O’Toole? Ambrose? MacKay? Who will lead the Conservative Party of Canada

My drinking compadres could best be described as the millennial generation of hardcore Conservative supporters. And by hardcore, I mean they volunteer for campaigns–municipal, provincial or federal, wherever a hopeful they like may be–engaging in the thankless campaign drudgery of door-knocking and pamphleting, sometimes for days on end.

The more experienced among them even contribute to strategy, and for their efforts are often rewarded with work with victorious MPs. Others in these tight-knit circles that exist among all parties, also end up in the bureaucracy or at NGOs in the Ottawa beltway’s revolving door of organized politics, PR and public service gigs.

All of us had witnessed U.S. President Donald Trump’s election victory the previous November, and argued how Mr. Wonderful’s similar bombast might have played in his favour. On that subject, we could agree that O’Leary’s no-nonsense, direct manner with the media was his strongest quality.

Take for example the answer to a question about his French speaking ability, early on in Conservative leadership campaign: “I speak the language of jobs”, was peak O’Leary and a beautiful response worth pounding away on. Jobs. Economy. Jobs. Economy.

But in the end, O’Leary loathed the grind of on-the-ground politicking and despite a decent chance of victory, he pulled the plug and threw his chips in with a loser.

Insofar as political stratagem, it’s the kind of choice that separates an O’Leary from a Trump. Trump would never leave this sort of thing to chance and plays to win, while Mr. Wonderful gambled that a third of his supporters would vault Maxime Bernier to a first-ballot victory.

But in the field of 12 remaining candidates that included now-viable successors to Scheer–Erin O’Toole and Lisa Raitt–thirteen rounds later, Scheer squeaked out the win and the rest was history.

Not withstanding searing bouts of rhetoric from stalwart front benchers like Pierre Poilievre or Michelle Rempel, federal Conservatives remained stuck behind a simpatico leadership approach that stretched through the last election.

Even as Prime Minister Justin Trudeau’s antics, scandals and world-stage gaffes piled up, including Time Magazine revelations of avid blackface enthusiasm through our PM’s 20s–during an increasingly bitter election, no less–Scheer could never quite convert that into his advantage.

And Scheer’s leadership strategy never really diverged from this idea he could win by being a regular Joe – easy to be around and in other words not the millionaire playboy that the country’s 2015 choice for PM was turning out to be.

This failed programme was ultimately compounded by Scheer’s inability to square his personal religious views in a manner that the wider public could trust, on protecting gay, lesbian and trans rights and the incredibly polarizing issue of abortion.

By the time Scheer got around to showing any gumption on this subject–the memorable “is being gay a sin” exchange–he was scrumming with reporters after surviving a losing election post-mortem revolt at the party’s national caucus.

This time around, Conservatives need to find a winner. It seems a no-brainer, but this winner, wherever he/she/they may be, needs to be the sort who prevails in more than a leadership race or internal review.

This leader has to be the type of person where winning courses through their veins and maybe require an outsider with more zest for the glad-handing politics’ of the rubber chicken circuit than Mr. Wonderful had.

TRIGGER WARNING: During his Coach’s Corner prime, Don Cherry would have brought the perfect sort of everyman, energy required for such work –a Ralph Klein on blades – if only the leadership came å la sidekick Ron Maclean, playing Grapes’ foil of course.

Back in a post “you people” matrix, outsiders like Alberta energy tycoon Brett Wilson–another Dragon’s Den alumnus–as well as behavioural psychologist Jordan Peterson, have been bandied about social media as great replacements.

But if yardstick be real-world experience, paired with an ability to communicate effectively with a wider public, either are credible options especially given that Trudeau’s relative inexperience outside of politics was often compared to Scheer’s own career-politics trajectory, outside of briefly flogging insurance.

Back on the inside, former Conservative MPs who earned their stripes in previous Stephen Harper governments–former cabinet ministers Peter MacKay and Rona Ambrose–remain potential and formidable contenders if they choose to throw in their hats.

While MacKay has not ruled it out, Ambrose has indicated she’s not interested. Nevertheless, it’s early days with plenty of time to convince Ambrose she’s the perfect counterpoint to Trudeau.

Unlike MacKay’s Laurentien elite provenance, Ambrose’s Albertan roots would provide the West strong representation in Parliament and “because it’s 2015”, Conservatives could walk Trudeau’s often empty, gender talk.

What MacKay has going for him is a deeper cabinet resume, having served as attorney general, foreign affairs and national defence minister in former Harper cabinets. In terms of pure political calculations, the West is already solidly blue while MacKay’s corner of the country could use his ability to attract Maritimes voters back into the Conservative fold.

At the moment, all comers would be considered in the context of taking on a Trudeau-led Liberal Party in the next federal election. And if Trudeau’s insatiable appetite for attention, or another SNC-Lavalin level scandal emerges, from which there are no reasonable escapes; the caucus could oust their golden boy and all bets are off.

To date there have been no official announcements, but MacKay is said to be in preparations and O’Toole, a former Royal Canadian Air Force navigator and minister of Veterans Affairs, reportedly told “high-profile” Conservatives at a Friday Christmas party of his intentions to run.