In 1999, Ezra Bray lived with O'Keefe's family whilst on an AFL scholarship to attend Essendon Keilor College.

[2] O'Keefe struggled to maintain his place in the Sydney side in his first few years at the club, but his form improved when he concentrated more on running and less on weight training.

He came equal second in the running for the Bob Skilton Medal, which is annually awarded to the Best and Fairest player at the Sydney Swans, to one of the three Co-Captains, Brett Kirk.

O'Keefe backed up his All-Australian form of 2006 with a memorable performance through the 07 season, once again finishing second in the votes for the Bob Skilton medal behind Brett Kirk who also was one of shining lights for the Swans.

After a strong start to the season, increased pressure was placed on O'Keefe following the suspension of troubled forward target Barry Hall.

Following the 2008 Grand Final, O'Keefe signalled his intentions to continue his career elsewhere, specifically in Victoria - his place of birth, after knocking back an initial three-year contract offer by the Swans.

O'Keefe did manage to play some impressive football however, particularly against Hawthorn at the SCG when he blanketed Luke Hodge while kicking four goals himself (he was awarded three Brownlow votes for his game).

He combined magnificently with the likes of Skilton Medal winner Josh Kennedy, Jarrad McVeigh, Kieren Jack, Lewis Jetta, Dan Hannebery and Craig Bird to become one of the best midfields in the competition.

In August 2014, O'Keefe quit the Swans due to limited opportunities and was hoping to be picked up by another club next year.

[7] After two years with Adelaide, O'Keefe replaced Torin Baker in December 2018 as coach of the Western Jets in the TAC Cup.