Let me start 2018 with a confession: I may have been wrong about Jagmeet Singh.

I've been bullish on Singh for much of the last year, posting my first optimistic Loonie Politics column on the man back in January of 2017, before he was even a formal candidate for his party's leadership.

At the time, my thinking was relatively straightforward: Singh seemed cooler than Trudeau, more left-wing than Trudeau, less embarrassing than Trudeau, and — thanks to his superficial exoticism — more attractive to modern progressive voters and their preoccupation with demonstrating tolerance.

365 days, several dismal polls, and six disastrous by-elections later, it may be time to revise my thesis.  Even after the obligatory caveats that it's "still early," and Singh still has 21 months to close the deal, all present indicators point towards an NDP stuck in solid third place at best, and the brink of 1990s-style marginalization at worst.

What went wrong?

The thing about retail politics is that voters can easily interpret a politician's supposed talents as flaws, and his supposed flaws as virtues.  A failure to appreciate this was basically the story of Conservative attitudes towards Justin Trudeau.  The party and its supporters perceived Trudeau as an unqualified intellectual lightweight — which he was, objectively — and ran a campaign of teasing and derision.  But they failed to appreciate how, when viewed from more forgiving eyes, Trudeau's inexperience and naïveté could also come off as fresh, untainted, and upbeat — especially in the context of two dour, cynical opponents.

Singh's rise could prove the reverse phenomena: a politician whose seeming talents have blinded his supporters to the possibility others may interpret these as his worst deficiencies.

Is anyone really clamouring for a prime minister to Trudeau's left, for instance?  Unlike in America, where "single payer healthcare" has become a popular rallying cry for the further-left, there's no obvious policy way for Singh to contrast with Trudeau ideologically.  Trudeau is already quite far to the left on fiscal issues — indeed, a leading piece of conventional wisdom is that Thomas Mulcair did himself a disservice by advocating Ottawa spend within its means.  For a time, it seemed Singh could possibly get some traction out of advocating "no to everything" on the natural resource front, but championing this cause would require aggressively undermining the pro-pipeline NDP government of Alberta — itself facing an uphill battle for reelection — and perhaps soon the NDP government of British Columbia as well, who have been steadily lessening the flamboyance of their own opposition to various high-profile energy projects.

That leaves personality.  Ideology, after all, is as much about disposition as agenda these days, yet Singh bears no resemblance to the cranky Bernie Sanders or Jeremy Corbyn whom Canadian leftists have long fetishized.  Rather than affect a tone of populist, righteous anger, Singh has opted for a Kumbaya mantra of "love and courage" that's little different from Trudeau's own endless roster of maudlin slogans.

Singh's personal style also appears increasingly dated and immature in a way Trudeau, for all his silliness, never did.  The prime minister has an awkwardness about him that can come off as charming, and the ways in which he is obviously a lesser man than his father makes him attractively vulnerable.  The deliberate effort to market him as dorky, with his Star Wars socks and tweets about video games reflects awareness of this.

Singh, by contrast, is a 38-year-old still obsessed with being cool. He overdresses, has obviously expensive tastes, and talks in an obnoxious fratboy manner that begins to grate like sandpaper after the fifth consecutive Instagram story of him hooting at the camera with his arms around his boys.  Speaking as a 33-year-old who recently shaved his mustache in a pique of self-consciousness, the hipster aesthetic Singh embodies reflects an era fast ending, with a shrinking appeal even among its most stereotypical adherents.  It's particularly worth questioning how a man with this much bro-ish swagger hopes to peel young, female voters from the Liberals — one of the most critical pillars of Trudeau's coalition.

Singh's ethnicity is the cloudiest variable.  That Quebec is too racist to vote for him seems a relatively mainstream conclusion, albeit masked by euphemisms about "overt religiosity."  Yet Singh may paradoxically also find himself hampered by an inability to win over left-wing Anglo Canadians who are theoretically most open to electing a nonwhite prime minister.

Barack Obama was as popular as he was because he embodied a compelling American story.  His biracial status, foreign father, and "funny name" congealed into a biography of a man who was an almost perfect synthesis of America's history of race and multiculturalism.  In the eyes of white, liberal America, there was a redemptive symbolism inherent in electing him.  Singh, by contrast, comes off a much more narrow figure.  Sikh culture and politics appears to be the defining interest of his life, and the weird evasiveness he displayed in that infamous interview about Air India demonstrated an inclination to find nuance in what to most Canadians was not a particularly complicated tragedy.  There is a fine line between being the candidate of "diversity" and the candidate of one particular demographic.  The former is compelling and sympathetic, the latter is simply alienating.

I still think it's possible Singh's defining qualities could be aggressively reinterpreted by the press and progressive voters sometime before 2019, just as the dismissiveness that greeted Justin Trudeau's ascension as Liberal boss faded dramatically as 2015 drew closer.  The Prime Minister's numbers will probably have to undergo a dramatic, unforeseen cratering for that to happen, however.  Only then will progressive voters be desperate enough to find hope where they currently see little.

Written by J.J. McCullough