In September 2000 around the time of the announcement of the Allianz joint venture, Adler persuaded the HIH chief executive at the time, Ray Williams, to provide $10 million of HIH's money to allow him to invest and ostensibly make money for HIH. One of the investments Adler made, through a trust called Pacific Eagle Equities, was HIH shares at a time when the HIH share price was falling sharply. The investment was a poor one, as the price continued to fall. Adler resigned as a director of HIH in January 2001. He was subsequently charged, tried and jailed for two and a half years over breaches of his director's duties.