The 2005 premiership hero joined the Board of the Sydney Swans ahead of season 2020. Since retiring from football in 2009, Leo has forged a career in investments, working as a broker at Merrill Lynch before joining fund manager Fairview Equity Partners, where he has spent the past five years. He is recognised as a leading broker within the finance industry.

As a footballer, Leo played 237 games for the Swans and co-captained the side from 2006 to 2008. He will forever be remembered for his match-saving mark in the 2005 AFL Grand Final.