Billionaires Start 2026 With Huge Insider Buys

24/7 Wall St. Key Points

  • 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.

By Trey Thoelcke Updated Published
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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?

insider buying
frender / iStock via Getty Images

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

 

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