Duchess Meghan, Princess Diana & Synchronicity: All Roads Lead To Chicago

  • Photo by Northwestern University

As I celebrate the birth of Archie Harrison Mountbatten-Windsor, I can’t help but have bittersweet feelings about Harry’s mom, the late Princess Diana, not being here to witness the birth of her youngest son’s first child. The first born to one of your children is typically considered a milestone event, not just for the parent, but also for the grandparents.

I keep reflecting back to how Prince Harry said in his engagement interview with Meghan in 2017 that he believed that if his mother was still alive, she and Meghan would be “thick as thieves.”

For those who don’t know what that term means:

Thick as thieves

“Two or more people very close or friendly; sharing secrets.” – Google Dictionary

Some of the synonyms for the term which Google gave me include:

Friendly, intimate, familiar, hand in glove; close to, devoted to, inseparable

I was born and raised in beautiful Chicago, and I am very proud of the fact that Princess Diana of Wales visited my beloved hometown in 1996, a year before she tragically died. I believe it was her last official visit to America.

Copyright rightful owner/People Magazine

I had recently moved to Los Angeles to attend school at that time, so I wasn’t in Chicago when Princess Diana made her greatly anticipated visit, but I heard all about it from my Chicago peeps and family.

In Chicago, Princess Diana’s visit was a very BIG deal.

The following excerpt is from an article which ran on the front page of the Chicago Tribune newspaper on June 5, 1996 under the front page headline “DI HARD 4: THE TAKING OF CHICAGO”

Here is an excerpt:

“Princess Di arrived in Chi and the town went gaga.

She worked her crowd like a pol and a potentate and usually sane, sensible people seemed to swoon.

The ones who touched Diana’s hand looked like they needed CPR. For those who got a brief word from the princess, it was hot diggity heart attack. Bring on the medics!

Even a mere sighting of the flirty royal made men weak at the knees.”

“I came for a hug,” declared Evanston’s David Studnitzer, 13. And when he told Diana so, she wrapped him in her arms.

“Cool,” David said.

It was hard to imagine that any other person besides a rock star could bring a 13-year-old boy outdoors to wait around for a long time, in a sprinkle, with his 15-year-old sister.” Chicago Tribune June 1996

I guess you could say Chicago was IN LOVE.

My older brother Stevie performed at a charity fundraiser gala which Princess Diana attended at Chicago’s legendary Field Museum. My brother is a well known local singer and musician in Chicago, and he was the lead vocalist for the orchestra for the event.

The legendary singer Tony Bennett was the headliner.

“Singer Tony Bennett serenaded Her Royal Highness, and the A-list guests included Deloris Jordan, Michael’s mother, who stopped by to present the princess with autographed Chicago Bulls souvenirs for Prince William and Prince Harry before running off to catch Game 1 of the NBA Finals.” Northwestern Magazine

Although my brother wasn’t fortunate enough to meet Princess Diana personally, being the lead vocalist on stage during a number of the orchestra’s songs, he had a great view of the gala’s front row star guest, and according to Stevie, Princess Diana looked more beautiful in person than she did in pictures.

So what does Princess Diana’s visit to Chicago in 1996 have to do with her future daughter in law the then Meghan Markle and Synchronicity?

It has this to do with it:

“Meghan Markle has a surprisingly sweet connection to her late mother-in-law Princess Diana.

Though Meghan grew up an ocean away from her future royal family, the bride-to-be almost crossed paths with Prince Harry‘s mom two decades before the couple first met. Almost 22 years ago, Diana visited Northwestern University — the very school Meghan attended from 1999 to 2003.

Though Meghan missed Diana by just three years, the royal made a huge impact on the school during her visit in early June of 1996. Diana spent five days visiting the university and the Chicago area where she met with students and stopped by a local hospital. The official reason for her visit was to raise money for the University’s Robert H. Lurie Cancer Center, according to North by Northwestern, since Diana was President of London’s Royal Marsden Hospital and its Cancer Fund at the time.” People Magazine – February 2019

Yes Princess Diana actually visited the same school her future daughter in law Meghan Markle would later attend…the only time I could find via my research that Princess Diana had ever visited a university in America.

*Meghan double majored in Theater and International Relations while at Northwestern U.

Princess Diana didn’t choose to visit Harvard, Yale, Cornell, or any of the other much more well known universities in America…

…Princess Diana chose to visit Northwestern U. Why?

In fact Northwestern University was reportedly the reason Princess Diana visited Chicago in the first place. She came to Chicago at the personal request and invitation of then Northwestern U’s president Henry Bienen.

Most of the time spent by Princess Diana in Chicago was at Northwestern University.

While there, Princess Diana even sat in on a seminar at Northwestern U.

“She sat in on a seminar at Northwestern University, toured a sculpture garden at Northwestern University, visited patients at Cook County Hospital and Northwestern Medical Center and headlined a benefit luncheon at the Drake Hotel. Then-Northwestern President Henry Bienen even held a reception for her at his home.” Shiakapos.com – August 2017

Think about that. Princess Diana walked the same campus as young Meghan, and possibly even sat in a classroom Meghan sat in while thousands of miles away from Britain.

Three years later Northwestern would be attended by the same girl her then 12 year old son Harry would grow up to fall in love with and marry.

Considering the US has hundreds of fine colleges and universities many which likely sent her invitations to visit, what are the odds that a year before her tragic death, Princess Diana would choose what I believe to be her one and only university to visit in America, a school that would three years later be her future American daughter in law’s chosen university?

The lovely Princess Diana even honored the school by wearing a stunning Versace dress in Northwestern U’s school color Purple at the Field Museum charity gala I referenced earlier.

“Diana stunned students and faculty when she stepped out at a fundraising gala wearing a gorgeous purple gown in the exact same shade as the university’s official color.

“I asked if she knew that purple was the color of Northwestern, because it could just simply be the royal color, and she just laughed,” former Northwestern president Henry Bienen told North by Northwestern in 2016. “I think she did it on purpose.”’ People Magazine

“The Princess of Wales was also the guest of honor at a black-tie fundraising gala at Chicago’s Field Museum of Natural History, where she wore a floor-length Versace gown — in Northwestern purple — and danced with TV host Phil Donahue.” Northwestern Magazine

Photo by Tim Graham/Getty Images

And if all this wasn’t serendipitous enough, months after her Chicago visit, Princess Diana was photographed wearing a Northwestern U sweatshirt while going to a gym in London, a sweatshirt she was gifted directly from the school thousands of miles away from the UK which her future American daughter-in-law Meghan would soon attend.

Princess Diana Northwestern University

Brendan Beirne/REX/Shutterstock

“It seemed Princess Diana indeed enjoyed her time there (in Chicago) as she was even spotted wearing a Northwestern University sweatshirt a few months after her visit.” IB Times

Tragically Princess Diana died the following year after that fateful visit to Chicago which means she was photographed wearing the Northwestern U sweatshirt in London mere months before her sudden and shocking death.

I can’t help but feel that Princess Diana’s visit to Chicago a year before she died was not a coincidence…plus I 100% agree with Einstein:

“Coincidence is God’s way of remaining anonymous.”Albert Einstein

Nor was it a mere coincidence that the only university in America that Princess Diana ever visited while on her multiple visits to the US over the years was the prestigious yet little known internationally university of the girl her then 12 year old little boy would grow up to fall in love with and marry years later.

Royal Wedding 2018

Nor was it a mere coincidence that Princess Diana would choose a stunning Versace dress to wear while in Chicago, the color of the dress purple, the same school color of Northwestern and a color which her future daughter in law would wear many times while attending the school over four years.

Nor was it a coincidence that Princess Di was snapped wearing a Northwestern U sweatshirt thousands of miles away from Chicago while in London mere months before her tragic death.

Princess Diana obviously felt a connection to Chicago and Northwestern U, though I doubt she knew why. I’m sure that we have all had those experiences where doing something odd feels so right even though we have no idea why it feels so right or why we’re doing it.

I believe that is a form of Synchronicity.

For those who don’t know the definition of Synchronicity:

“the simultaneous occurrence of events which appear significantly related but have no discernible causal connection.” Google Dictionary

I believe Serendipity also may be playing a role.

Interestingly when I went to find a definition for serendipity, I found this quote about the origin of the word:

“Serendipity does not come from Latin or Greek, but rather was created by a British nobleman in the mid 1700s from an ancient Persian fairy tale. The meaning of the word, good luck in finding valuable things unintentionally, refers to the fairy tale characters who were always making discoveries through chance. You can thank serendipity if you find a pencil at an empty desk just as you walk into an exam and realize that you forgot yours.” – Vocabulary.com

You can find a pencil at an empty desk that you needed right before taking an exam….or you could subconsciously connect with your 12 year old youngest son’s future soul mate’s university..

I doubt very much that Princess Diana knew the relevance that Chicago’s prestigious Northwestern University would have not only for her little boy, but for the millions around the world who are now so in love with Duchess Meghan, just like her deceased mother in law was so loved, but I truly believe Diana FELT drawn to accept the invitation from Northwestern U’s president to travel thousands of miles to come to Chicago to visit a school I doubt most in the UK had ever heard of…

…and I believe Princess Diana FELT something significant during her 3 whirlwind days in Chicago….a feeling that I believe she carried back with her to London as evidenced by her wearing the Northwestern U sweatshirt, a feeling that she did not want to let go of mere months before she tragically died.

“I was surprised by what a huge impact she had in Chicago. When we toured the sculpture garden there were people three and four deep behind the ropes. It was like that wherever she went,” said Bienen, now president of the Poetry Foundation in Chicago and emeritus-president of Northwestern.” Shiakapos.com

It’s safe to say that Princess Diana swept the Windy City off its feet…and Chicago isn’t easily impressed.

“I love Chicago,” Diana said as she boarded a British Airways plane for her flight home. “It’s been wonderful.” Northwestern Magazine

As we all celebrate the birth of Archie Harrison, let us take comfort in the fact that although Harry’s mom isn’t here to share in this momentous and blessed event which is blessed not only for the Royal family but for the world, that there is a strong possibility that Princess Diana’s heart gave its blessing to Meghan as a wife for her youngest son almost 23 years ago.

Photo by Georges De Keerle/Getty Images

“Only do what your heart tells you.” Princess Diana

This was likely done by Princess Diana following her heart to Chicago to be in the same location, environment, and space as Meghan would be in, and to walk the same grounds in the same city as her future daughter in law would walk a mere 3 years later.

And by wearing the gifted sweatshirt bearing the name of her future daughter in law’s school in London mere months before her life would tragically end.

Meghan very likely had that same sweatshirt.

Meghan said at the end of her and Harry’s anniversary interview in 2017 on the topic of Harry’s beloved mom, Diana not being there to celebrate their engagement and upcoming marriage with them:

“She’s still with us.”

I go back to the meaning of the phrase Harry used in that same interview:

“Thick as thieves.”

Thick as thieves meaning –

“Two or more people) very close or friendly; sharing secrets.” – Google Dictionary

Thick as thieves synonyms: Friendly, intimate, familiar, hand in glove; close to, devoted to, inseparable

Maybe, just maybe her future mother in law’s “thick as thieves” presence is something Meghan has felt in her life all along without really even knowing it.

Maybe Meghan felt Diana’s presence long before she met Harry, while she walked the campus of Northwestern where she reportedly volunteered for “The Glass Slipper Project” a non profit organization which helped disadvantaged young girls receive prom dresses so they could feel like Cinderella princesses at their proms.

I wrote about Meghan’s participation in this worthy non-profit while attending Northwestern U for Meghanpedia earlier this year. It was my very first contribution to this wonderful website.

Meghan Markle at Northwestern University & The Glass Slipper Project

Maybe God was remaining anonymous while guiding Princess Diana to the location her future daughter in law would attend school a year before Diana would be tragically killed in a car accident after being chased by photographers paid by the British Media, the same British Media which has been harassing Duchess Meghan for months with unfounded and/or false stories and accusations from suspect Kensington Palace sources all while pregnant with her first child.

Maybe Meghan has felt Princess Diana’s guiding presence in her life for years beginning with when she would three years after Diana’s momentous visit there, move to Chicago to attend Northwestern University.


Following is a brief yet poignant Chicago newscast from 2017 commemorating the 20th anniversary of Princess Diana’s death. It features some bittersweet footage of Princess Diana’s 1996 visit to Chicago:

Finally here is a video of Elton John performing his re-written version of his classic song “Candle in the Wind” at the funeral of Princess Diana in 1997.

It was the one and only time Elton has performed this special version of the song, and it is titled “Goodbye England’s Rose.”

RIP Princess Diana. Your spirit will never die and congratulations on your newest grandson. Peace.


Post navigation

One comment on “Duchess Meghan, Princess Diana & Synchronicity: All Roads Lead To Chicago

  1. Susan

    I thought I had read all your articles until I came across this one today. What a beautiful and well written article, as are all your articles. Indeed, God always remains anonymous and we never know why people cross our paths or why we choose to visit less known places… He is always guiding us and I honestly believe that the union between Duchess Meghan and Prince Harry are all in His plans. Thanks Meghanpedia and keep up the good work. The Duke and Duchess of Sussex needs our voices because they cannot always speak up to silence the lies being spoken about them.

Comments are closed.