hole’.
At the same time, childhood friends such as Ninaki Priddy quietly fell away, as did her first husband Trevor Engelson.
Jessica stood out because her success was not just personal but structural. She had married into political and media power, and that alliance amplified her commercial reach.
It ‘could not have escaped’ Meghan, the book suggests, that a crucial factor in Jessica’s leverage was her famous, well-connected husband.
Jessica offered a working blueprint for how marriage, branding and proximity to power could combine.
But while Jessica provided the Toronto playbook, another figure helped unlock a far larger world.
That was Markus Anderson, the Canadian-born global membership director of Soho House.
With his encyclopaedic address book and instinct for social chemistry, Markus became Meghan’s constant companion and guide.
It was Markus who helped Meghan infiltrate London’s high society which is thought to be how Meghan ended up meeting Prince Harry
Jessica Mulroney attended Meghan Markle’s highly criticised baby shower in New York in 2019
As Meghan’s plus-one, he functioned like a walking dating and networking app, steering her into rooms she could not have accessed alone.
Without Markus’s Soho House connections, Ms Brown argues, it is unlikely Meghan would have penetrated London’s elite circles.
Soho House became her ‘glide path’ into a newly mobile global set defined by branding, influence and image.
Its members were brand consultants, marketing gurus, creative directors and tech evangelists rather than titled aristocrats.
A group of elite members were ‘curated’, rather than invited, by boards into the exclusive social circle.
For several years, usually with Markus in tow, its outposts dictated the direction of Meghan’s travel and social life.
The club’s aesthetic and ambition mirrored her own.
It was Markus who helped Meghan infiltrate London’s high society which is thought to be how Meghan ended up meeting Prince Harry.
By the time Meghan started dating Harry, the Mulroneys were firmly embedded in her inner circle.
Ben and Jessica attended the royal wedding in 2018, with their sons Brian and John serving as page boys and daughter Ivy as one of Meghan’s flower girls
Jessica became embroiled in a public dispute with Toronto influencer Sasha Exeter (pictured) over accusations of bullying during the Black Lives Matter movement
Ben and Jessica attended the royal wedding in 2018, with their sons Brian and John serving as page boys and daughter Ivy as one of Meghan’s flower girls.
Jessica was also among the select guests at Meghan’s lavish New York baby shower.
Yet the friendship did not survive the next chapter.
In 2020, Jessica became embroiled in a public dispute with Toronto influencer Sasha Exeter over accusations of bullying during the Black Lives Matter movement.
Sasha posted a video to Instagram asking fellow influencer to use their platform to support the Black Lives Matter movement. Even though JM was not named, she took Sasha’s message personally and went on an online tirade against Sasha.
Jessica did apologise but then was reported to have threatened legal action, which worsened the backlash.
The apology was made in an Instagram comment. One line of that apology read: ‘As I told you privately, I have lived a very public and personal experience with my closest friend where race was front and centre. It was deeply educational. I learned a lot from that.’
After implicating Meghan in her drama, the pair were no longer seen together, and they gradually disappeared from each other’s social media.
As it stands today, they have not been publicly linked for years and earlier this year, Jessica and Ben announced their split.
Meghan, meanwhile, completed a far more dramatic ascent.
Jessica Mulroney was a stepping stone and a launchpad and Ms Brown presents the friendship not as coincidence but as part of a broader, deliberate strategy.
