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Trial by Water

Could this 57-year-old meet his ultimate challenge: swimming the frigid waters from Alcatraz to the San Francisco shore?

Two years before my father died, he and I swam together. He was 79, and though weakened by age, and recovering from a stroke, Dad churned through the water, slow but steady, like a steamboat on the Mississippi. He was always an expert swimmer and graceful diver, and he had insisted that all seven of his children learn to swim at an early age. I competed—happily, despite mediocre results— until I was 12 or so, but my most pleasurable aquatic experiences took place well beyond the confines of pools. I’ve never been able to resist the allure of open water, plunging gleefully, sometimes recklessly, into rivers, lakes, and seas everywhere I’ve traveled.

As the years passed, the more I appreciated my father’s prescient gift, though it took on special meaning when I turned 40. My life had devolved into a sedentary routine. I commuted to work by train, a monotonous trip lasting an hour and a half each way, and five years of such cattle-car coming and going had saddled me with excess weight. Reversing my decline, I knew, would be an exercise in self- induced misery. Choose something you enjoy, the fitness gurus always advise, because that increases your chances of weathering the hellish first stage of physical redemption. So I did. I returned to the pool.

What a sobering day that was, that first day, when swimming a mere ten laps exhausted my much depleted resources. Keeping me going was a mixture of blind hope (Eventually this will be fun), newfound fear (If I don’t do this now, soon I won’t be able to do anything), and anger at myself (You idiot, how could you let this happen?). I wish I could report that swimming instantly became an undiluted joy, but it took months. Progress was painfully incremental. Lapses were numerous and came with discouraging setbacks. Yet gradually, one lap at a time, one workout at a time, I lengthened my swims. Then I focused on increasing speed. I lost more than 30 pounds. I firmed up, felt younger, more energetic. Three years on, I was swimming two miles, five days a week. And I was having fun, great fun. I’d converted my agony into a gratifying addiction.

Many of the 517 swimmers were serious athletes. Oh, man, I thought—I’m out of my league.

With the renewed vigor came a growing desire to test myself in open water, the ocean especially, which I indulged every time I left my home in southwestern Montana for a seaside locale. A few years ago, during an offhand moment while teaching at the UC Berkeley Graduate School of Journalism, I found myself waxing enthusiastically about sea swimming. A student suggested that I try one of the organized events in San Francisco Bay, perhaps an Alcatraz crossing. I laughed it off, thinking that such a feat was beyond the capabilities of my fiftysomething body. But every time I drove over the Bay Bridge or Golden Gate Bridge, or walked the steep, seaward streets of the city, my gaze was drawn to the island, then to the rough, churning reach that separated it from the waterfront.

And I wondered: Was crossing that actually possible?

One of the reasons I enjoy swimming is the exquisite embrace of total immersion. That’s why I don’t wear a wetsuit. That’s also why step one in my Alcatraz quest was simply seeing if I could endure the notoriously cold water of San Francisco Bay. In 2006, when I was back in the Bay Area, a new friend, Kate, invited me to join her at Aquatic Park, a public swimming area on the San Francisco waterfront. On an overcast fall morning, I went for my inaugural swim, wearing only a Speedo and a cap.

Public pools are typically kept between 80 and 85 degrees, while lap pools range from 75 to 80. The water here was 57 degrees, with patches even chillier. Had I lingered a few seconds where the water was shin-deep, my ankles would have gone numb. So I kept walking. The cold advanced up my legs, over my knees, convincing me that an all-at-once shock would be better than prolonging my entry any longer. I dove headfirst. My chest tightened, my temples ached, I gasped for breath. It seemed as if my entire body was about to shut down. Then raw instinct took over. I swam a couple of strokes, reversed direction, swam back, left the water, and ran back in, repeating the process several times until the cold lost some of its sting. When I was ready, I turned to my much more experienced partner: “Okay, Kate. Let’s go.” We plunged in together. And this time I kept going.

Remember this day, I said to myself. Hold on to it. I was cold, yes, but also electrically alive. We swam parallel to shore, and after a few minutes I passed over the threshold that all sea swimmers come to know, and trust, when the warmth one generates internally becomes the equal of the surrounding water, or so it seems, and seeming so is enough.

As Kate and I warmed up in the saunas at the Dolphin Club, which shares a building with the South End Rowing Club at Aquatic Park, I could scarcely contain my joy. It was as if I’d discovered a new country, one I was eager to explore. With my skin still tingling, I decided: I would attempt a crossing. I was 56 years old, in fairly good condition, though surely no gonzo athlete, and surely not without doubt. But I had to try it. I would make the attempt during the next Alcatraz Invitational, a swimming event that South End holds every year in the raw, dark waters of San Francisco Bay.

During the two weeks before I returned to Montana, I continued to swim at Aquatic Park. And during each workout, I paused in the outlet separating the relatively calm lagoon from aqua incognita beyond. There, alone in the water, I gazed at Alcatraz. The crossing would be 1.25 to 1.5 miles, depending on the currents, but the island and its notorious federal penitentiary seemed much farther away. I shuddered, then worked my arms and legs faster to fight off the encroaching chill. It was easy to imagine being paralyzed and disoriented by the icy water and daunting currents. The inmates were told that the bay swarms with man-eating sharks, a lie that discouraged everyone but the most daring from attempting escape. The cold and the danger occupied my thoughts as I studied Alcatraz. *How strong will the currents be on the day of the race? What about the chop? Will I be tossed about like a cork? Okay, the sharks are harmless bottom feeders, but who really knows what will be eyeing me from below?*

Even without the lore, Alcatraz remains forbidding, by virtue of its physical presence alone—a cluster of brooding buildings anchored to a platform of solid rock. Sometimes enshrouded in fog, other times lit up by the sun, the island shifts mood from hour to hour. It can look like a majestic ship plowing across the bay, a castle floating eerily above the water, or a deserted, ominous outpost of wrecked ambition.

The feeling in the tips of my fingers was ebbing away, telling me that I needed to resume swimming. I turned away from Alcatraz and swam back toward shore, arm over arm, pulling harder as I went, now more appreciative than ever of the challenge that would await me upon my return, a year later, on September 15, 2007.

To make the swim as real as possible, I signed up shortly after I returned home. I also told everyone, friends and family alike, what I intended to do. That would make it harder, I reasoned, to back out. For inspiration, my daughter, an artist, sent me a painting of the bay, which I hung on the wall where I work. On the back she’d written: “Happy Birthday to Aquapapa!”

From November 2006 onward, I trained in the 25-yard indoor pool at the local YMCA. I wasn’t as consistent as I would’ve preferred. Nor was I willing to give up certain vices—least of all, my taste for whiskey. But slowly I improved my endurance, and by June, I could swim three miles at a respectable pace—about 30 minutes per mile. With summer came open-water opportunities, mostly in lakes, which aided my reacclimation to cold water. Then, ten days before the event, I completed my training with four hourlong sessions in Aquatic Park and a side trip to accompany veteran distance swimmers off Santa Barbara.

I had trained well, and that’s what I told myself, but the mantra did little to calm my nerves the morning I arrived at Aquatic Park for the swim. Swimmers, many of them clearly serious athletes, were already lined up at the registration tables. Oh, man, I thought—I’m out of my league. In the predawn darkness Alcatraz was indiscernible save for the skylights above the main cellblock, partially illuminated by the island lighthouse. Throughout all that followed—signing in, strapping a timing-chip band around my ankle—I kept an eye seaward. Slowly, as sunlight spread across the bay, Alcatraz emerged from the blackness, was enveloped by the fog, reemerged, then disappeared again, which reinforced its remoteness. The cove was placid, but on the other side of the outlet a breeze was up and the water had already begun to churn. I was nervous. But uncertainty, I reminded myself, is one of the charms of sea swimming.

My interior pep talk was halted when the race director told us to walk six blocks eastward, to Pier 41, where a ferry waited. More than 500 of us marched down Jefferson Street. Traffic stopped. Tourists snapped pictures. Adding to the festive atmosphere was a bagpiper who led our merry band of swimsters to our fateful embarkation. Never mind that I associate bagpipers with funerals.

A different drama unfolded while the ferry motored to Alcatraz. All of us huddled together in a large room on the first deck. Merriment gave way to sober anticipation. Some stretched; others adjusted goggles. The excitement was palpable. So was the warmth of hundreds of bodies—bodies, I now noticed, of every kind: tall and short; skinny, chubby, and ripped; wrinkled and youthful. It was reassuring to see dozens of swimmers in their 50s and 60s. Over the loudspeaker came an announcement: we had reached Alcatraz. The ferry slowed to a stop. My nervousness was full-blown. Can I do this? I can do this. Can I do this? My heart hammering against my ribs, I threaded through the crowd for a better view. The Rock—the reason for the nickname was clear—filled the entire side window, hard and unforgiving. Doors on both sides of the boat opened. Swimmers shuffled forward and, three at a time, dropped feet-first into the water, ten feet below. After a wait that seemed both fleeting and endless, my turn came. I stepped to the edge, almost mad with adrenaline. Someone behind us yelled “Go!”

I jumped.

The water temperature was 63 degrees, frigid by most standards but balmy for San Francisco Bay. Yet when I hit the water, sinking a couple feet below the surface, I was stunned. The effect came not only from being seized by the cold, but experiencing, in silence and with unparalleled immediacy, the very wildness of the bay—the depths, the overwhelming power, the scary-yet-inviting aliveness. Whatever happens, I realized, will be on the sea’s terms, not mine. My survival depends on bending to its will.

I resurfaced amid a frenzy of thrashing bodies and two-foot waves. Get moving. Now. I swam through the roiling water, straining to look toward shore. Salt water poured into my mouth, the dull metallic taste reminding me to relax, to conserve my energy. Calm down, Ed. Find your rhythm. As my excitement subsided and I smoothed out my stroke, I fell into a cadence that felt right. Soon I crossed the magical, merciful temperature threshold; the water no longer pained me. I looked up to get my bearings. We’d been told to use an apartment building on the hill above Aquatic Park as a landmark. But it wasn’t visible. Nor was much of anything on the waterfront. I panicked. I can’t see where I’m supposed to go. Then I spotted the safety kayaks escorting us on both sides, and I steered a course straight down the middle.

Whatever happens will be on the sea’s terms, not mine. My survival depends on bending to its will.

The race was scheduled right before slack tide, meaning the currents would be mild. Swimmers were spread out in all directions, making collisions less likely. Waves jostled me from side to side, but they were fairly small, and—as advised by Kate—I adjusted my rhythm to roll with them. To my left, a young woman stopped to snap a photo of San Francisco with a camera she had tucked into her suit. I, too, took in the view: Golden Gate Bridge, the city skyline, the Bay Bridge. What would Dad think of this?

I now could see the landmark building, the piers below, maybe a third of a mile away. My arms were weary, but I didn’t slow down. A current became noticeable, pushing me westward. The outgoing tide. Several times I was forced to adjust course, re-aiming for Aquatic Park. It dawned on me that the experience would soon be over. Pay attention to every detail. I passed through another cold spot, which shocked me to the core. A breeze tickled my shoulders. Bubbles of exhaled air rolled across my cheeks. When the sun emerged briefly from the mist, the surface of the water spangled, then went green-black again. Every time I turned my head, I stretched my hand toward the sky and breathed in the delicious salt air. And every time I plunged my arm back into the water, I reached toward the darkness below. This is exactly where I want to be.

Two hundred yards from Aquatic Park, I found myself in a frenetic crowd again. The swimmers who had strayed to the sides now funneled through the opening to the cove. I slowed, veering this way and that, finally making it to the calm waters on the other side. A crowd had gathered near the finish line, and seeing them spurred me on. I felt powerful. But when I arrived in the shallows and tried to stand up, I realized that the last-minute burst of energy was due more to temporary exhilaration than any hidden reserves of strength. I faltered, then paused to steady myself. My legs felt rubbery. I slogged through the water, now three feet deep, then hobbled as best I could. I wanted to make a good showing as I crossed the finish line.

Awaiting me on the beach was a ravishing mermaid—my girlfriend, Seonaid, in costume—holding a flask of single-malt Scotch. Like the proverbial call of the Sirens, being welcomed by a sea-born beauty and sipping Lagavulin was irresistible to this old sea beast. As Seonaid and I stood together on the sand, gazing back toward Alcatraz and the water I’d just crossed, I was already looking beyond that place, that day, to other sea swims. The satisfaction of having done what I set out to do was far more intoxicating than the whiskey. I was ready to plunge back in.

A Harper’s Magazine contributing editor, Edwin Dobb is back in the pool, training for next season. For info on the swim, call 415-776-7372 or go to

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