The Tampa Bay Ultramarathon taught me about patience, humility and the glory hidden deep inside pain

Show Me Love

click to enlarge Ben Montgomery (L) and Anna Bishop in the midst of the Tampa Bay 100. - Photo by Ben Montgomery
Photo by Ben Montgomery
Ben Montgomery (L) and Anna Bishop in the midst of the Tampa Bay 100.
We were standing in the dark outside the Fort Knox Lounge on Redington Shores, me and Anna and our pain, when a drunk couple spilled from the side door in a waft of smoke, as though the dive bar had exhaled them. The woman glanced over, saw our reflective vests and safety-pinned number bibs, saw our suffering, two pilgrims from Struggleville.

“There must be a walk-a-thon tonight,” she said to her partner.

The word “walk-a-thon” hung in the cool night air. This was well past dark but before last call. The beer bugs danced around the parking-lot lights.

“We ran here,” I said. “From Ybor City.”

“Seriously?” she said.

I mustered a nod.

“Damn,” she said. “Why?”

I’d been asked the same thing—why?—by a half-dozen people since we started the first-ever Tampa Bay 100 with 71 other runners at the J.C. Newman Cigar Factory that morning at 5 a.m., but the answer requires some explaining. I just shrugged. The doors slammed shut on the couple’s car.

Seventeen hours of huffing and puffing teaches brevity. Turns out an ultramarathon can teach a lot of things. Patience. Humility. The glory hidden deep inside pain. The ecstasy of sacrifice. It might even teach love if you let it.
click to enlarge Ben Montgomery quit drinking on Jan. 1, 2023 the same month he turned 45. - Photo by Anna Bishop
Photo by Anna Bishop
Ben Montgomery quit drinking on Jan. 1, 2023 the same month he turned 45.

I quit drinking on Jan. 1, the same month I turned 45. It occurred to me that I might have 30 years left on earth, and I’d spent much of the previous 30 with a drink in hand. There’s something safe about keeping the key to a good time—to social viscosity, to courage, to laughter—in your fist, but I wondered if I really needed it. Or was I hiding behind it?

Three months later, I was fired from a good-paying job in such dramatic fashion that it earned stories in the Washington Post and Vanity Fair, among others, including this publication. The sting made me want to drink; I did not.

I met Anna right after, in April, on a group bicycle ride around Ybor City. My bachelor buddy, always on the prowl, had struck up conversation with her earlier, then introduced us. I feel very awkward in these rare situations, like a punter trying to get rid of the football as fast as possible, but she was beautiful and at ease. She told us she’d come alone because she didn’t have her daughters that night. A few miles later, I noticed she was stopped at a light, texting someone. I braked beside her and just sorta said my phone number out loud.

“8-1-3 …”

She looked up and smiled.

“Put it in your phone,” I said.

“I’ll remember,” she said. Bold.

I didn’t see her for the rest of the ride, but she texted later that night. I’d come to learn that she can’t remember the names of actors or the titles of films, but somehow committed nine numbers to memory on a bicycle ride.

I texted back an introduction and warned her not to Google me because I’d been publicly fired and wanted to avoid some embarrassment. She did anyhow.

“Could I take you on a proper date,” I texted, “or join you for a sunrise run or some such thing?”

“I would be delighted by that,” she wrote back. “What kind of running interests you?”

“The kind beside you.” Send.

I’ve never dated a runner before I met Anna. She’s committed. So serious, in fact, that we’ve been running before sun-up the vast majority of mornings since April. We built a relationship in the soggy soup of summer sunrises, on Tampa’s Riverwalk and Bayshore Boulevard and the Heights. Before long we were running through Ohio’s Hocking Hills in May, then around Vancouver’s Stanley Park in June, then from fort to fort in Old San Juan in July. We did enough running that I began to identify as a runner.

We were running a Flatwoods trail this summer when her friend Mark mentioned the upcoming Tampa Bay 100 Ultramarathon in November, which seemed like a good way to stay on the hook, and fight boredom.

When you stop drinking—and I was a daily drinker for at least two decades—you find yourself with spools of unspent energy and enthusiasm. I should say here that my biological father was a drunk, in addition to being a Southern Baptist Preacher and long-haul trucker. He got my friends and me drunk for the first time when we were 14 or 15. We ran a trotline across a little farm pond called Sandy Curve in Slick, Oklahoma, drank malt liquor and caught catfish, a rite of passage, and we never really stopped. We also worked the next morning, and this instilled in me an important unspoken cultural custom among my people. Drink and work were coupled. Work brought equity that kept us above the bums. It was balance, or penance—like two dogs fighting inside you every day. You have to feed them both or one wins. When you stop feeding them, you find yourself with time and energy that needs a channel.

The dogs quit fighting and started running.

"We did enough running that I began to identify as a runner."

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The course for the Tampa Bay 100 could’ve been a long pub crawl, to be honest. I was aware of this as we ran the length of Ybor’s E 7th Avenue on Nov. 4, past the good-time ghosts. Jason Isbell’s “Traveling Alone” played in my mind:

Damn near strangled by my appetite
Ybor City on a Friday night
Couldn’t even stand up right

When I moved to Tampa in the summer of 2005, a man stabbed another man to death during a brawl in the old Masquerade nightclub, so the Tampa Tribune sent me out to “take the temperature,” as we called it in the newsroom. I drank my way down 7th and came back with a story that celebrated Ybor’s unpredictability. I did another one a few years later for the St. Petersburg Times about a young woman who drank too much at Prana, popped some pills, and stopped breathing a few hours later as four of her also-loaded friends slept around her.

So many ghosts.
So high the street girl wouldn’t take my pay
She said come see me on a better day
She just danced away

We broke free of Ybor City, ran through Channelside and Thunder Alley by Amalie Arena, then up Franklin Street, past The Hub.

“Best dive bar in Tampa,” I said to the strangers running around us.

The last time I was loaded in The Hub, our too-drunk friend slipped away before anyone could get his keys. They found his pickup nose-first in a ditch in Seminole Heights the next day. He somehow made his way—with a broken arm and missing front teeth—to another friend’s house and passed out on the living room carpet. Thank god he didn’t hurt anyone but himself, we all said as we picked up the pieces.
click to enlarge There can be glory hidden deep inside pain. - Photo by Anna Bishop
Photo by Anna Bishop
There can be glory hidden deep inside pain.
Why do we run? I honestly have no idea. I used to walk, and became a bit of an evangelist about it when I was working on a book about one of America’s most-celebrated pedestrians, Grandma Gatewood. All the great thinkers, writers and poets were big walkers—everyone from Dickens to Thoreau to Johann Sebastian Bach. But try finding a great writer who runs.

Sri Chinmoy, a spiritual teacher and athlete who moved from India to the United States in the mid-1960s, argued that running can be a path to enlightenment through self-transcendence, the act of going beyond our prior capacities and limitations. He died in 2007, but every year they still run a 3,100-mile, 52-day race around one block in Queens in his honor.

He taught sobriety, too, something I never thought too deeply about until I started hiking with a Pinellas County lawyer named Bjorn Brunvand. When I met Bjorn in 2018, he was planning to climb Everest to celebrate his own sobriety. Through a turn of events, we found ourselves hiking the Tour du Mont Blanc in 2019. Bjorn told me that he found the path to break free from the herd mentality of America’s booze-obsessed culture in a book called “This Naked Mind,” which argues that lifelong conditioning of the unconscious mind creates in us the desire to drink, and by changing the unconscious mind—Jung’s “the shadow”—we can eliminate that desire.

This is extreme oversimplification, but it piqued my interest in understanding why I felt like alcohol was necessary for me to hang out, have fun, feel right, and sleep.
And it was fuel for a good long run.

"Why do we run? I honestly have no idea."

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We ran south down Bayshore Boulevard as the sun came up over Hillsborough Bay. The Canadian running with us couldn’t stop talking about how beautiful it was. (The next day, I heard he’d dropped out due to extreme dehydration.) We swung north on South Howard and stepped around High Noon empties as workers hosed Friday night’s party off the sidewalks. We ran up and around Raymond James Stadium and I remembered the time I tailgated so hard I slept through a USF game.

The miles came and went and we hit the Courtney Campbell Causeway in stride, past the traditional marathon mark, sun burning hot, then turned north to Safety Harbor and west to Dunedin. At the aid station at mile 50, they told us we were in 12th and 13th place, and Anna was the third female to arrive. She looked pale and her eyes were ringed with salt.

I should probably tell you here, while things are good, how we trained. There was really not much order to it. We ran between five and 10 miles most every morning since mid-April. We built up long runs on the weekends, topping out around 20 miles. I lost about 30 pounds in seven months, and I’m relatively thin to begin with. I flew home to give a lecture in Oklahoma City and my mother asked, in a serious tone, if I was ill.

In retrospect, we should’ve done some strength training because our legs were shot coming over Clearwater Pass. Anna had developed an Achilles pain that forced her to favor her right leg, which prompted pain in her knee. We tried walking some, but that seemed to make our jogging even harder.

The sun disappeared behind the Gulf. We stopped for pizza at Slyce in Indian Rocks Beach and she laughed at me when I hobbled to throw our trash away. Her knee was swelling. Other runners, older runners we hadn’t seen since the starting line, began passing us, gimping along, pacers encouraging them onward.

“You should finish without me,” Anna said when we stopped to sit on a bus bench in Indian Shores. We hadn’t talked in a while, not since she snapped shut my pep talk at the pizza place a few miles back.

I thought about running the next 30 alone, what that would take. Ache had fully inhabited my legs. I’d lost a toenail. But I was pretty sure I could make it. I was more certain that I was here because of the woman sitting beside me, who had run 69 miles to get here.

If you saw two bedraggled people gimping southbound on the shoulder of Gulf Boulevard around 10 p.m. on Nov. 4, hand-in-hand, after 17 hours of running, just know that they gave the Tampa Bay 100 their best effort.

Anna closed her eyes on the Uber ride home and I watched the streetlights race across her forehead. I helped her inside her house and she collapsed on the bed and I slipped the Nikes off her feet.

I’d learn in the days ahead that 49 runners finished the 100, and 23 didn’t. DNF, they call it—Did Not Finish. In my mind’s eye, I caught an Uber back out to the Fort Knox Lounge and coaxed my legs into moving again. I ran the last 30 miles and crossed the finish line on the beach at Vinoy Park, then climbed back into bed beside Anna and fell asleep, happy.

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