On a sun-dappled summer day 10 years ago, a balding, slightly manic man threw open the door of the J. Crew Collection boutique on the corner of Madison Avenue at 79th Street and made a beeline for the first employee he spotted. “Hey, who are you?” he demanded of a college student—let’s call her Emma—re-folding the stack of cashmere sweaters she’d folded a hundred times that summer. “Um, Emma?” she replied. “Emma! We have Emma!” the man exclaimed, his Bronx accent reverberating through the almost empty store. She looked around. Who was “we”? “O.K., Emma, whaddya think—how are we doing with these sweaters?” It took a second to spot his cell-phone headset, and another to realize that Millard “Mickey” Drexler, her boss’s boss’s (boss’s boss’s) boss, was conferencing this impromptu recon session back to corporate. Only later would she learn that such calls were piped through the entire company HQ, via Drexler’s infamous intercom system. Emma wasn’t just talking to the C.E.O. of J. Crew. She was talking to all of J. Crew.

In corporate fashion, where decisions tend to be handed down like decrees, Mickey Drexler reveled in the scrum. For 14 years, he paced—and sometimes biked—the halls of J. Crew’s multi-story headquarters near Manhattan’s St. Mark’s Place, interrogating everybody he came across: salespeople, designers, the mail guy. Over fried artichokes at Morandi, or in the office, over sliced peaches he had flown in from California, he peppered business talk with colorful tales about, say, the submarine he once toured with the founder of Under Armour. When it was time to choose the cover of the next catalogue, he convened a room of employees and put it to a vote. Sure, everyone knew this was mostly an exercise—chances are, the creative whizzes would talk Mickey into the cover they’d picked from the get-go—but so what? Everyone was game. If you worked for Drexler, you did not merely pocket a paycheck. You wore, lived, breathed J. Crew. Quips a former employee, “We were a bunch of not-as-cute catalogue models.”

Here’s the thing about Kool-Aid drinkers: they work hard. Together with designer Jenna Lyons—his right hand and the brand’s creative engine throughout most of his tenure—Drexler built a team that breathed an unlikely second life into a mid-tier catalogue label, erecting a powerhouse that enjoyed an extended stretch near the top of fashion’s roller coaster. That stretch made Drexler rich—or richer, anyway. It made Lyons famous: she is as recognizable as Donna Karan, Vera Wang, or Tory Burch, women with their own names on their doors. And in what had been a dead zone between designer and mass fashion, it gave American shoppers a conveniently located, approachably priced land of not-so-basics (peppy, preppy cropped Minnie trousers; slim Tippi sweaters) with real mojo (sequin-dappled tanks, cropped jacquard party pants)—so much so that buying them could feel a little like buying, and buying into, Fashion, or something convincingly close to it. For a time, J. Crew conjured a blend of relevance and emotional resonance that any brand, at any price, would kill to achieve.

But as anyone who has entered a J. Crew store recently can tell you—and as many insiders asserted in interviews— the only discernible feeling the company has evoked in recent months is ennui. The clothes and the imagery that once made them covetable have become ho-hum, somehow drained of spirit. And the headlines surrounding the company have been even worse. Since 2014, J. Crew has been steadily clacking back down the tracks it once ascended, shedding money and influence, not to mention executives—most notably in 2017, with the exit of Lyons, Drexler, and longtime men’s-wear designer Frank Muytjens. When that losing streak continued this past November, with the departure of the guy who’d been brought in to fix it, C.E.O. Jim Brett—who lasted a mere 16 months—the forecast appeared ominous. Brett’s tenure had been tumultuous and, to a team still loyal to Drexler and Lyons, bruising; senior employees report feeling as if they had a new boss every week. After Brett left, the company spent months in a no-man’s land, run by a committee of executives described rather uninspiringly as the “office of the C.E.O.,” its fashions designed until this past winter by Johanna Uurasjarvi, whose imprimatur, even to many inside the company, was hardly felt. All of which seemed possibly irrelevant anyway, given rumblings in the business press about an insurmountable debt that, according to a source in a Washington Post article, makes any turnaround plans the equivalent of “rearranging deck chairs on the Titanic.” In addition to that nearly $2 billion debt load, the company reported a net income loss of $120 million for the last fiscal year.