Pershing Square Holdings has agreed to invest up to $1bn in Howard Hughes Holdings to support its acquisition of specialty insurer Vantage Group Holdings, in a transaction valuing the business at approximately $2.1bn, according to a report by Bloomberg. The investment will be made through the purchase of non-voting preferred shares issued by Howard Hughes.

The acquisition will reportedly be financed through a combination of cash on hand and Pershing Square’s stock subscription. Pershing Square is the company’s largest shareholder, with founder Bill Ackman pursuing a strategy to reposition Howard Hughes from a real estate-focussed business into a diversified holding company with stakes in public and private companies.

As part of the transaction, Pershing Square intends to manage Vantage’s roughly $2.8bn investment portfolio at no cost, with plans to gradually increase its allocation to equities. As of the end of September, around 90% of Vantage’s invested assets were held in fixed income, according to company materials.

Founded in 2020 with $1bn in equity capital from Carlyle and Hellman & Friedman, Vantage generated approximately $1.2bn in net written premiums in the 12 months to September, split between specialty insurance and reinsurance. Ackman described the deal as a milestone in Howard Hughes’ transformation, with the transaction expected to complete in the second quarter of 2026.