Skyward Specialty & Reinhart’s Bet

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You know, the world of insurance isn’t generally considered a hotbed of excitement. It’s more often associated with small print, lengthy claim processes, and a general sense of impending doom (ironically, for a business dedicated to preventing it). But every now and then, something happens that makes you sit up and take notice. And recently, Reinhart Partners, a Wisconsin-based investment firm, decided to double down on Skyward Specialty Insurance Group. Not just a little double down, mind you. We’re talking an $38.6 million purchase of 803,217 shares, as reported in an SEC filing on February 10th, 2026. Which, in the grand scheme of things, is a considerable pile of money, even for those who routinely deal in such figures.

Skyward Specialty, for those unfamiliar, isn’t insuring your car or home. They specialize in commercial insurance – the kind businesses need for particularly tricky or complex risks. Think things like professional liability, excess liability, and all sorts of other policies with names that would make your average homeowner glaze over. They’re based in Houston, which, oddly enough, feels appropriate. Houston being, as it is, a city built on calculated risks.

What Does This Actually Mean?

So, why did Reinhart Partners decide to increase their stake? Well, the simple answer is they believe Skyward Specialty is a good investment. But it’s never quite that simple, is it? The purchase brings their holding to 3.7% of their 13F AUM as of December 31, 2025. AUM, for the uninitiated, stands for Assets Under Management. It’s a bit like a financial version of a hoarder’s collection – the more they have, the more impressive (and slightly worrying) it is.

As of February 10th, Skyward shares were trading at $45.49, which, interestingly, is down about 6.8% over the past year. Now, that might sound discouraging, but consider this: shares have still advanced 211% since the company went public in January 2023. That’s a compound annual growth rate of 44.5%. Which is…substantial. It’s the sort of number that makes you wonder if you should have invested in insurance companies all along.

However, the stock has been hovering near its 52-week low of $42.45, and the commercial insurance market has been experiencing a bit of a slump. And, adding a dash of intrigue, some company insiders have been selling off shares. Insider selling isn’t always a bad sign – sometimes people just need to buy a yacht – but it does give pause for thought.

The Bigger Picture

Reinhart Partners isn’t alone in seeing potential in Skyward. Their top holdings, as of the latest filing, include FCNCA ($167.04 million), SIMO ($145.85 million), YETI ($134.08 million), IDCC ($132.97 million), and ACLS ($127.73 million). A diverse portfolio, to say the least. But Skyward Specialty is clearly one they believe in.

The company itself generates revenue primarily through underwriting insurance policies and managing risk. It’s a complex business, involving actuarial tables, probability calculations, and a healthy dose of educated guesswork. And it’s a business that’s increasingly important in a world full of…well, everything.

Here’s a quick snapshot of Skyward Specialty’s financials:

Metric Value
Revenue (TTM) $1.34 billion
Net Income (TTM) $141.20 million
Market Capitalization $2.06 billion
Price (as of market close 2026-02-10) $45.49

So, what should investors do? Well, that’s always the million-dollar question, isn’t it? Perhaps, as some suggest, it’s worth taking a closer look at a list of the best insurance stocks of 2026. After all, in the unpredictable world of finance, a little diversification never hurt anyone. And, frankly, it’s always good to have a plan. Even if that plan involves hoping for the best and bracing for the worst.

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2026-02-13 02:13