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Fay and Richwhite were also involved in a series of transactions between 1986 and 1993 involving their companies European Pacific Investments; Capital Markets; Fay, Richwhite; the Bank of New Zealand; Tranz Rail; and Telecom New Zealand, transactions in which they personally gained over half a billion dollars at the same time as their minority shareholders lost NZD$277 million.
In June 2007, Michael Fay and David Richwhite through one of the companies that they co-owned, Midavia Rail Investments, paid $20 million to the commission to settle insider trading proceedings relating to Tranz Rail.
Following Toll Holdings' investment in New Zealand's Tranz Rail in 2003, the Interislander was transferred to Toll Shipping.