Jennifer Gwynne on Selling College Ex-Boyfriend Elon Musk’s Photographs, Mementos at RR Auction

Sometimes, hanging on to an old box of your ex’s stuff can really pay off.

A stack of old photos, taken together, at home or with friends. A signed birthday card. A special necklace, given as a gift.

For most of us, hanging on to a box of memories after a breakup usually only leads to a bigger garage sale down the line. But for Elon Musk’s college sweetheart, a trove of mementos from the nineties became an unexpected windfall. 

“For many years in the back of my mind, I always thought I would sell my Elon Musk items from my college days,” Jennifer Gwynne, Musk’s ex-girlfriend, tells RR Auction. She just wasn’t sure when, where, or how. 

That changed when Gwynne read about a fellow UPenn alum selling two class assignments graded by Musk at an RR Auction sale. The pieces went for over $7,700 in December 2021. 

“Until I read that article, I didn’t know who I could trust to help me make the most of my very unique situation,” Gwynne recalls. She resolved to reach out and get RR Auction’s input.  

“I knew from their recent Steve Jobs, Apple computer, and Space Exploration auctions, that RR Auction had their finger on the pulse of the ‘tech-guru’ artifact market,” she says. “They understood what bidders were looking for and what they found exciting.”

Gwynne’s leap of faith paid off: Her items, including some 18 original photographs, fetched close to $200,000. She’ll use the funds to help send her stepson to college, she says. 

“We are always thrilled and honored when one of our auctions can impact the lives of our consignors, as this sale has done,” says Bobby Livingston, RR Auction’s executive vice president.

The majority of the lots consigned by Gwynne to the Fine Autograph and Artifacts auction were photos of the Tesla, Twitter, and SpaceX CEO during their college days at the University of Pennsylvania. A birthday card he sent to her sold for $16,643, a dorm room picture of Musk laying upside down with his feet up on a desk sold for $21,889, and a 14-karat gold necklace Musk gifted to her in 1994 sold for $51,008, the top-earning item. The necklace has a small green emerald charm that Gwynne says came from a mine Musk’s father, Errol Musk, owns in Africa. 

A 14-karat gold necklace with an emerald was given by Elon Musk to his college girlfriend, Jennifer Gwynne. It sold for $51,000 at auction.
A 14-karat gold necklace with an emerald was given by Elon Musk to his college girlfriend, Jennifer Gwynne. It sold for $51,000 at auction.

“I wore the necklace for a number of years on and off, but it’s mostly been in my jewelry box for the last 10 years (always reminding me of Elon, of course),” Gwynne tells RR Auction.

Together, the photographs and mementos tell the story of a young couple in love: goofing around together, traveling to visit each other, and being silly with friends and family. It’s a softer, unguarded side of Musk rarely seen now in the media. 

“I think these items are a snapshot of who Elon was just before he started to conquer the world,” Gwynne told PEOPLE Magazine in an exclusive interview, arranged by RR Auction preceding the sale. “The photos show his less serious side — his silly, come-play-with-me attitude which would pop up now and then.”

“His everyday quiet intensity was really what attracted me to him initially… I’m a sucker for tall, blonde, and nerdy,” she added. 

This photo of Elon Musk in college, consigned by his ex-girlfriend, sold for $21,889 at auction.
This photo of Elon Musk in college, consigned by his ex-girlfriend, sold for $21,889 at auction.

The sale was a sensation, drumming up interest from media outlets throughout the U.S. and the rest of the world. In addition to speaking to PEOPLE, Gwynne was featured in stories by CNN, Inside Edition, the Boston Globe, the Times UK, Bloomberg, the New York Post and others. 

“I felt supported and valued from day one in working with RR Auction. As a team, we took my never-before-seen before Elon Musk items to the public, and together we made a media splash and had some absolutely mind-boggling sales results,” Gwynne says.

The media frenzy brought in huge amounts of interest in the auction—including none other than Elon Musk himself. 

“On the morning of the auction, Elon changed his profile picture on his official Twitter account to be one of my pictures: Lot 91, the picture of him smiling ear-to-ear in a UPenn study hall wearing his favorite Judge Dredd t-shirt,” Gwynne recalls. “His virtual thumbs up sent all his fans (and I’m sure also his detractors) to my auction items.”

And in a recent twist that could make Elon Musk memorabilia (Muskorabilia?) even more valuable, the tech entrepreneur recently announced to paparazzi that he will no longer be signing any more autographs. 

“Elon Musk is one of the most successful entrepreneurs of the 21st century,” Livingston says. “There is very little Musk-related material that has come up for auction, and we will no doubt be seeing more soon with the success of this sale.”

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