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Alcatraz, My Alcatraz: Taking On The San Francisco Bay Swim

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The cold-water swim in the San Francisco Bay is a notorious one. With the 30th Escape From Alcatraz Triathlon set to take place this Sunday, May 2, Joe Oakes takes a look at two swimming fanatics who have battled the waters more than a hundred times to earn the title of Alcatraz Centurion.

Written by: Joe Oakes

Bobby Roper was gazing out the picture window in the South End Club’s dayroom, watching a huge tanker as it glided behind Alcatraz Island, heading up San Francisco Bay to the Chevron refinery in Richmond, when he noticed that one of the Zodiacs (rigid-hull inflatable boats) was being readied for launch on the pier below him. “Oh, shit,” he said. There goes another one!” He turned away and snatched up a newspaper and a cup of coffee and plunked himself down on the sofa.

Roper, a retired California marshall, is a San Francisco swimming legend. In his time he set speed records for swimming from Alcatraz to San Francisco and across the Golden Gate Bridge. He was a member of the relay team that swam 26 terrifying miles from the Farallon Islands, the western corner of the great white shark’s “bloody triangle,” to San Francisco. The feat has never been repeated. But this morning he was turning his attention away from the people readying the Zodiac on the South End pier below him. He turned to Wayne Black and asked, “Is it the Little Mexican or Emich this time?”

The “Little Mexican,” Pedro Ordenes, is actually a Chilean, and swimming in cold water is in his blood. He grew up in Punta Arenas, Chile, on the shore of the Strait of Magellan, the next step north of the Antarctic Peninsula. There is a rumor that Ordenes freezes his oatmeal into popsicles for breakfast.

Gary Emich is an escaped Florida beach boy, a USAT-certified swimming coach and a retired post office official. Here is the thing about these two guys: They have each swum from Alcatraz more than 600 times, and they are locked in a duel to the death to see who will end up with the most Alcatraz swims ever before meeting the Grim Reaper.

Photo: Kurt Hoy
Photo: Kurt Hoy

A few years ago I was present at a special swim when both Emich and Ordenes did what had never before been done: They completed their 100th Alcatraz crossings, and they did it together. To honor them, a new term was coined: “Alcatraz centurion.” They were partners in their glory and both knew that there would be more Alcatraz swims to come. Then something happened—their partnership turned into a race to determine “the baddest ass on Alcatraz.” Ordenes, a loquacious Latino who is a little older (both are in their 60s), suddenly became evasive whenever he was asked about his current total as the numbers mounted up. Emich, a cool customer used to dealing with postal Postals, responded by tweaking up the pressure. They were locked in what was becoming an unending and unbending battle: swim or die, or maybe both.

People started taking sides, and betting money might have changed hands. There were accusations that one of them was using swim fins, a definite no-no in an old-school atmosphere where wetsuits are still called wuss suits: “If you are wearing fins, you are not swimming; if you are wearing a wetsuit, you are floating.” Whenever one went out of town for a few days, the other would cram in as many Alcatraz swims as he could. Emich did five one day.

And they kept piling on the numbers—200, 300 and now 600. They were building reputations as studs and reaping the benefits. Emich, who is super-organized, got himself certified as a USAT swim coach, put on seminars and travelled internationally for Swim Trek, a British swim-tour company. Ordenes, a little more on the loosey-goosey side, stayed closer to home, started a low-key swim company that customizes swims from Alcatraz for small groups. His website said that he was a world record holder, but it did not elaborate. In truth, while both men are both good swimmers, neither of them comes close to being world class. (The big difference between the two of them is Emich’s supportive, intelligent wife, Peg, who tries hard and unsuccessfully to keep him on the straight and narrow. Ordenes’s family is in Miami and Chile.)

Roper walked away from the window, not wanting to witness one more swim in a seemingly infinite series of more of the same. “Bobby, it’s neither of them this time,” Black said. “I think it’s the Kid, Stevie Ray,” and Roper smiled.

Emich and Ordenes are hearing footsteps these days. There are a dozen younger, faster swimmers, all members of the South End Club, coming up fast behind them, and all well past the 100 mark. Stevie Ray is leading the chase pack, but there are others, such as Christine “Bucko” Buckley. A few years ago Buckley was swimming across the English Channel when a storm came up, buffeting her with gale-force winds and big waves. Her pilot advised her to come out of the water, and Buckley gave him a Bronx cheer, going on to finish her swim in a very difficult 17 hours. The English Channel Swimming Assn. named Bucko its inspirational swimmer of the year. For Emich, Ordenes, Ray, Bucko and the rest, Alcatraz has become an addiction, bordering on a religion.

How does it happen that they can pile up such big numbers when most people have to wait in line to get in just one Alcatraz swim a year? The answer is simple: They all belong to the South End Club. Instead of getting a normal night’s sleep, they are up at 4 a.m., at the club at 5, in the water before 6 and at work at 8. All they need to do is reserve a club boat and find a pilot to ferry them out to Alcatraz and guide them back. There isn’t a swim club in America that is more supportive of the ambitions of its rough-water swimmers; more South Enders have crossed the English Channel than any club outside of England.

These kinds of things don’t just happen. Someone has to create an atmosphere to make them happen, and the person who has had the greatest influence over the years is none other than Bobby Roper. He is the official guru of the Sunrisers, an unruly gang of South End swimmers who take pleasure in engaging in daily early-morning aquatic combat with ferries and the Coast Guard. And even though Roper may scoff at the centurions piling on numbers, his heart is as big as the bay, exceeded only by his enthusiasm for swimming.

But where did the obsession with Alcatraz come from? Blame me. Mea maxima culpa. Since the founding of the South End Club and its neighboring Dolphin Club in the 1870s, the two clubs held a monopoly on swimming from Alcatraz. Outsiders were not invited, and there were maybe 100 people making a crossing each year. In 1981, after my fun day of slogging through the Ironman in Honolulu, I said to myself, “Hey, we’ve got to do something like that in San Francisco, but not as long and boring, and a lot more intense. It will start with a very cold swim from Alcatraz and finish with a run across the mountainous and notoriously hot Dipsea Trail—twice. I will connect it up with a bike ride across the Golden Gate Bridge.” Thus was born one of the very first triathlons on mainland U.S. soil. It started as a club event, and so it remains, but it has bifurcated and been copied into a variety of competing events—triathlons, swim-run events and just plain swims.

So, yeah, blame me. Over the years I have earned a few bucks (not many) and learned a few hard lessons. As of now, more than 20,000 swimmers have gazed up at my smiling face as my Team Alcatraz has guided them across those cold and roiling waters. But after almost 30 years, I’m getting ready to cash in my chips and walk away. Anyone want the job?

And, yes, we have had to yank more than a thousand swimmers from the water, some of them excellent swimmers who got in a little … ugh … over their heads. Nobody ever said it would be easy. If you are a mere mortal and not a centurion, approach with caution.

Now, if you have your eye on breaking that most-swims record, you are already more than 600 swims behind, but you have the rest of your life to catch up. Why not? Just call Bobby Roper or me for some quick advice.