It is late-fall in New York and I’m in a flap of a mood having found a stack of rare and original papers in Columbia’s Butler Library with titles like “The Notebooks of F. Scott Fitzgerald” and “Conversations with F. Scott Fitzgerald”. The best of the writings deal with Fitzgerald before Zelda and, in the coming freeze of the season, I like hearing from the man himself about how he held together through hot transitions, time, and matters of the heart. Fitzgerald knew something about pain.

On the sledding slopes of St. Paul, Minnesota in 1915, Fitzgerald met and fell in love not with Zelda, but with Ginevra King. King, by her own report and the account that constitutes nearly all of Fitzgerald’s work—all those dreamy, desultory women—loved him too. They sent letters to each other. Fitzgerald intended to marry the slick socialite. But the self-described “fickely” took a sudden, sodden turn, saying a sudden yes to proposal of marriage from Chicago tycoon William Mitchell. Some say, for better or for worse, Fitzgerald was never the same. It was a, if not the, signal experience.

When they could speak again, King agreed to Fitzgerald’s request that she destroy everything he had ever written to her and, for the most part, she did.

But a 1918 letter Fitzgerald wrote congratulating King on her engagement survives. “Doesn’t it make you sigh with relief to be settled and think of all the men you escaped marrying?” he wrote. “As Ever, Scott.”

Scott, for his part, kept every last one of her letters, fastidiously binding them with a cover he marked “Personal Letters: Property of F. Scott Fitzgerald (Not Manuscript.)”

Real heartbreak is tenacious. Unrelenting. Two decades and three children later, King met up with Fitzgerald who, by that point, was already famous– the undisputed darling of the American literary set– and living in Hollywood. He was, also, deep in the gin. In his early 40s, Fitzgerald was nearing the end of his life. King asked him about the extent to which she might have inspired his work, The Beautiful and the Damned.

“Which bitch do you think you are?” the reply. The barstool nearly gave way beneath him. They did not meet again.

But this, too, is a kind of love. The question, as response, is in fact an absolute statement of love. A full admission of the loving, laborious work of preservation– King’s preservation within Fitzgerald’s letters and work.

It is possible to feel pain for decades. There are forms of pain that last a lifetime, and one can revel in it, locate it again, even swear at it. Swear by it. Righteously fall off barstools in front of it. Fitzgerald made that commitment. Steadfast. Zelda was and would remain forever an afterthought.

The year Fitzgerald lost King and embarked on the road of dedicated pain-commitment, the writer joined the US Army. He was stationed down near Montgomery, AL, where he met, yes, Zelda Sayre, daughter of an Alabama Supreme Court judge. Cue end of Army. Cue move to New York. Cue Fitzgerald shoe-leathering look for a job as a reporter by day, exploring the many permutations of gin fizz by night. No papers bit.

Drinking hard, and Zelda was too, things fell apart. It looks like it was more down to the $90 a month wage Fitzgerald had begun earning as a hack, nothing ad writer. You can’t keep in New York highballs for long with that kind of cash, then as now.

The question of money. Fitzgerald became haunted by the financial outs of his early life, especially after his father lost the family’s furniture business. But he likely exaggerated his own sense of economic disparity, even as a perceived link between money and romantic fulfillment never, ever left him. A stanza from his Princeton notebooks (Firestone Library: Collection 1143, Lot 135):

Those wealthy goats
In raccoon coats
can wolf you away from me.

“On the Fourth of July, utterly disgusted with myself and all the editors, I went to St. Paul and informed family and friends that I had given up my position and had come home to write a novel,” Fitzgerald recounted in an interview with Charles Baldwin. “They nodded politely, changed the subject, and spoke of me very gently.”

So no King and now Zelda-free, Fitzgerald headed home to his parents’ house in St. Paul. (We’re skipping a lot of pain here and time alone and notes pinned to curtains and solo meals of ham and peanut butter, all of which is known to be true but moving on, always on). It was here that Fitzgerald turned finally, seriously, toward writing. Really writing. The work of it. The question of consistency. Presence. In short order, Fitzgerald finished a 120,000 word manuscript that would be his first published novel, This Side of Paradise.

Again in New York and a (re)made man, the writer quickly emerged as the toast of the literary set. Zelda quickly revised earlier misgivings about Fitzgerald and, yes, rushed to his side.

Maybe vindicated, maybe able to swab away some of those battle scars left behind by his competitors– those richer men– or perhaps just loosened up by success and, well, gin (ever more) gin, Fitzgerald let fly on women:

“I know that after a few moments of inane conversation with most girls I get so bored,” the writer told B.F. Wilson in a 1923 Metropolitan Magazine interview. “Unless I have a few drinks I have to leave the room.

Further, Fitzgerald goaded Wilson to concur with him. Come on, Fitzgerald seemed to be saying. Women are just such a chore. A toy. A bad joke. But forget what he seemed to be saying. Here’s what he actually said:

“‘Be perfectly frank now, don’t you think men are much nicer than women? Don’t you find them more open and aboveboard, more truthful and more sincere? Wouldn’t you a whole lot rather be with a bunch of men than with a group of women?’”

“I had to confess to the impeachment,” Wilson wrote in his article.

Zelda floated into the room. “He says that all women over thirty-five should be murdered,” she said.

Zelda, among her innumerable skills, was a known and expert winker.

Narrowly averting homicide, the pair continued on their upward trajectory of parties, gimlets and Fitzgerald’s completion of a new novel that satisfied him in everything but name. Possible titles included Among Ash-Heaps and Millionaires; Trimalchio; Trimalchio in West Egg; On the Road to West Egg; Under the Red, White, and Blue; The High-Bouncing Lover, and on and on.

Fitzgerald wrote what would be his best-known work–the novel finally branded The Great Gatsby–in 10 months flat. The man was 28 years old.

The ebb of that trajectory featured writer’s block, drinks, more drinks… (let’s have a few more drinks… get me a drink after this, will ya?… To hell with the women, let’s drink) together with Zelda’s engagement in some manic ballet that came paired with two rounds institutionalization, the second one permanent.

“I left my capacity for hoping on the little roads that led to Zelda’s sanitarium,” Fitzgerald wrote of her final commitment.

I want to think about these people and this history because I am concerned about the prospect of being hurt or scarred or knocked down for such a long time, perhaps for life, and the prospect that that nasty old scar, that ragged old thing, might not be so bad: might be, in its own way, a salve.

Fitzgerald the drinking misogynist was equally the sledding romantic who had to endure the quizzical return and then fat-out denial of King, the first woman he ever really loved. On the heels of this total unraveling of Zelda, arguably his second greatest love coupled with perhaps his greatest act of courage, Fitzy-G faced off against the gentle condescension of friends and family as he trudged back to his childhood bedroom, possessed with the conceptualization and drafting of his first full novel, itself so rarely an endeavor that leads to boastful toasts.

But he did it.

Maybe the best material is located in our greatest pains and traumas and you’d have to be half-mad to pursue it but, for those brave enough to climb back up the stairs to our childhood bedrooms—or wherever the thing may have happened, on whatever loose and wild sledding slopes or hard mountain faces—to create. Indeed, you’d have to be entirely mad not to.

In one of her final letters to him, Fitzgerald’s once and former love Ginevra King wrote, “Last night I dreamed you were calling on me, but it went off all right. Only you had purple hair and would insist upon strutting around. You were tapping on all the walls.”