The 50th New York Marathon

Dan Freedman
18 min readNov 16, 2021

Five Months of Training to Traverse Five Boroughs

The 50th running of the New York Marathon (courtesy NY Times)

A friend who has run a few marathons suggested that I jot down some notes and thoughts about my training and the race as quickly as possible, as with the fog of pain and the impermanence of memory, things will be lost like pre-race clothing strewn along the outer edges of the Verrazzano Bridge. So this is that. It is a skosh navel-gazy, but it is done as much for my personal posterity as anything else, so feel free to stop here or skim the rest.

Running a marathon has always been on my bucket list, but I never had the courage to try. About two years ago, I threw away my fears and signed up for the New York Marathon, only to have a global pandemic end that dream before training even began.

And then last January my stepson, Sam, was diagnosed with leukemia. With an incredible debt of gratitude to Children’s Hospital Los Angeles who treated him with compassion and care, and who guided him into remission, I considered participating in the Nautica Malibu Triathlon (my favorite event), which raises about $1M for CHLA every year. But my wife talked me out of it. She suggested I do something for the Leukemia & Lymphoma Society; and she scoped out various options. We (she?) landed on the Marine Corps Marathon in Washington, D.C. And so it began.

For reasons that I am still not entirely clear about, I was invited to join Team in Training, which is a running group for people with or touched by blood cancer. On Saturday, June 19th, I met the team for the first time in Griffith Park. Team in Training, I came to learn, is an incredible organization, and prior to each workout, someone shares a/their story. So after you wipe the tears from your eyes (and that happened every time), you stretch and run. I spotted this shirt upon my arrival that very first day, and I knew — at that moment — I would cross the finish line.

My training covered about 575 miles, through thirteen cities, across seven states, in two countries. I did 16 in the South Bay along the beach, and felt solid. I did 18 in Madison while visiting my son for Parents’ Weekend, and that one nearly broke me. It may have been a stomach bug, or the humidity, or a lack of preparedness, but whatever it was, I could barely walk out of the hotel afterwards. And I could not complete my recovery run the following day. That was my first crisis of confidence — maybe, at this age, I wasn’t cut out to run 18 (or more) miles.

I bounced back a few days later, banging out an easy 10, and then did the “Graduation 20” in Houston the following Saturday. In town for the Red Sox-Astros playoff game, I mapped out a path that took me through three colleges campuses and into Memorial Park. My navigation skills left me 0.4 shy, so I did one lap around Minute Maid Park to finish the distance. A cold bath, two Advil, and a flight home, and I felt pretty good. With 20 in the rearview mirror, the next real challenge was the big day.

It’s funny; before this process began, the longest I had ever run was 13.1 miles. I have completed many half marathons, always training beforehand. Upon finishing each race, I was exhausted and out of commission for a week. And now I still had a 12-miler ahead of me, and didn’t think anything of it. Time and distance get skewed when you run this much and this far.

Prior to my 18-miler, I received notice that the Marine Corps Marathon had been canceled “for safety reasons.” Putting aside that ambiguity, I was devastated. I had gone too far — and raised too much money — to stop now. Luckily, Team in Training and LLS were able to transfer my bib to…New York! After everything, New York was going to actually happen. I adjusted my training, pushing it back one week to account for the later race, and made plans to head to the city that never sleeps.

Unfortunately, the New York Marathon was just a few days after my stepson’s surgery, so my wife couldn’t make the trip. Shortly after Sam was diagnosed with leukemia, he suffered a bleed in his back that caused paralysis. The doctors performed emergency surgery to stop the bleeding. But, to do so, they had to cut out large chunks of his spine. He has since recovered — and regained the use of his legs — but he was left with a condition called kyphosis, which is a rounding of the spine. Although the initial surgery was successful, Sam now didn’t have enough spine to support his back. So, four days before the race, Sam had spinal fusion surgery, which went well. But my wife couldn’t leave his hospital room to stand three deep in Manhattan to root me on — she was exactly where she needed to be, right next to her boy.

The day after surgery, once I knew that Sam was comfortable and out of harm’s way, I headed to New York. My sister and I arrived on Thursday evening, and from the moment we checked into the hotel, you could feel a palpable buzz in the air. We didn’t know we were staying at a “marathon hotel,” but there was the “50th” logo lit on the wall of the lobby, and the pre-race Saturday night pasta dinner on offer in the hotel restaurant.

On Friday we went to the expo to collect my bib and various other odds and ends. All expos are essentially the same, but this one — like most things in New York — was bigger and more intense. We heard, time and again, that with last year’s event being canceled due to Covid, the city was ready to let loose on Sunday. As soon as we left the Javits Center, we noticed 50th Anniversary race gear everywhere. You just knew you were about to be part of something special.

On Saturday I did a shake-out run in Central Park. And there, too, people hit the loop in 2021 Marathon clothing, lest anyone think they were just out for a casual jog.

For the entire weekend, whenever you talked about the race with a New Yorker or a prior runner, they spoke about it with reverence. They explained how incredible the experience will be, how it is unlike anything you have ever done, and how you are going to have the BEST time. More and more, I truly came to believe it. And more than believe it, I felt it — I was incredibly emotional all weekend, thinking about all that Sam had been through, and all of my training; and the generosity of our friends and family to donate to LLS on behalf of Sam (and me), and Sam’s road to full recovery, and my road ahead.

Leading up to the day — including on race morning — I read as much as I could about the “New York Marathon.” All in all, about 70% was inspiring and motivating, and about 30% was terrifying. I didn’t need a writer from the New York Times telling me specifically when I would enter the “pain cave.” I wanted to experience that (if at all) on my own, organically. (Side note: He was right.) But there were enough nuggets and pieces of advice and things to look out for that I felt I would be ready when the gun went off.

As expected, I didn’t sleep much Saturday night. I tossed and turned, listened and read, and then finally gave up. When I actually got out of bed (after reading one last pre-race article), it hit me that this was the day. All of the training, and planning, and travel was but a prologue for what awaited me on this glorious fall Sunday; forget the five months of lead-up, the time was now (well, not really; more about that below). With my race clothes laid out, I methodically went about getting dressed — and layered. Room service delivered my breakfast, which I took to go; I stowed my bags; and I grabbed a cab to Whitehall Terminal.

Upon my arrival at the Staten Island Ferry, I decided to stay ahead of all time curves (good karma, maybe) and took an earlier trip across The Narrows. But note, as this point in time it was still more than three hours before I would run. It was a spectacular day, with bright sun and cool temperatures. I was floored by the sheer number of people (and only half as many as a typical year) who were embarking on this crazy adventure. On Staten Island we boarded buses to take us to Fort Wadsworth. There it was sea of runners bundled up against the cold, stretching, sleeping, eating bagels, and using one of the hundreds of porta potties to deal with pre-race jitters.

My wife had sent me an article about a minyan service held prior to the race, which has been going on for nearly 40 years. This seemed like a very good time to pray. I searched for it and found the Interfaith Tent, which I figured was the right place to be. Unfortunately, everyone was gone. A nice woman (Caitie) told me they did services at 745am and 8am, but they were now over. She offered me a chair (most everyone else was sitting on the grass or cold curbs), so I sat and began reading. I considered eating or napping, or doing something, as I still had more than two hours to go.

Caitie and I got to talking. A mother of two boys, married to a corporate attorney, writing a memoir, she was in from Colorado, about to embark on her second NY Marathon. I peppered her for advice. Soon we were joined by one her friends from grade school, and her friend, and now we had a foursome.

With nothing but time on our hands, we sat and chatted — for almost too long. Before we knew it, it was time to get to our corral, and we needed to hurry before it closed. Caitie and I were in the same corral and in the same wave, so we went over together. Once there, we began the process of shedding our outerwear. You cannot imagine the number of bins filled to the brim with discarded clothing that will ultimately be given to the homeless. My sweatpants, sweatshirt, beanie, and gloves all joined the donation pile before we ever left the corral. Upon our arrival on the edge of the Verrazzano Bridge, with the sun warming us all, I lost one additional layer — something I would come to regret about three hours and 18 miles later.

Caitie and the Author moments before the gun

Masked and huddled, we removed our hats for an inspiring rendition of the national anthem. And then the cannon was fired; and then Frank Sinatra belted out “New York, New York”; and then we were off. It took a beat just to get to the start line, but soon we were moving up the bridge. The conventional wisdom is to go out slow — don’t let your excitement or the energy of the start push you to a pace you cannot keep. The opposite happened for me. My first mile (to the center of the bridge) was super-slow. So slow, in fact, that I knew then — after one mile —that it would be almost impossible to hit the 13.1 pace I had hoped for. But it was going to be a long race, so I didn’t worry about it (at about Mile 3, when Caitie asked, “Are you doing this for time or doing it for fun?,” I knew my answer). Once in south Brooklyn, after just a few turns, the crowds appeared. They started small, with families in front of their houses, and kids on bikes. But once we turned onto 4th Avenue, the party started in earnest.

From Fort Hamilton to Bay Ridge to Sunset Park to Park Slope, the crowds got larger and rowdier. There were so many people, on both sides of the street and on the median, that I figured it would be impossible for me to find my sister who promised to meet me at Mile 8.

It didn’t take too much cajoling to get my sister, now an empty-nester, to fly with me to New York for the weekend. But what I didn’t expect was her plan for race day. She took a cab to Dumbo, rented a Citi Bike, and rode across the Brooklyn Bridge in search of runners, specifically her baby brother. And when I turned onto Lafayette Avenue, just past Mile 8, there she was, holding a fat head with my picture and cheering me on.

My sister & my fat head

I ran past, she got back on her bike, and off we both went. The party in Williamsburg was ridiculous. The runners’ path became extremely narrow as Brooklynites, drunk from brunch, crowded the streets and screamed encouragement. And here the signs on the side of the road got pretty bawdy. Forget “you’ve got this” or “nice legs.” In this part of Brooklyn we got “here to make sure all women finish.” More than once I caught myself saying — to anyone who was within earshot, or just to myself — “this is fucking amazing.” And it was.

Around Mile 10 or 11 I realized my Strava was off, way off. Like half a mile off. Which led me to question all of my training. Was it all a lie? Had I not done the mileage I thought I had? Strava just told me another mile was behind me, but where in G-d’s name is that official mile marker? And so it went for the next two-plus hours. As such, the lady in my ear gave me a half marathon time 2½ minutes faster than the official count (which was still three minutes behind my goal). But I knew at this point that I didn’t have a true rhythm, and that this race was going to be about endurance and survival — not time.

During that stretch, I met a New York area Team in Training coach, who ran with me — and Caitie, for a while — up and over the Pulaski Bridge.

For a few miles, 1986 was forgotten

The next two miles were fine, but at some point either I caught Caitie, or she caught me, and she told me she needed me for the Queensboro Bridge. Truth be told, we needed each other. That thing was a monster. It is a 1.5-mile climb, and both of us were feeling it. But, a FaceTime to her husband and kids (“I love you mommy” does wonders), and an energetic pace runner, helped us reach the peak. And there, at the bottom, was my sister once again.

The Author descending the Queensboro Bridge around Mile 16

We looped around to First Avenue and began the long 3.5-mile straight away. Everyone talked about the roar of the crowd when you get to First Ave., and it was nice and all, but didn’t rock my world. But, it was a party, and I was shocked at how far north we began. In my brain we were going to be in the teens, but we started on 59th Street, and I then realized it would be a LONG time before we were on 59th Street again. The crowds really did help miles 16–19, including the amazing Lesbian & Gay Big Apple Corp. Marching Band around 109th Street, who provided a nice push.

At some point around Mile 9, I essentially tossed out my nutrition regime — it didn’t seem to be working, and I needed more. So, while I ate my first GU at Mile 6 as planned, I supplemented with a banana and multiple orange slices. By the time I got to Mile 18, I just wanted goodness. Throughout Brooklyn and Queens, kids were handing out what I assumed was their Halloween candy. I passed on those early offerings. But now, when a man leaned over the barricade and held out two Reese’s Peanut Butter Cups — well, the allure of those two orange squares was simply too much. I wolfed down the first, and held onto the second. I waited about a mile until I could see a hydration station, then quickly ate the second cup, washing it down with water. I have no idea if it did anything for me physically, but it sure did mentally.

The crowd thinned the farther north we got into Harlem. I looked for my friend Victoria at First Avenue and 125th Street, before I scaled the Willis Avenue Bridge, but I didn’t see her. For me, this is where the “pain cave” began. I walked up to the top of the bridge, and ran down into the Bronx.

Is it any wonder that this is where I entered the “pain cave”?

As expected, there was an incredible Latino vibe in this part of town, with DJs and bands. During one of my training runs, a team member told me how he would drink Pepsi during his Iron Mans. So when I turned onto 135th Street and someone offered me a cup of Coke, I took two. Again, my nutrition plan was totally shot, and I was taking any port in the storm. By the way, it’s always a good idea to wash down Coke with orange slices — at least it is when your body is breaking down after three hours of running.

And here is where I entered the great unknown: Mile 20.

In the pain cave with no idea what awaits

I had never run beyond twenty miles, and I had no idea what was in store. But I did know what I felt like at that moment, and suffice it to say that I was a little scared about what the next hour (hopefully) was going to look/feel like. Fifth Avenue on the Upper East Side of Manhattan is many things — loud, raucous, and welcoming to strangers are rarely on the list. But on Marathon Sunday, it was all of those — and just when you needed it most.

When I came out from around Marcus Garvey Park at 120th Street, I saw my sister one last time. She gave me a bottle of water and words of encouragement, and I told myself, “just get under 100th Street.” Around 95th I started looking for my friend Kelli, and found her with her kids and a large sign with my name.

Friendly faceless on the Upper East Side

She whooped and hollered, we high-fived, and I knew that 72nd Street and The Park were very close.

On the bus ride from the Staten Island Ferry to the staging area, I sat with a man who had run this race a few times. Like with everyone, I asked for advice. Amongst the things he said was, “Once you are in The Park, you are in good shape.” I replied, “But once you’re in The Park, don’t you still have three miles to go?” He said yes, but the people and the closeness to the finish line will get you through.

Well, shortly after Mile 24, while in The Park and amongst “the people” (who, it must be said, were more interested in seeing their friends/family members than actually giving the runners room to, um, run) my right hamstring seized. I felt it about a mile back, but treated it like a rattle in your car, thinking “Did I really hear that? It’s probably nothing.” Then it became something. Time was my enemy, and I felt pretty confident that the miles would outlast the muscle. I was right. So I starting walking. I took huge strides while I rubbed my aching leg. Three guys saw me limping and said, “Come on, you’ve got this.” I defensively and indignantly barked back, “You better fucking believe I’ve got this.” I told myself I would walk until Mile 25. I drank a Gatorade (gross), washed it down with water, and cued up Eminem…

I started running on New Year’s Day, 2004. It began as an excuse to buy an iPod Shuffle. I loaded it with music, and hit the road. Many of the 250 songs on that tiny device were Eminem. His music is propulsive, and really helped in those early months while I was still learning. But for the past few years, I have listened to podcasts while I run (I know, I know). They help keep my mind off the pain and I learn a thing or two.

A few years ago I was finishing a half marathon in San Diego, trying to achieve a PR. The fatigue was kicking in and my legs were getting heavy. So I cued up “Lose Yourself” and gunned it to the finish line. As a I approached the Mile 25 marker, I knew what was needed.

I don’t know how long “Lose Yourself” is, and I doubted it would take me the final 1.2 miles, but no matter. I needed it like a car needs a jump start. When that first note hit (you can hear it now), I took off. I have no idea if I was running a 6-minute mile or a 16-minute mile, but I was going as hard as I possibly could. My hands were air-drumming the beats. My mind was focused on the music and the massive crowd in front of the Plaza Hotel. This was my one shot.

There was a sign: “800 meters to go” which sounded great until I quickly did the math and realized that was still about half a mile. I turned back into The Park knowing the end was near, but not knowing where. The course is a mindfuck; you cannot see the finish line until you are about 200 yards out, and then you see it…up a hill. When I crossed the finish line, I was in a bit of a daze; I could not believe it was really over, that I had finished. I was more tired, and hurt more, than I could ever remember. I was shaken out of my stupor by my phone ringing. My wife had been monitoring my progress and FaceTimed me right after I crossed the finish line. Her smile brought me such comfort; her words eased some of my pain; her planning and encouragement and patience had helped make all of this happen; and so her voice brought me to tears.

IRL/Virtual Finish Lines

She hung up, and we all had to walk. The race planners don’t want you stiffening, so they require you to walk about 100 yards to get your medal; and another 100 yards to get your race bag; and another 100 yards to get your poncho; and then you are required to walk up to 72nd Street to exit The Park and find your way home. There was a blue zombie apocalypse shuffling down Columbus Avenue as we headed south into the waiting arms of our friends and families. I stopped in the ’60s to have someone take a picture, and then I found my sister in Columbus Circle, still with her bike. She rode nearly 30 miles across multiple boroughs to chase me down and cheer me on. We docked the bike and made our way back to the hotel. The journey of more than 50,000 steps was over. An item was checked off the bucket list. And now all that is left are the memories of the moments, and the pain and perseverance and pride. And that is just fine.

As I headed out of The Park, my best friend called to congratulate me. Upon hearing of my pain, he asked incredulously, “Was it an enjoyable experience?” I answered him, in no uncertain terms, “It was magical!”

One final note. I am huge believer in kismet and otherworldly interventions; I don’t really believe in odd coincidences. While searching for the minyan service, I “thought” I found the tent near my starting corral. As I wrote, I missed it completely, and instead found Caitie, who was my friend and my Sherpa for the first 16 miles of this endeavor. I lost her on First Avenue, as she was too fast for me. I never really had a time goal, but going into the race I wanted to be under 4:30. However, at a certain point, I didn’t care and just wanted — needed — to finish. I never got my time; didn’t even look it up.

On Monday morning, Caitie sent me the following text:

From Sam being paralyzed to walking again; from CHLA/Nautica to DC to NY; from the failed minyan to the found friend; from the start in Staten Island to the finish in Manhattan; from an approximate time goal to beating it by less than thirty seconds; from the excitement to the pain; and from the tears of anticipation to the tears of relief and gratitude. Upon reflection one week later, I stand by that original assessment: the New York Marathon was nothing less than magical.

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Dan Freedman

EVP Business & Legal Affairs, Lionsgate. Creator of baseballcraziness.com. Member of @IBWAA. Contributor to “Here’s the Pitch” newsletter. Baseball enthusiast.