Negotiations over an 836,000-square-mile island may fall to a close friend of Elon Musk with experience in deal-making. Just not that kind of deal-making.
President-elect Donald J. Trump has tapped Ken Howery, a venture capitalist, to help broker a deal to buy Greenland.Credit…IBL/Shutterstock
Ken Howery, a reserved and discreet tech investor, has unexpectedly found himself at the center of two high-profile narratives tied to the incoming Trump administration.
One involves the ambitious pursuits of Elon Musk, a close friend and former collaborator from their days running PayPal 25 years ago.
The other concerns the expansionist vision of President-elect Donald J. Trump, who has expressed interest in acquiring Greenland, the world’s largest island.
As Mr. Trump’s nominee for ambassador to Denmark, Mr. Howery is poised to play a pivotal role in what the president envisions as a landmark real estate deal. The challenge, however, lies in Denmark’s firm stance that Greenland, an autonomous territory, is not for sale.
Whether he likes it or not, Mr. Howery, a globe-trotter known for his taste for adventure and elaborate party planning, is likely to find himself in the middle of a geopolitical tempest.
Mr. Trump has been explicit about his expectations for his new ambassador filling a once-sleepy post. When he announced Mr. Howery for the role, which requires Senate confirmation, he reiterated his designs on Greenland for the first time since winning the presidency.
“For purposes of National Security and Freedom throughout the World, the United States of America feels that the ownership and control of Greenland is an absolute necessity,” Mr. Trump wrote on Truth Social late last year. “Ken will do a wonderful job in representing the interests of the United States.”
Thanking Mr. Trump on X, Mr. Howery mentioned not just the U.S. Embassy in Copenhagen but also the U.S. Consulate in Nuuk, Greenland, saying he was eager to “deepen the bonds between our countries.”
On cue, Mr. Musk chimed in: “Congrats! Help America gain Greenland.”
Mr. Howery’s mission is an example of what awaits the crop of Silicon Valley donors who swarmed to Mr. Trump during the campaign and now intend to follow him into public office. While many are seasoned deal-makers, their private sector experience may only go so far in serving the unpredictable Mr. Trump.
Mr. Howery did not respond to requests for comment. In private conversations, friends say he holds traditional conservative views and is hardly a Trump die-hard. He is drawn to diplomatic roles not out of ideology but for the overseas experience, they said. He is expected to be in Washington this week, hosting a rooftop cocktail reception opening the inauguration weekend on Friday, according to a copy of the invitation.
Mr. Howery is, in fact, signing up for a second tour for Mr. Trump. He served as ambassador to Sweden for 16 months during Mr. Trump’s first term; a delayed Senate confirmation shortened his tenure.
Still, he received some practice in the art of explaining Mr. Trump to skeptics overseas. As Mr. Trump denigrated NATO, which Sweden was moving toward joining, Mr. Howery defended Mr. Trump as “unconventional” and he visited the Arctic, an important outpost for NATO’s defenses.
The U.S. ambassador to Sweden, Ken Howery, right, with the Air Force secretary Barbara Barrett and the Sweden defense minister Peter Hultqvist in 2020.Credit…IBL/Shutterstock
Persuading Denmark to part with Greenland may require Arctic diplomacy of a whole other level. Leaders in both Denmark and Greenland have repeatedly said they are not interested in a sale, and chortled at Mr. Trump’s approach to deal-making on social media.
“I think Ken Howery was an effective ambassador to Sweden several years back. I absolutely believe in the private-sector experience,” said Rufus Gifford, who served as President Barack Obama’s ambassador to Denmark and was a top fund-raising official on Vice President Kamala Harris’s presidential campaign.
“But I’d say this: If you’re entering into the political firestorm that would be Donald Trump’s stated desire to purchase Greenland, I don’t believe there’s very much on your résumé that can help you navigate that,” he said.
Mr. Howery’s résumé begins at Stanford University in the 1990s, where he showed an early interest in politics as an undergraduate editor in chief at the conservative Stanford Review. When he graduated in 1998, he connected quickly with Peter Thiel, The Stanford Review’s rabble-rousing founder, to execute the investor’s orders.
Mr. Howery and Mr. Thiel soon started PayPal, the online payment service, where they were later joined by Mr. Musk. The three became charter members of the “PayPal Mafia” that has grown to dominate Silicon Valley. Mr. Howery and Mr. Thiel, who are still very close, went on to start Founders Fund, one of the industry’s leading venture capital firms.
With blond hair and a youthful face, the 49-year-old Mr. Howery, who is known as Kenny by friends, has little of the abrasive swagger or edge of Mr. Thiel and Mr. Musk. Some close to him described him as more of a people-pleaser than a cutthroat corporate operator. Nearly all of Mr. Howery’s associates interviewed for this article spoke on the condition of anonymity so as not to damage their relationship with Mr. Howery, who typically shuns the spotlight.
Ken Howery is far from a wallflower. Known for his extravagant lifestyle and elaborate events, he has garnered attention for hosting high-profile celebrations. In November 2020, he marked his birthday with a grand party at a castle near Stockholm, an event that later gained notoriety when Elon Musk revealed he contracted Covid during the trip.
For Halloween 2022, Mr. Howery organized a lavish “Transylmania” party at a castle in Transylvania, Romania. The event, attended by billionaires including Peter Thiel, took seven months of planning, according to a social-media post by one of the organizers. Despite no longer holding his diplomatic role, Mr. Howery used his ambassadorial insignia on thank-you notes sent to the planners.
Unmarried and with a daredevil spirit, Mr. Howery embraces adventure, often to the concern of friends. Labeling himself an “explorer,” he has visited 99 countries, traveling extensively for surfing, kiteboarding, and storm-chasing. His pursuits include racing a Tesla Roadster in the Gumball 3000, competing in yacht races aboard his Gunboat 68 Tosca, learning free diving in Fiji, and training as a chef in Paris for three months, as documented in now-private social media posts.
Despite his adventurous lifestyle, Mr. Howery’s close ties to Elon Musk have significantly shaped his public image. Associates report that individuals seeking Musk’s attention, whether for notes or packages, are often directed to go through Mr. Howery. Job-seekers, too, have sent résumés to him for delivery to Musk.
In recent years, Musk has frequently stayed at Mr. Howery’s home in Austin, though Mr. Howery has mentioned that these visits have become less frequent.
Ken Howery has been a trusted adviser and ally as Elon Musk’s wealth and ventures have expanded. He played a key role in advising Musk on the purchase of Twitter and personally invested in several of Musk’s ventures, including Neuralink and xAI.
Despite his involvement, Mr. Howery prefers to keep his friendship with Musk understated. In a 2019 interview with a Swedish publication, he said, “I’m friends with Elon. I really don’t like to comment on my personal friendships in a public forum. But obviously an amazing person. Very inspirational.”
In recent years, Mr. Howery has become increasingly political alongside Musk, particularly during the Trump era. He attended the Republican National Convention as part of a group of tech leaders and was seen mingling at events with Donald Trump Jr. Additionally, Mr. Howery is a member of the Rockbridge Network, an influential collective of Republican donors, many with ties to Silicon Valley.
In September, he co-hosted a fundraising dinner in Austin for J.D. Vance, Donald Trump’s vice-presidential pick.
Elon Musk has been a close friend of Mr. Howery’s since the two helped run PayPal 25 years ago.Credit…Al Drago for The New York Times
When Mr. Musk decided to start a super PAC last spring, he asked other donors to pitch in first to help him to hide his involvement for as long as possible. In June 2024, Mr. Howery made some of the very first contributions, making four separate $250,000 contributions to cover the super PAC’s initial costs.
“He went out of his way to donate and be helpful when I was helping to raise money for President Trump at the start of Elon’s America PAC,” recalled Joe Lonsdale, a friend and fellow Republican donor.
After Mr. Trump’s victory, both Mr. Musk and Mr. Howery have reaped rewards. Mr. Howery has been a reliable presence at Mar-a-Lago since election night, and he accompanied Mr. Trump and Mr. Musk to the recent SpaceX launch in Boca Chica, Texas.
After his abbreviated tenure in Sweden, Mr. Howery began to strategize with friends about angling for a European encore. He bandied about several countries and ended up on one with half the population as his last Scandinavian one.
But he told friends that he was specifically enticed by Denmark in part because of the possible Greenland acquisition. The challenge of working on one of the most complicated real-estate transactions on behalf of a real-estate mogul is one that could bring Mr. Howery the sort of attention he prefers.
After all, even as Mr. Howery keeps a low profile, he has, in private conversations over the years, mused about running for office some day, possibly in his home state of Texas.
