My sister, Jill, is brilliant—a Phi Beta Kappa and a graduate, like me, of New York City's Stuyvesant High School. She regularly scores over 400 in Scrabble and can race through the Sunday Times crossword. She reads and writes in four languages, plays Beethoven's Emperor Concerto on the piano, and devours classics and contemporary literature. But none of that has protected her from a life of drug addiction, mental illness, and homelessness.

"How come you're different?" my mother once asked me, meaning why wasn't I afflicted by addiction as well? Our mother's mother, Jill's and my "Grandmaman," was toxic in body and mind, a bottle-of-bourbon-a-day alcoholic. Perhaps addiction was a recessive gene in our family. "I'll think about tomorrow," I told my mother, who also never suffered from addiction. I don't think either of us had an answer apart from genetics.

I used to want to be just like my sister

Jill's lifetime of drug use has shaped not just her life but much of mine.

Jill went to junior high at a fancy prep school in Manhattan where drugs were ubiquitous. She experimented — and introduced me to drugs. For me, the next day's recovery seemed to take up too much time. Instead, I enjoyed Jill's war stories — how the soil in a planter box came alive one time after she took belladonna; how a friend's hair turned to lightning rods one time while Jill was tripping on acid. Still, people mistook us for one another; I remember how proud I felt one time when I was in junior high and Jill in high school, and a mutual acquaintance ran up to me in Central Park with a joint in her hand and hugged me. "Jill!" she cried.

"You're all drunk and tripping," our mother ranted one time when we were both in high school, upon walking in on the two of us during a party in our living room hosted by Jill. Our mother lifted her arms in the air, shook her head dramatically, and retreated to her bedroom. Our mother often said she thought we'd grow out of our self-destructive behavior. She also said she was thankful we were doing drugs at home and not out on the streets.

I realized she had a serious drug problem

The fact of Jill's addiction came into focus for me when I was in my late 20s and she was about 30. It was the early ‘90s; the echo of Kurt Cobain's guitar had migrated to New York City, and heroin was de rigueur at the Lower East Side clubs. A talented guitarist and singer, Jill haunted that scene. I enjoyed going out with her and even tried heroin once — though in my case I threw up, fell asleep for 24 hours, and missed work for a week.

After that, I limited myself to observation. There was a dealer in the basement of a bodega on East 12th Street, Jill told me; you went underground through a tunnel and entered a bathroom, where you knocked on a medicine cabinet; the mirror swung open and a hand emerged offering a baggie of dope. At the El Sombrero Mexican restaurant on Ludlow Street — "the Hat" — you could smoke H in the bathroom and sit forever at a table where you'd see other acquaintances also nodding and never ordering food.

Some people exist breezily in such a world without ever succumbing to the temptation for everlasting euphoria or escape — me, for instance. But for Jill, drugs perhaps salved some wound. At a Thanksgiving during that era, Jill went seemingly blank for an extended moment, her eyes shut, the contents of her plate spilling to the floor. Soon after that, we visited our father and his second family up in Boston, and Jill went out and returned with two six-packs and slurred speech. I knew what other family members seemed to be denying or ignoring or, in the case of our mother, blatantly rejecting. When, one time, I tried to talk to my mother about it, she accused me, "Why are you so hard on Jill?"

And I discovered I didn't want to be like her anymore

Like little sisters everywhere, I'd admired my older sister and emulated her. Perhaps this was why I took her fall so hard, why I felt abandoned. Like our mother, Jill was exotic — ballsy and gorgeous. I'd adopted not only her quirks and mannerisms but her worldview. I copied her emotional fragility — the meltdowns, the weeks of consuming sadness. Like Jill, I harbored anger and resentment. Our father was often the target, for favoring his children by his second wife, for making us feel shame for our second-class position in our family. I borrowed Jill's general aura of detached, sometimes humorous fatalism.

But then one day, Jill vented on the telephone to me about our father. It occurred to me that if it wouldn't kill Jill, bearing her disposition would certainly kill me. I needed to stop thinking about what was wrong in my life and focus on the positive. I wanted to stop brooding. I wanted to heal.

In 1995, Jill had a series of outbursts at her job in book publishing, and her supervisor asked her to take a mental health leave. Jill claimed the leave was unwarranted, and she quit instead. I'm not sure Jill considered the possibility she had mental health issues at all until 1997, when at age 34 she entered counseling for addiction during her first attempt at recovery. She began speaking of her issues with chronic pain and depression.

After that, Jill moved in with our mother and joined a methadone maintenance and counseling program at Bellevue Hospital.

Later, there were more telephone rants, Jill’s fury sometimes directed at me. She began taking benzodiazepines, which when mixed with methadone can bring on an opioid euphoria and, like heroin, addiction. When I asked her to seek more help for her drug use, she called me self-righteous and superior. I was making a living as a writer; Jill was still unemployed. She said she resented my success at life, that I made her feel like a loser. I worked hard to avoid guilt or a creeping sensation that I was implicated in her downfall or should fall alongside her in solidarity. I tried to nourish rather than diminish my drive to succeed. I believed she wished me failure.

I began to see Jill only when I visited my mother. There were ups and downs. She apologized, began consenting agreeably when I made suggestions but often without actually taking them. She'd flare up again.

I wonder what I would have done differently if I’d accepted the reality of her depression earlier. I imagined I was helping each time I begged her to attend recovery or when I did the research to discover good programs or ways to pay for them. I attended Al-Anon and learned that one must strike a balance between detaching and enabling, that one should strive toward a stance someplace in the middle, of loving strength. For me, the pain of the situation led to frustration and distance. Perhaps I would have found a more elegant middle ground if I’d accepted from an earlier age that I was not Jill, much as I wanted to be. Freeing myself from that thinking would have allowed me to see the more important truth: that Jill was not me.

The defining moment

Things were unstable if predictable in our family, Jill continuing to live with our mother, until one day in June 2011. I got a call from someone who'd been buzzing over an hour at the apartment in Long Island City, Queens, shared by Jill and our mother — who had by now been diagnosed with mid-stage Alzheimer's. I rushed over. Inside, our mother followed me as we entered their shared bedroom. Jill was in a deep sleep on her bed with blood on her wrists; my mother sat down on the adjacent twin bed and looked over with an expression of confounded worry; she stared at me, stared at my sister, frowned, asked me what was going on.

I reached out to touch Jill's shoulder, my body operating as if in slow motion. She shook awake, which startled me and — for a second, anyway — allayed my panic. Had she taken pills, I thought to ask her. Jill spoke as if from underground. She'd cut herself with a broken glass at the sink, she said. She was tired. I didn't understand what it was like to be her, she added, and then she went back to sleep.

This defining moment would reverberate in our family for years to come, but it was weeks, even months, before I grasped that. Perhaps she was right that I'd mistakenly thought I understood her. I managed to get a call out to Jill's counselor at her methadone program at Bellevue. Over the course of the day, Jill and her counselor made plans to admit Jill at Bellevue's mental health ward for depression. Her counselor deemed her attempt to "take her life" with pills and a broken glass not serious — but it was a warning.

I wonder what I would have done differently if I'd accepted the reality of her depression earlier

The problem was not resolved, but I moved on to the more imminent need: making arrangements for home care for our mother now that Jill would no longer be home with her to watch her. Though, really, who had been watching whom?

As it turned out, Jill's plan couldn't avert the next disaster. The next morning I was back across town, and Jill went out to do an errand in preparation for her hospital stay. By the time she returned home, our mother had gone missing. We couldn't locate her until a doctor at the ER at Elmhurst Hospital in Queens called that night to say she'd been there since the afternoon. My mother hadn't been able to provide her name or address, but the doctor recognized her from a previous stay. The hospital's care team, finally able to reach me, informed me what I already knew: Our mother couldn't safely stay at her apartment.

For Jill, bad luck had led to bad choices had led to more bad luck one too many times. My mother would move to an assisted living in Brooklyn. Neither Jill nor I nor our mother could afford the apartment. Our mother would have to give up her home — Jill's home, as well.

Because of her drug use, Jill had either kept her distance from other family members or alienated them, as she had me. Our mother's illness had brought me closer to Jill again. But at that crossroads in 2011, taking her into my home was out of the question: I didn't have the space, Jill didn't want to move in with me, and most, though I loved my sister, I didn't trust the addict.

Jill's place of residence became her bed at the Bellevue mental health ward. She was 47.

Jill's harrowing years in New York City's homeless shelters

Jill was not discharged from Bellevue until September 2011, after a delay of several weeks while her counselors worked with her to find her "a bed" — as a free spot to live is euphemestically called for the homeless. The next several months passed tumultuously for Jill, but my own focus was elsewhere: Our mother was dying.

Our mother's assisted living began sending her almost weekly to the various hospitals in Brooklyn for issues untreatable by their nonmedical staff; those issues often revolved around their desire to have her medicated. While I attempted to advocate for our mother and refuse additional drugs for her, Jill moved from Bellevue to a one-month rehab in Poughkeepsie. She was discharged with a referral to a so-called three-quarter house called Narco Freedom in the South Bronx, whose operators have since been sent to jail and indicted on charges of taking kickbacks and perpetrating Medicaid fraud. The house offered its own Medicaid-funded methadone maintenance program and counseling, and in fact required its residents attend it — which was the nature of the fraud. Jill didn't discover this until she arrived, however, and, wanting to continue her positive relationship with the counselor and program at Bellevue, refused to shift her Medicaid funding. Her only alternative was to leave.

I let my job suffer as I made contact after contact trying to help my mother and Jill

Jill next checked herself in at the city's intake shelter for women in Jamaica, Queens, and two days later was given a permanent shelter assignment at the Park Slope Women's Shelter, which is sandwiched into a section of the beautiful and historic Armory on Eighth Avenue. A third-floor apartment across the street is listed for sale today at $1.15 million. The Department of Homeless Services' annual performance rankings praise a handful of women's shelters, and Park Slope Women's ranked fourth out of 20 shelters for single women that year. Still, come winter, Jill told me that life was just too hard in the shelter, and she was finding it hard to stay off benzos. She was addicted, she said, and wanted to detox and reenter a long-term rehab. She went back to Poughkeepsie, then a month later returned to Park Slope Women's, and it wasn't another few months before she called me again to tell me the same thing. She was depressed, life was too hard, and she was thinking about going back to the rehab.

Then in October 2012, Hurricane Sandy struck. Jill had been in the shelter system a year, and our mother, too, had survived those months in institutional living. Both were in crisis. It was as if chaos swirled in every corner of the sky above me. I sealed all my windows and got under the covers.

At about midnight my mother's assisted living called me to say they'd moved all the residents to another assisted living further inland in Brooklyn. Then another call came saying that my mother, disoriented in the new location, had refused to cooperate and had been sent to Maimonides Hospital in Brooklyn. I called Maimonides, and she wasn't there. I located her two days later, at Methodist Hospital in Brooklyn, 10 blocks from Jill's shelter in Park Slope. Except Jill wasn't there — she'd disappeared, too.

Jill didn't turn up again for four weeks. A bank account I managed for her went stagnant, showing one ATM withdrawal near Poughkeepsie the night before the storm, and then nothing. Our father had kept his distance from Jill after several telephone tirades and one drug arrest; he was in the habit of expressing his concern by giving me money for her here and there, and by calling me and asking why Jill couldn't just get a job. Now even he began calling daily to encourage me to track Jill down. Part of me knew she'd gone to rehab, but part of me thought she'd been swept up in the storm, and part of me thought she'd gotten depressed and dived in the ocean with heavy boots on.

Jill called a month later, having returned to her permanent shelter in Park Slope. "Oh, sorry, I thought I told you I was going to rehab."

"I thought you were dead."

"I'm sorry."

Those were the easier days for Jill, if not for me. My phone and email records from the time show that I let my job suffer as I made contact after contact trying to help my mother and Jill.

Our mother never left Methodist. Even as I fought with the staff to resist her overmedication, she fell one night, sedated, while an attendant helped her from bed, and she broke her hip. Rehab went slowly. Jill visited her daily, and then one night the hospital called to say our mother had contracted fatal pneumonia. According to the doctor's prognosis, our mother had three to 10 days of life left barring interventions, which she'd refused in her advance directives.

Jill and I took turns sitting with our mother. One day during our death watch I bought a pocket radio at the Radio Shack across the street on Seventh Avenue, so our mother could listen to her favorite classical music. Her last words came during Mozart's bassoon concerto in B flat major: "That's nice."

Not long after, Jill relapsed again into benzodiazepine abuse and left the shelter in Park Slope to enroll, once again, at a rehab. After she was discharged, she ended up at a different shelter, one that was ranked third from the bottom of 20 shelters for single women. And for good reason: Over her nine months there, Jill described urine puddles and stacks of garbage at the elevator doors on each floor, particularly on weekends when the facility was short-staffed. Guards, counselors, housing aides, and desk clerks were hostile. Mail was intercepted or lost, including the all-too-common yet arbitrary notices to submit new qualifying documents in person at the Medicaid office.

One day, Jill intentionally missed curfew in order to get her shelter assignment switched, and succeeded in receiving a new assignment in Crown Heights. This proved equally dysfunctional, throwing hurdles in the path of survival at every turn. Jill's locker was burgled one day while she was attending her program at Bellevue. She lost all her medications, including antidepressants; Neurontin, for pain; and Seroquel, for sleep. She went to her clinic to ask for replacement prescriptions but was denied because of her history of pill abuse. She called to make an appointment with her psychiatrist and was told she could walk in, but when she walked in, on a weekend, was told she needed an appointment. She went to the hospital emergency room but was told she'd have to admit herself for several days of observation before they'd consider a new prescription, and also that in the hospital they'd discontinue her methadone temporarily. Jill therefore went without, and became, not surprisingly, depressed.

The consequences were significant. The shelters are charged with helping residents locate permanent housing, but they require cooperation from their residents — for instance, residents must keep appointments for housing interviews, collate materials for their housing files, and stay abstinent. For the shelter resident facing such obstacles to everyday functioning, this is not easy. That week, Jill missed several housing appointments. She also overslept and missed her Saturday pickup for the weekend's methadone.

I'm walking a fine line between advocating for my sister and enabling her

By this time, I'd shifted my stance of detachment — but how to know where to draw the line to avoid enabling? I began to intervene for her. I called a friend who worked for an advocacy for mental health and asked for help getting Jill's Medicaid turned back on. I helped her recover prescriptions; I gave her warm clothing and last-minute cash; I organized her paperwork for an as-yet-unfiled Social Security Insurance application.

One time, she asked for cash because she was in a "life or death" emergency. I didn't ask for details — I didn't want to know. Was there a dispute over drugs? Did she score a Xanax because it was all so stressful? I gave her the cash. Later she explained that she'd overslept that Saturday and missed the window for her weekend-long supply of methadone. She faced withdrawal and a reprise of her chronic back pain. She'd needed the money to score heroin.

Now, was the H really necessary to ward away the withdrawal? Was there really no better solution? Should I have intervened further to create a better outcome? To what extent do I let her make mistakes on her own, or can I even prevent them?

I can't fix it — and Jill can't fix it on her own, either

I do know I can't fix this myself. It's funny, because it's something I've often told Jill over the course of our lives: "I can't fix it" — as if to convince both Jill and myself that I, the so-called functional sister, am nevertheless not capable of solving the world's problems. "I can't fix it," I used to tell Jill when our mother, still living in her apartment, would leave her keys in the oven, put cookies in the cat bowl, leave the stove on with the cat litter box on top of it. She'd brush her teeth with Lysol, defecate in the shower. As our mother’s Alzheimer’s progressed, I hired a home care aide, and the aide showed up late one time.

"What am I supposed to do?" Jill ranted at me. "I can't live like this."

"I can't fix it," I said.

I do wish I'd had greater perspective earlier on. I wish I'd convinced our father, as I finally seemed to after the Sandy episode, that just "getting a job" after 15 years' unemployment was not going to solve Jill's problems. I wish that the city's homeless services system put fewer roadblocks in the path of worthy recipients of aid, and that that worthiness wasn't judged on specifically the metrics that the homeless person is not able to reach.

What's most difficult for me is accepting that Jill can't fix things on her own either, that she has neither the tools nor the resourcefulness to take on the Sisyphean challenge before her. If I were in her situation I would act differently, but she is not I. The differences are too stark now to ignore this. No one runs up to us in Central Park with a joint anymore mistaking one for the other. I’m that university professor who argues with her son’s day care about the sugar content in breakfast cereal; Jill is the one who gets her cereal for free at the homeless shelter. Her four years in New York City’s shelter system have shown me more clearly how her lifelong mental illness makes it impossible to take charge of her troubles.

The key seems to be some middle pathway of availing herself of the support on hand while also helping herself.

That negotiation seems connected to a conversation Jill and I often repeat about whether addiction is a condition or a choice. Lately, I've come around to a point of view that accepts her as her own person and not a mirror of myself, that understands "choice" is not as simple for her.

She seems to be accepting a view that incorporates more personal responsibility. "I need to stay stopped, one hundred percent," she wrote me recently. "Not even once in a while. That's what I've managed to put together. About two months so far with no use. Hurray for me! I'm just tired of Xanax. I don't need to be tranquillized or high. And things always work out better for me when I'm clean."

This story was supported by the journalism nonprofit the Economic Hardship Reporting Project.

Elizabeth Kadetsky is author of a memoir (First There Is a Mountain, Little Brown), a story collection (The Poison that Purifies You, C&R Press) and a novella (On the Island at the Center of the Center of the World, Nouvella ). Her journalism and personal essays have appeared in the New York Times, the Nation, Ms., Antioch Review, and elsewhere, and her fiction has been included in the Pushcart Prizes, Best New American Voices, and the Best American Short Stories notable citations. She is assistant professor of creative writing at Penn State and can be found at ElizabethKadetsky.com.

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