Unsurprisingly, Monday came and went without any word from Anna.
The prolonged back-and-forth kept playing out in the background, while I made a simultaneous effort to put my energy toward the people in my life whom I really cared about. For me and many of my best friends, the time from our late twenties to our early thirties was a period of major transition. Kate was newly married. My other best friend, Taylor, had just gotten engaged. My friend Holly was to be wed within the month. Liz had just bought a condo. And Kayla was the first in my friend group to become pregnant. Something in my experience with Anna deepened my understanding of relationships, and reminded me how important it is to show up for the people you love. Financially, I was so deep in the hole that buying a flight to San Francisco for later in the month—to celebrate Taylor’s engagement and to attend Kayla’s baby shower—felt like a small drop in a big bucket. These people, these friendships, and these milestones were my priority, and I wanted to honor them through my actions.
By the end of the following week, I had recovered enough strength to resume communication with Anna. Still haven’t heard anything, I nudged.
She responded at half past three that afternoon to say that she was sorry for the delay.
It’s been four months, I replied. “Sorry for the delay” hardly seemed sufficient.
Are you back yet? I asked.
No, she replied.
I wish we could just go to a bank and get this over with. I’ll be in CA soon—will you be in LA?
I’ll let you know, she answered.
When? What are you doing now?
I’ll be here for another week or [a] bit longer, she said.
In LA you mean? I’ll be out the first week in Oct.
Yes, she confirmed.
Officer McCaffrey was impressed with my progress, but even so, it began to weigh on me. Unlike Anna, I saw trust in a relationship as a value to honor, not to exploit, and as terrible as she had been to me, to break that trust from my side felt unnatural. Nevertheless, I went on.
I haven’t seen you in ages. Are you ok? I asked.
I was in ny the whole time until end of august, dont recall hearing from you then, she replied.
Anna, I was so intensely frustrated and mad at you. I had to distance myself. This has been so dark for me. I was tired of running in circles so I told you to contact me when we could talk about me actually receiving reimbursement . . . and then I didn’t hear from you. I’ve found ways to cope but the past four months have been hell. Please understand how awful this has been. I understand there may be circumstances beyond your control but this debt has never been something I was able to sustain.
Thirty minutes later, she replied: I wasn’t having the best time either as you might have noticed. Nothing worked out the way I planned and for you to assume any of this was my intention is insulting and disappointing. Considering the time we spent together, I thought you’d be able to see through the situation without sourcing outside input from people who barely know me. In any case, I’m looking [forward to] settling this with you as soon as possible.
There was an element to her approach that felt familiar. I scrolled through our recent exchanges—had she borrowed that “I’ve spent so much time with you” tactic from me?
I was desperate. I’m sorry for that, I told her. This whole situation makes me intensely sad.
She responded: Obv im not using this as an excuse for the delay with your repayment, it’s a separate thing.
Officer McCaffrey was shocked that Anna was so talkative. To me, her loquaciousness confirmed what I’d always suspected: that she was inherently lonely. This tugged at my sympathy just as it always had, but still I moved forward. Now that she and I had worked through our trust issues, it was time for a lighter approach. I made a comment about the weather in Los Angeles versus the weather in New York.
The weather is the least of my concerns honestly, she replied. Just trying to work things out back to normal.
Back to normal? Ha. You and me both, I answered. I’ve been struggling to get out of bed.
How is everything else? she asked. Hope you didn’t get in much trouble with your job. How could she not realize? There was nothing in my life that was untouched by the immensity of my ongoing stress. Obviously she didn’t understand the weight of the damage she’d caused. Her desire for connection, to some degree, felt real, but she seemed to lack the internal chip that would allow her to comprehend another person’s feelings. Officer McCaffrey encouraged me to downplay the damage, to avoid scaring her away. I told her about Graydon’s departure and spared her my incredulity.
Then I shifted the focus back to her: Are you feeling better? Why were you in the hospital? If you don’t mind my asking.
I will tell [you] later in person eventually, Anna replied.
I’d ask if you’re doing ok but I guess it sounds like you’re working on it. Do you have a nice place to stay for now at least?
Her answer dodged my question: Yes a little break from ny helped.
You have friends to hang out with in LA at least? I probed. I feel like you’re such a New Yorker. With all your black clothes.
A couple, she conceded. Also not drinking for couple weeks now.
That week, I’d received a random invitation to rapper/TV personality Action Bronson’s book-launch event. Remembering how much Anna had liked him, I shared a screenshot of the email with her and said it was too bad she wasn’t around. We were back in familiar territory, texting like old pals. We ignored the world closing in around us, but it was only a matter of time. Each of us had our secrets. I was no longer the naïf, but I kept up the guise in order to trick the trickster.
What day are you coming to LA? Anna asked me. For the New Establishment thing right?
A perfect opening. Yeah, either Sept 30 or Oct 1. Probably the 1st. I think I’ll be at the Four Seasons, maybe [the] Chateau. Where are you staying?
I’m in Malibu for now, she said.
Chapter 18
Passages
* * *
Malibu. Where would Anna stay in Malibu? I was driven to finish the puzzle, and its final pieces were coming together faster than I even realized. On Monday morning, the week before my trip to Los Angeles, Anna and I continued our conversation.
Where are you staying? Are you going to be there for the next week? Or are you coming back to NY sooner? I asked, letting her know that I would arrive on Sunday.
I think I will still be in Malibu, she answered.
I wish my Soho House membership included the one in Malibu, I said, to keep the conversation light. The more we chatted, the more comfortable we became with each other.
Apparently it’s for residents only, Anna replied.
Yeah, exactly. Blah. Last time I was in Malibu I stayed at Malibu Beach Inn, right next to Nobu It’s nice to be so close to the beach. I thought maybe this time she’d take the bait, respond to something in my commentary that would hint at her location. But after almost four hours of silence, I was afraid I’d overstepped, so my next message served as a chaser: Had sushi on the brain so I just had it for lunch.
She replied within the hour: Let’s try to get together in LA next week.
* * *
What did I think was going to happen? Hadn’t this been the goal? Momentum was building, and yet, as the investigation moved toward its conclusion, I was uneasy. Why did I have to be the one to betray her? And would she know that it was me? Anna had flipped a switch and become the character I knew before Morocco. Her reversal messed with my head.
Once again, I felt like a person whom she had chosen to trust—like I had in the beginning, when she picked me as her friend. But I had trusted Anna, and look where that got me? Was my hesitation an indicator that I was still susceptible to her influence? Knowing as much as I did and still feeling pity, I imagined what might happen to others who knew far less. Still, I didn’t want to do it. I wanted out of the situation entirely, but I was stuck—damned if I did, damned if I didn’t. Fo
r the time being, I could only keep moving forward.
When Anna called that afternoon, I was coming from the office, on my way to take the ferry from Wall Street to Brooklyn for dinner. I answered spontaneously, emboldened by her opportune timing as I walked, ahead of schedule, along the East River toward the pier. Her voice was exactly as I remembered it, distinct and high-pitched. Her tone was casual, unaffected by the dramatic tension of our recent past. It was astonishing how quickly we slid into our old dynamic: two friends catching up on the phone.
“I’m in rehab,” she confided. She was supposed to be there for thirty days, she explained, and she had been there for two weeks already.
“I’m glad you’re getting help,” I replied. For some reason, I didn’t ask what for. Maybe I assumed it was alcohol, or maybe I believed she was really just there to hide from the authorities, and meet other people who she could potentially con. “Do you get to go to the beach much?” I asked, homing in on her location.
“Yeah,” she confirmed, “they offer beach walks.” The center was just across the Pacific Coast Highway.
How else did she pass the time, I asked—were there tennis courts on the property?
There were, she answered, but lately she’d taken up golf. The facility had a relationship with a country club in Calabasas.
And whom did she play with, I pressed.
She had made a few friends, she told me.
Anna had entered an enclosed center that catered to the wealthiest people in their most vulnerable state—of course she had made a few friends.
After less than ten minutes, the call dropped, and Anna texted to say that she was off to her next activity. I studied my notes from the conversation and began to do my research.
* * *
A fair number of luxury rehab centers dotted the stretch of the Pacific Coast Highway near Malibu, but Officer McCaffrey and I focused on two, Promises and Passages, both of which closely resembled Anna’s descriptions. Costing upward of $60,000 per month, the latter billed itself as the world’s most luxurious addiction rehab center—and as such, for Anna, it seemed the likeliest choice.
Even though it felt like we were getting close, due to health care privacy regulations it wasn’t so easy to check. Clinics were not required to admit law enforcement officials, nor to confirm whether a certain person was in residence. Assuming Anna knew as much, you had to give her credit.
* * *
The final week of planning for the New Establishment Summit was the most intense. Kathryn’s assistant, Emily, and I stayed in the office until eleven p.m. almost every night. We wrapped up travel bookings and compiled scheduling documents. Once we were in Los Angeles, Monday would involve a full day of prepping, and the portrait itself would be broken up over the course of the two-day conference, on Tuesday and Wednesday. For each of the people to be photographed by Annie—Ava DuVernay, Maja Hoffmann, Anjelica Huston, Bob Iger, John Kerry, Richard Plepler, Shonda Rhimes, and more than fifty others—Emily wrote out a short bio and gathered recent news for quick reference. Using headshots, I created a visual timeline for the shoot and then spent hours cobbling together supplemental research. By the time we landed in Los Angeles on Sunday afternoon, October 1, we were bleary-eyed but ready.
We switched on our phones after the flight to discover a company-wide email announcing that S. I. Newhouse, Jr., the chairman emeritus of Condé Nast, had died. I found a photograph of “Si,” as he was known, taken by Jonathan Becker at the Vanity Fair Oscar party in 2000 and posted it to the V.F. photo department’s Instagram account, choosing a quote from Graydon for the caption: With [Si’s] passing, at the age of 89, so goes the last of the great visionaries of the magazine business. I was witness to an empire in transition.
Emily and I went directly from LAX to the Wallis Annenberg Center to help with the “load-in” and begin to set up. Two hours later, I was doing laps between our equipment holding room and the portrait site—firing off messages concerning a rental car, parking, raw almonds, wire baskets, a cooler with ice, water for the crew, and thumbtacks—when I received a message from Anna asking if I’d arrived. Yes, I told her.
Nice, where are you staying?
The Four Seasons, I answered, but haven’t been to the hotel yet. You still in your place? I asked. It’s not Passages is it?
Yes I am, she replied. Pls don’t tell anyone though.
That place is supposed to be the best, I volunteered.
You can come visit, she deigned.
Anna seemed genuinely to miss our friendship. I was back in her favor.
Come visit today, she said again, offering to send a car.
There was just so much that she did not care to understand. Evidently, to her, my needs were an inconvenience.
I don’t think I will have time to come to Malibu, I answered. Are you free to come to Beverly Hills anytime in the next few days?
Let me know your times, she said.
Could we do lunch on [October] 3rd?
Sure, she replied.
Nothing about this was easy. It seemed like Anna was sincerely happy that we were making plans again, and no matter how shallow she was, that weighed on my heart. Surely, there were elements to our friendship that contained some degree of authenticity. But what were they and what were they worth? For all I knew, everything was counterfeit—it’s not as though Anna ever trusted me enough to reveal the core untruths that propped her up.
* * *
Annie Leibovitz landed in Los Angeles on Monday morning, October 2. She came directly to the conference site and commenced with a full day of prep. Her large group portrait would be taken on an exterior set of wide steps adjacent to North Crescent Drive. Based on timing, and the research we’d compiled, she worked with Kathryn to map out a plan—deciding where each of the subjects would sit or stand within the composition.
I was working when I received another text from Anna: Do you have time to come over to Malibu today by any chance? I need something from the outside. Again, she offered to arrange for my car.
I’m on site all day, I replied. What do you need?
She asked me to give her a call. I said that I would in just a few minutes.
Around the corner, and out of the way, I first phoned Officer McCaffrey. It was the eleventh hour and I had doubts, not about whether Anna would show up to our lunch date—I was sure that she would—but about my willingness to proceed. What did I care if Anna got arrested? Whether she did or she didn’t, the damage was already done. It wasn’t going to reverse time, eliminate my stress, or restore my finances. Vengeance had never been my motive. For a long time Anna had scared me, but closer up she seemed less threatening. I harbored some lasting ill will, but how deep did it go? Was I really willing to instigate her incarceration?
Wasn’t the surest way to clear Anna from my life simply to cut ties altogether? Was it possible to forgive her, to step back, and to move on? I’d come so far, but now I was hesitating, second-guessing.
The hardest obstacles to overcome were deep within myself: irrational loyalty, compassion, and passivity—collectively these were forms of self-sacrifice. Where did they come from? And how did they mark me? As naive? Damaged? Oh, how I hated the sensitive part of me that continued to make excuses for Anna, this person who had willfully dragged me through hell. Except it was this same sensitivity that set me and Anna apart. Even if empathy was partially to blame for my predicament, I had no wish to be without it. It was a weakness, but it was also a strength. I saw fellow people where Anna saw only pawns.
“Is this the only way she makes her money?” I asked Officer McCaffrey.
As far as he knew, deceit was her sole source of income.
* * *
Next, I called Anna. She asked if I would be willing to buy a large bottle of vodka and some bottles of Voss water, then pour out the water, transfer the vodka into the empty Voss containers, and finally bring the disguised vodka into her rehab in Malibu.
No, I told her. For starters, I was too
busy with my job to leave, grocery shop, and spend hours in traffic driving from Beverly Hills to Malibu and back. So she came up with another plan. What if she had a courier do the grocery shopping? He could bring the items to me, I would repackage them at the Annenberg Center, give them back to the courier, and he would bring them to her.
“Is it even for you?” I asked.
“No, I don’t do vodka,” she said.
I wanted no part of it. I told her that the Annenberg Center was swarming with security. It would be much too difficult for a random courier to gain entrance, and I didn’t have time to loiter around awaiting his arrival. It just couldn’t happen. Catching myself, in an effort not to sound overly judgmental given the circumstances, I suggested that maybe we could figure it out tomorrow. She got off the phone quickly once she accepted that I wasn’t going to help.
Back at the group-portrait site, I was seated on a lower step, leaning forward, elbows on my knees, holding very still. One at a time, other makeshift stand-ins moved into place around me. We relaxed in position as Annie studied our arrangement and her photo assistants checked the lighting. My cell phone buzzed at random, tucked within my back pocket. I ignored it until a break in the blocking session, and then pulled it out to check my messages.
How much time do you have for lunch tomorrow? Anna asked.
One and a half hours, I told her. (It wasn’t true, but it didn’t matter.)
Ok noon it is, she wrote back. You choose the spot.
I suggested a restaurant called Joan’s on Third.
Ok, she said. Do we need a reservation?
I sent a screenshot to Officer McCaffrey. Awesome, he replied, she can make one if she wants.
Maybe make one? I’m not sure, I said to Anna.
They don’t take any, she replied.
I think it’s pretty casual, I answered. They have delicious salads.
My Friend Anna Page 24