After the Liberal Party's defeat at the 2002 election, Olexander was promoted to the shadow ministry, taking on the portfolios of Youth, Arts and Consumer Affairs in December 2002.
[1] In June 2006, Olexander was reported to have drafted a Private Member's Bill that would allow gay civil unions in Victoria.
[6] He attracted some attention in late 2004 for advocating for greater funding for gambling support groups and his criticism of the government's backdown on their election promise to extend the Epping railway line to South Morang.
[7] On 7 January 2009, Olexander appeared before the Melbourne Magistrates' Court, accused of driving on the CityLink tollway three times without a pass.
Magistrate Sharon Cure ordered Olexander pay a $100 fine on each of the three counts of using an unregistered vehicle on a tollway plus $40 in court costs.
[12] On 29 November Olexander was expelled from the Liberal party, although some, including Ted Baillieu, a potential challenger to Doyle voted against the expulsion.
The Age commented on the expulsion that "Mr Olexander must have known it would end like this... [he] should have accepted his party's verdict with grace, acknowledging it as both inevitable and just.