Billionaires Start 2026 With Huge Insider Buys

By Trey Thoelcke Updated Jan 9, 8:35AM EST · Published Jan 7, 8:45AM EST

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Under Armour Inc. (NYSE: UAA), W.R. Berkley Corp. (NYSE: WRB), and Gabelli Healthcare & WellnessRx Trust (NYSE: GRX) have just seen some huge insider purchases.
However, there were some other notable insider purchases as well.
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Billionaires Start 2026 With Huge Insider Buys — © Brandon Bell / Getty Images News via Getty Images

The so-called Warren Buffett of Canada and a prominent American billionaire investor and financial analyst started the year with huge insider purchases. Some of the most prominent buying that has been reported so far this year were from return trips to build stakes in Under Armour Inc. (NYSE: UAA), W.R. Berkley Corp. (NYSE: WRB), and Gabelli Healthcare & WellnessRx Trust (NYSE: GRX).

Though these were the most prominent insider purchases, there were a handful of other notable ones as well. Let’s take a quick look at these transactions.

Is Insider Buying Important?

What does insider buying tell us?

A well-known adage reminds us that corporate insiders and 10% owners really only buy shares of a company because they believe the stock price will rise and they want to profit from it. Thus, insider buying can be an encouraging signal for potential investors. This is especially so during times of market uncertainty, and even when markets are near all-time highs.

The fourth-quarter earnings-reporting season is yet to begin, so few insiders are prohibited from buying or selling shares. Below are some of the most notable insider purchases that were reported recently, starting with the largest and most prominent.

Under Armour

Buyer(s): 10% owner Fairfax Financial
Total shares: almost 13.2 million
Price per share: $4.81 to $5.19
Total cost: over $67.4 million

This buyer, led by billionaire V. Prem Watsa, sometimes called the Warren Buffett of Canada, also scooped up $70 million worth of shares prior to this purchase. The stake is now up to more than 41.9 million shares, and the investment helped boost the stock still suffering after the brand parted ways with spokesperson Steph Curry. Shares were last seen trading for more than the purchase price range above.

The stock is still more than 23% lower than six months ago. Given the Wall Street consensus target of $6.07, the analysts anticipate 8.2% upside in the next 12 months. However, only five of 26 analysts recommend buying shares. Guggenheim initiated coverage recently with a Buy rating with a $6 price target.

Watsa, founder and CEO of Fairfax, maintains a controlling interest in the company but reportedly is stepping back from some roles to plan for succession.

W.R. Berkley

Buyer(s): 10% owner Mitsui Sumitomo
Total shares: more than 672,700
Price per share: $68.92 to $71.15
Total cost: almost $47.2 million

Last spring, this buyer reached an agreement to acquire 15% of W.R. Berkley’s shares. Mitsui Sumitomo expects to complete its investment in this Connecticut-based insurance holding company during the first quarter of 2026. Its stake is up to more than 50.7 million shares, or over 13%.

The share price was last seen within the buyer’s latest purchase price range. Yet, the stock is 2.6% lower than six months ago because of recent volatility due to profit-taking. But note that shares are up 20.2% year over year, outperforming the S&P 500 in that time. Analysts are cautious, with only four out of 18 of them recommending buying shares. The mean price target of $73.06 is 3.2% higher than the current price but less than the recent all-time high of $78.96.

Mitsui Sumitomo is a massive Japanese financial conglomerate. Note that it also recently acquired an 18% stake in MassMutual’s Barings.

Gabelli Healthcare & WellnessRx Trust

Buyer(s): 10% owner Mario Gabelli
Total shares: 1.8 million
Price per share: $10.00
Total cost: about $18.0 million

This purchase followed on a 100,000-share buy reported at the end of last month. Gabelli also acquired shares of Gabelli Dividend & Income Trust (NYSE: GDV) and Gabelli Equity Trust Inc. (NYSE: GAB) in December. Note that another beneficial owner also picked up some shares of Gabelli Healthcare & WellnessRx Trust earlier in the month.

Shares were last seen trading for less than the $10 purchase price. They have underperformed the S&P 500 in the past year but are 4.2% higher than 90 days ago.

In addition, Gabelli also boosted his stake in Florida-based electronic equipment and components maker LGL Group Inc. (NYSE: LGL) in late December.

And Other Insider Buying

SEE D JAN / Getty Images

These were not the only notable insider purchases of the past week. Here is a quick look at some others.

Stock	Buyer(s)	Shares	Price	Cost
Lesaka Technologies Inc. (NASDAQ: LSAK)	executive chair	1.8 M	$5.00	$9.0 M
Mission Produce Inc. (NASDAQ: AVO)	a 10% owner	almost 290,000	$11.48 to $11.64	over $3.3 M
Corpay Inc. (NYSE: CPAY)	a director	8,000	$314.98	over $2.5 M

Some smaller insider buying was reported at CME, Gitlab, Joby Aviation, SAIC, and Simon Property as well.

The Biggest IPO of the Year Prompts Huge Insider Buy

About the Author Trey Thoelcke →

Trey has been an editor and author at 24/7 Wall St. for more than a decade, where he has published thousands of articles analyzing corporate earnings, dividend stocks, short interest, insider buying, private equity, and market trends. His comprehensive coverage spans the full spectrum of financial markets, from blue-chip stalwarts to emerging growth companies.

Beyond 24/7 Wall St., Trey has created and edited financial content for Benzinga and AOL's BloggingStocks, contributing additional hundreds of articles to the investment community. He previously oversaw the 24/7 Climate Insights site, managing editorial operations and content strategy, and currently oversees and creates content for My Investing News.

Trey's editorial expertise extends across multiple publishing environments. He served as production editor at Dearborn Financial Publishing and development editor at Kaplan, where he helped shape financial education materials. Earlier in his career, he worked as a writer-producer at SVE. His freelance editing portfolio includes work for prestigious clients such as Sage Publications, Rand McNally, the Institute for Supply Management, the American Library Association, Eggplant Literary Productions, and Spiegel.

Outside of financial journalism, Trey writes fiction and has been an active member of the writing community for years, overseeing a long-running critique group and moderating workshop sessions at regional conventions. He lives with his family in an old house in the Midwest.