Company: KG
Filing Date: 2025-03-24
Form Type: S-4/A
Source: 0001104659-25-027242
Chunk: 112

Company: Kestrel Group Ltd
Filing Date: 2025-03-24
Form: S-4/A
Chunk 112
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’s bye-laws.

#### Assistance
If you need assistance in completing your proxy card or have questions regarding the Maiden special meeting, please contact Innisfree M&A Incorporated, the proxy solicitation agent for Maiden, by telephone at (877) 750-0502 (toll-free from the U.S. and Canada) or +1 (412) 232-3651 (from other locations).

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TABLE OF CONTENTS

### THE TRANSACTION

### Background of the Transaction
The Maiden board and Maiden management regularly evaluate industry conditions and Maiden’s operations, financial performance and long-term strategic goals. As part of this ongoing evaluation, the Maiden board and Maiden management consider potential opportunities to enhance shareholder value through business combination transactions and other strategic alternatives. In particular, the Maiden board has been focused on the fact that Maiden did not presently have an active operating business.

More specifically, the Maiden board had identified the benefits to Maiden of transitioning from a balance sheet business toward a fee-based business model focused on insurance businesses, which could also enable it to selectively underwrite business to optimize shareholders’ returns. The Maiden board believed a fee-based model would enable Maiden to generate more predictable streams of income.

In early 2024, Maiden was evaluating the potential acquisition of one or more MGAs, that were fee-based businesses. The Maiden board recognized that multiple acquisitions would be required to achieve sufficient operating scale and, therefore, could increase the complexity and execution risk relative to a single larger transaction. In the course of exploring a potential acquisition of one or more MGAs as well as exploring other insurance-focused fee-based businesses, Barry Zyskind, Chairman of the Maiden board, advised Patrick Haveron, Chief Executive Officer and Chief Financial Officer of Maiden, that Kestrel, a company in which AmTrust is a minority investor, was considering opportunities to grow its business and could potentially be interested in a business combination transaction with Maiden. Mr. Haveron was familiar with Kestrel and its founders, Luke Ledbetter and Terry Ledbetter (the “Ledbetters”), as Terry Ledbetter had successfully founded, grown and sold a highly successful fronting company named State National Companies, Inc. (“State National”).

During a discussion with Mr. Zyskind and Adam Karkowsky, President of AmTrust, on March 6, 2024, Mr. Haveron expressed interest in exploring a possible business combination of Maiden and Kestrel that would provide Kestrel with selective underwriting capacity to grow