Hillary Clinton—Whatever the legal process ultimately decides about her email practices, Clinton's digital obscurantism has proven to be a deeply, if not fundamentally, flawed political calculation. Her favorability numbers have been in free fall for months; her trustworthiness is now in the tank, perhaps inescapably; and she's only helped to revive the '90s narrative that the Clintons always have something to hide. Still insisting she owes nobody an apology, Clinton finally last week copped to the acknowledgment that hosting her State Department communications on her own private server "clearly wasn't the best choice." And then under mounting pressure, Clinton finally apologized Tuesday for using a private email server account while Secretary of State. "That was a mistake. I'm sorry," she told ABC News in an interview.
Jeb Bush—From the moment he entered the race, Jeb appeared so confident in his poll position, and so unthreatened by his track competition, that he figured he could just draft for a while. The self-described "joyful tortoise" quickly amassed a huge war chest, but seemed content to play $5 hands until the general election. He idly watched as Donald Trump smacked him left and right, returning little push back. Even after he reshuffled his senior leadership in early June, appointing GOP attack dog Danny Diaz as his campaign manager, Team Bush was still playing it safe.
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Jeff Miller, Rick Perry campaign manager—Whereas many of Perry's advisors headed for the hills following his disastrous performance ("oops") during the November 2011 CNBC Republican debate, Miller decided to go all. Having spent his career working for California GOPers, Miller decamped for the Lone Star state, where he led the effort to transform the tongue-tied Texas guv into an articulate, bespectacled technocrat— a politician of high-minded nuance. The only problem was, by the time Perry finally got his new Jean Lafont glasses, the GOP base had decided it was looking for someone a little rougher around the edges, and quite a bit less nuanced.
McKay Coppins—Political journalism collectively decided after the 2012 race to treat Trump's presidential flirtation as a slightly amusing, mostly annoying figment of his addled imagination. So many reporters (including this one) questioned when this perceived bluff would finally end—or what Trump was continuing to get out of the will-he-won't-he political dalliance. But no one so incisively laid bare these questions as Buzzfeed political reporter McKay Coppins last February, with his well-received, Hunter S. Thompsonesque exposition, "36 Hours On The Fake Campaign Trail With Donald Trump." It was the kind of story that any reporter (including this one) would have been thrilled to write, until, that is, Trump announced that he was running for president.
Trump—"You can't be imaginative or entrepreneurial if you've got too much structure," Trump wrote in his 1987 book, "Art of the Deal." "I prefer to come to work each day and see what develops." Given how little Trump thinks of pollsters, strategists and the conventions of political science, writ large, you'd have to credit his intuition. Despite the prevailing wisdom, post-2014, that the GOP elites had finally "crushed the tea party," and would now get back to the basics of producing mainstream, soccer-mom-appealing presidential candidates; Trump saw something so many others haven't. Turns out, the base was not ready to simply fall in line, and would rather line up behind just about anybody—even a twice-divorced, billionaire, Manhattanite, Democratic donor—who would speak their truth to the Republican establishment.
Bernie Sanders—You show me a 73-year-old socialist senator from Vermont, and I'll show you someone who probably couldn't half-fill an independent bookstore in Burlington. And yet, Sanders is shattering campaign rally attendance records from coast to coast. Why? Because he bet on the fact that the left was neither so hard-boiled utilitarian, nor so Clinton content, as the mainstream punditry believed. Now that Clinton is crashing with her server errors, Sanders finds himself leading in New Hampshire and gaining on the front-runner in Iowa. Sanders has spent 24 years in Washington (first in Congress, since 2007 in the Senate) but never has he held this much clout in the direction of his party.
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Will Pierce—Back in March, when Clinton was still basking in the glow of inevitability, Pierce, a 27-year-old former Obama campaign advance staffer, opened up a small office in Chicago to promote his shoestring effort to draft Vice President Joe Biden into the Democratic primary. Basing operations in Chicago seemed nonsensical enough—Biden is from Delaware—but, then, none of it made much sense at the time. The VP wasn't pondering a run, and no major Democrats seemed to think he would bring added value to the race. But following the emotional death of Biden's son, Beau, who had reportedly pushed his father to consider another run for president, Joe Biden's political future instantly took on a new light. And the once-fledgling Draft Biden group Pierce founded was suddenly a quite serious operation, enlisting major Democratic consultants and donors, while staffing up in key early election states.
Roger Stone—A former Nixon foot soldier who built his reputation as a GOP opposition researcher, Stone has lurked beneath the surface of national politics for decades now. Above the surface, Stone's done little of note in recent years, advising the no-shot New York gubernatorial campaigns of former procurer Kristin Davis (of Eliot Spitzer infamy) and gaffe-prone real estate developer Carl Paladino. A longtime Trump confidant, Stone was one of few people who was advising his political campaign at the start. Then last month, in the wake of Trump's bashing of Megyn Kelly, Stone split from the campaign, with both him and the candidate telling different break-up stories. But rather than fan the flames, Stone still capitalized on a week's worth of national publicity while dishing no dirt. His former boss didn't have time for Stone's soon-to-be-released book on the Clintons.
UDPATED: This story was updated to include news of Hillary Clinton's apology.