Craig Darling, a director and 10% owner of Orion180 Insurance Group Inc. (NASDAQ:OIG), filed a Form 4 on October 26, 2026, disclosing eight open-market purchases of Class A Common Stock made between September 18 and October 6, 2026, all held indirectly through Darling Strategic Investments LLC.

Key Highlights

  • Eight purchases disclosed: Craig Darling acquired a total of 10,990 shares of Class A Common Stock across eight transactions dated September 18 through October 6, 2026.
  • Price range: Purchase prices ranged from $8.92 per share to $11.72 per share across the reported transactions.
  • Indirect ownership: All shares are held by Darling Strategic Investments LLC, of which Craig Darling is the manager with voting and investment power over the shares.
  • Resulting ownership: Following all reported transactions, beneficial ownership stands at 5,714,090 shares of Class A Common Stock, held indirectly.
  • Transaction codes: All eight transactions were coded "P" (open-market purchase) with shares acquired (A).
  • Reporting persons: The filing is signed by both Craig Darling individually and Darling Strategic Investments LLC, by Craig Darling as Manager.

Craig Darling's Series of Class A Share Purchases at Orion180 Insurance Group

According to the filing, Craig Darling reported eight separate open-market purchases of Class A Common Stock in Orion180 Insurance Group Inc. between September 18 and October 6, 2026. The earliest transaction on September 18, 2026, involved 100 shares acquired at $11.72 per share, bringing indirect beneficial ownership at that point to 5,703,200 shares.

Subsequent purchases occurred on September 21, 22, 23, and October 6, 2026, according to the filing. On September 21, two separate transactions added 500 shares each at prices of $11.68 and $11.56. On September 22, three transactions were reported: 1,000 shares at $11.11, 990 shares at $10.68, and 5,000 shares at $10.65. On September 23, 1,900 shares were acquired at $10.08. The final reported purchase, on October 6, 2026, consisted of 1,000 shares at $8.92 per share, bringing total indirect beneficial ownership to 5,714,090 shares.

The filing states that all securities reported are held by Darling Strategic Investments LLC. According to the explanation of responses, "Craig Darling is the manager of Darling Strategic Investments LLC and in such capacity has voting and investment power with respect to the shares held by Darling Strategic Investments LLC." Darling is identified in the filing as both a director and a 10% owner of the issuer. No derivative securities were reported in Table II of the filing.

What Was Disclosed

Craig Darling, director and 10% owner of Orion180 Insurance Group Inc. (NASDAQ:OIG), disclosed eight open-market purchases of Class A Common Stock totaling 10,990 shares between September 18 and October 6, 2026, all held indirectly through Darling Strategic Investments LLC, resulting in beneficial ownership of 5,714,090 shares.