Kevin O’Leary is a businessman who has been touted Trump-like on his approach to politics. Disclosure: this is not an endorsement of Kevin O’Leary and is in no way a promotion of his ideology.
Kevin O’Leary initially strikes to me as a Trumpesque candidate who could possibly be running on the slogan “make Canada great again”, but after my examination of his political positions, he would hardly resemble Trump outside his talking points, such as “I have great people working for me now. I surround myself with smart people. ” 
For instance, O’Leary’s political views on social issues, such as abortion, LGBT+ rights, regulation of cannabis, assisted suicide, etc is very liberal leaning, similar to the views of U.S. mainstream-to-progressive liberals.  O’Leary’s view on immigration is also very moderate, unlike. 
On economic policy, this is the area that O’Leary deviates from mainstream liberals.  O’Leary wants to eliminate the federal carbon tax and to adopt a free-trade policy (supportive of both NAFTA and TPP), a position that puts him slightly to the right of New Jersey Democratic Senator and 2020 presidential hopeful Cory Booker, (Booker supports Vouchers, O’Leary’s view on the issue is unknown; Booker supports environmental protection apparatus, O’Leary leans oppose).  O’Leary believes in a balanced budget (where Trudeau is anti-austerity as is Booker), foreign ownership of Canadian airlines, as well as deregulation of Canadian banking industry (a position Booker supports). 
Overall, based on his disclosed political views, O’Leary would find himself close to Cory Booker on the ideological spectrum, if not slightly to Booker’s right. O’Leary would be the standard-bearer of a fiscally centrist and socially liberal candidate, a view that most Conservative leadership voters share. On paper, O’Leary would generate less of a bombastic effort than Kellie Leitch, whose xenophobic and unapologetically tea party ideologies would turn off most Canadian voters, as O’Leary takes positions that Canadians actually take. You can read Leitch’s official positions on Leitch’s official website, but for the sake of saneness I decided against linking.
O’Leary’s campaign message–fiscal centrist and social liberal–would be an effective slogan to Conservative primary voters; after the primary, O’Leary would be free to move his position along the ideological spectrum, but his primary strategy would be a swing leftwards, as his economic policies are already on the neoliberal side of the Canadian spectrum.
O’Leary’s status as Conservative frontrunner guarantees another important view that many Canadians care about–Canada would not have a Trumpesque leader, like Leitch, to threaten the civil and political rights of all Canadians, regardless of race, sex, sexual orientation or national origin.
1. “Q&A: Kevin O’Leary on why he’s running for the Tory leadership.” Macleans.ca. MacLeans Magazine, 19 Jan. 2017. Web. 25 Jan. 2017.
2. Elliott, Josh. “Kevin O’Leary enters Conservative leadership race: ‘I’m in'” CTVNews. N.p., 18 Jan. 2017. Web. 25 Jan. 2017.
3. “Kevin O’Leary points toward the wrong path: Editorial | Toronto Star.” Thestar.com. The Toronto Star, 18 Jan. 2017. Web. 25 Jan. 2017.
4. Julie, Alyssa. “Kevin O’Leary promises to scrap the carbon tax if elected prime minister.” Global News. N.p., 21 Jan. 2017. Web. 25 Jan. 2017.
5. OnTheIssues.org. “Cory Booker on the Issues.” Cory Booker on the Issues. N.p., n.d. Web. 25 Jan. 2017.
6. Vandaelle, Ian. “Bank mergers, housing and marijuana: Kevin O’Leary on his leadership bid – Article.” BNN. Bell Media, 18 Jan. 2017. Web. 25 Jan. 2017.