On Tuesday night, Kentucky’s greatest modern political tactician extended his historic 36-year electoral winning streak by capturing the Republican nomination for the U.S. Senate. But this fall, Mitch McConnell’s magical ride—winning two county-wide races in the Democratic stronghold of Louisville before transforming Blue Kentucky into a reddish hue of purple through five U.S. Senate election cycles—will come to an abrupt halt.

Yes, you read it here first—I’m picking the long-shot filly in the most important Kentucky political horse race in a generation: On November 4, 2014, Alison Lundergan Grimes will be elected Kentucky’s next U.S. senator.

Dismiss me at your risk as a biased handicapper: While this recovering politician is an unapologetic Democrat, I’ve long held a deep, begrudging respect for McConnell’s unprecedented dominance of my home state’s politics. And just last April, after a Democratic-insider-led putsch helped nudge actress Ashley Judd out of a McConnell challenge, I suggested that the rising star Grimes would be foolish to take on our senior senator—whose unrelentingly brutal campaigns had helped end the political careers of four of his five Senate opponents.

But Grimes’ brand of chutzpah and moxie proved prescient. And as the general election campaign launches Wednesday, the young secretary of state is ideally situated to pull off what had long been considered a highly improbable victory.

One reason that I’m so early to declare victory is that, for a relative political newcomer, Grimes has been running a steadfastly solid campaign. Her slingshot cash collection has maintained stride with fundraising’s Goliath, even besting McConnell’s impressive haul in the most recent quarter. Grimes has grown, moreover, as a dynamic and disciplined candidate, benefitting greatly from the tutelage of two of the nation’s top political consultants, media maestro Mark Putnam and polling wizard Mark Mellman.

Certainly, Grimes has frustrated local wags by dodging tough questioning; but she’s wise to starve the 24/7 political attack-and-distort beast, a lesson in restraint that McConnell has expertly modeled for decades. And while she’s angered liberals with her pro-coal mining rhetoric (she most recently decried the coal divestment movement emergent on college campuses), there are scant few lefties who won’t relish the opportunity to replace President Obama’s chief antagonist with a loud female voice for passionate, progressive positions on the minimum wage, reproductive rights, equal pay for equal work, and anti-discrimination for LGBTs.

The $50 million question, of course, is how Grimes will hold up under the expected record-setting attack ad onslaught that the McConnell campaign and their barely uncoordinated SuperPACs will unleash in the coming weeks…or perhaps over the next few hours. Like her role model, Hillary Clinton, this lady is a champ: equipped with a dogged toughness and a willingness to take—and exchange—punches with the political heavyweights.

Even more promising, all of Mitch’s early jabs have missed their target. McConnell’s well-honed brand of seek-and-destroy politics is finding slippery footing in a fight against a much younger woman: Early efforts to paint Grimes as an “empty dress” and an “Obama girl” were met with bipartisan outrage from a sexism-sensitive chattering class.

In fact, to date, most all of Team Mitch’s efforts have been uncharacteristically underwhelming. Kentucky’s champion campaigner hasn’t exactly ventured into Todd Akin or Christine O’Donnell territory, but with mistake after misstep, the McConnell machine has been sputtering under a paucity of cylinders, earning exasperated criticism for awkward rifle-lifting photo-ops, over-reacting press blockades, and—heaven forbid in our hoops-addicted Commonwealth—Duke basketball-celebrating campaign ads.

I’ve joked that this unexpected incompetence was a sign that McConnell was pulling a Bulworth and trying to throw the election. But in sober reality, while Mitch’s past campaigns have been managed by top professionals—many with deep personal loyalties to the Minority Leader—his 2014 bid is being run by a newcomer to top-tier politics, whose heart might not really be in the race.

The decision to hire Ron and Rand Paul confidante and family member Jesse Benton as Team Mitch’s campaign manager was greeted initially as a bold strategic move to blunt Tea Party primary opposition. But after a recording surfaced of Benton stating that he was “holding my nose” while working for the establishment icon—and then after McConnell’s refusal to fire or even discipline him for insubordination—it seemed as if the senior senator was being held hostage by insurgent forces that lack the professionalism and experience to win the most highly watched, and likely the most expensive, race in the country. And even though the primary is finally in the books, it’s unlikely that McConnell will incur the Wrath of Tea—or more significantly, the ire of his uncomfortable ally, Rand Paul—by pushing Benton to the curb.

Indeed, with polls showing the general election matchup as a dead heat, the Minority Leader’s salvation must come from the 35 or so percent of GOP primary voters who shunned Mitch for businessman and Tea Party favorite Matt Bevin. His advocates passionately argue that ultra-conservatives will obviously choose the mere-conservative, instead of the fellow-Democratic-traveler of the most unpopular president in modern Kentucky history.

But I think it’s a mistake to characterize anti-Mitch Republicans as an ideological force. Bevin captured more than a third of the primary vote despite being dramatically outspent, despite failing to distinguish himself from McConnell on any substantive policy matter, and despite suffering a near complete campaign implosion due to self-inflicted mini-scandals: from exaggerating his affiliation to MIT, to being exposed as a pro-TARP bailout letter signatory, to worst of all, getting caught lying about knowingly attending a cockfighting rally.

Much of the explanation is personal—the reserved, sometimes prickly politico has never been well-liked. But Mitch’s true vulnerability can be found in the one strain of Kentucky politics that’s even more powerful than our socially conservative world view:

We hate Washington.

Kentuckians have long held a visceral resentment toward any outsider elite, be they meddling D.C. politicians or snooty Duke basketball players. It’s a cultural phenomenon so deep and toxic that it effectively bound Kentucky to the Confederate cause after the Civil War ended, and it helps explain why so many Bluegrass State voters oppose “big government” programs like Obamacare that have proven wildly successful in our poor state.

Rand Paul’s rocketing career trajectory is Exhibit A of this pervasive mindset. Paul’s secret among Commonwealth voters is not his libertarian dogma, but rather his ability to tap cunningly into the state’s aversion to elitist power in both parties. Indeed, in 2010, he launched from nowhere to the heights of the national political scene by handily defeating his opponent by successfully tarring him as the hand-picked candidate of the leader of the GOP establishment: Mitch McConnell.

And there’s the rub: When it comes to our deeply unpopular, polarized and paralyzed system of American government—when national polls show congressional approval lower than that of cockroaches and Brussels sprouts—Mitch McConnell is to many swing Kentucky voters the very symbol of everything that’s wrong with politics. And that’s why on Election Day, the power and the insider status that Mitch McConnell has painstakingly accrued over his long and extraordinarily successful political career will prove to be his ultimate undoing.