Inside the High Tech Hunt for a Missing Silicon Valley Legend

The news that Gray was missing shocked the high tech community. The lanky coder had been a computing legend since the 1970s. His work helped make possible such mainstays of modern life as cash machines, ecommerce, online ticketing, and deep databases like Google.

The Gulf of the Farallones, 2007
Photograph by Todd HidoIt looked like a fine day for a sail. On Sunday, January 28, 2007, Microsoft researcher Jim Gray woke up on his boat, a red 40-foot fiberglass cruiser called Tenacious. The water in Gashouse Cove, a cozy marina in San Francisco Bay, was nearly flat. The 63-year-old programmer phoned his wife, Donna Carnes, who was on an annual vacation with friends in Wisconsin. He said he was heading out to the Farallon Islands, a wildlife refuge 27 miles offshore, to scatter the ashes of his mother, Ann, who died in October.

As Gray steered out through the Golden Gate to the open ocean, both tide and wind were in his favor. At 10:30 am, he called Carnes again and said that he was approaching a channel marker buoy 15 miles out. She asked him if he was wearing his harness; single-handed sailors can drown if a wave pitches them overboard and the ship sails on. "Yes, dear," he replied, saying that he would get in touch as soon as Tenacious came back into range.

A few minutes later, he left an upbeat voicemail for his daughter, Heather, in Santa Barbara. "I’m taking Granny out to her final resting place. I’m surrounded by dolphins out here. It’s a little cloudy but very pleasant. No whales but lots of dolphins and very pretty. Love and kisses, take care, bye." At 11:50 am, his smartphone synched with Microsoft’s email server one last time, pinging a Cingular tower south of San Francisco. A couple of hours later, on Southeast Farallon Island, a naturalist named Brett Hartl spotted a sailboat with a reddish hull a mile or two offshore, sailing north.

Then Gray and his boat vanished. The Coast Guard received no Mayday call, and Gray’s EPIRB — an emergency radio beacon designed to broadcast a homing signal if it sinks — stayed silent. No sailors in the area reported seeing the boat adrift, and not a single life vest, flashlight, or scrap of debris belonging to Tenacious washed up on local beaches.

Jim Gray aboard Tenacious in 1996. He and his wife Donna were both avid sailors who periodically lived on their boat on the San Francisco Bay.
Courtesy Joel BartlettThe news that Gray was missing shocked the high tech community. The lanky coder had been a computing legend since the 1970s. His work helped make possible such mainstays of modern life as cash machines, ecommerce, online ticketing, and deep databases like Google. "Jim’s work inspired us and many other computer scientists to seek out and tackle very ambitious projects," says Google cofounder Sergey Brin. "He never shied away from problems involving large-scale data and computation."

When Gray joined Microsoft in 1995, he convinced the software behemoth to launch a research center in San Francisco so that he and his wife wouldn’t have to move to Redmond. "If Jim had wanted a lab in Monte Carlo, we would have built a lab in Monte Carlo," says Microsoft Research chief Rick Rashid. In 1998, Gray’s peers gave him the highest honor in computer science, the A.M. Turing Award.

His influence reached far beyond the insular world of coding and computers. Each morning, as Gray strolled down to the lab from his rustic Victorian on Telegraph Hill, he chatted on his cell with one of the many scientists who became regular guests on his boat. He could talk to astronomers, oceanographers, geologists, geneticists, or fellow programmers and seem like a native in each field. And he felt equally comfortable hiking along the Tahoe Rim Trail or sailing up the Sacramento River delta with his wife.

Gray’s mysterious disappearance inspired one of the most ambitious search-and-rescue missions in history. First the Coast Guard scoured 132,000 square miles of ocean. Then a team of scientists and Silicon Valley power players turned the eyes of the global network onto the Pacific. They steered satellites and NASA planes over the Golden Gate and mobilized the search for Tenacious on blogs and on Amazon.com. This group included some of the best minds in science and technology, among them Amazon.com chief technologist Werner Vogels and top executives at Microsoft and Oracle, including Bill Gates and Larry Ellison. Oceanographers and engineers from the US Navy, NASA’s Jet Propulsion Lab, and the Monterey Bay Aquarium Research Institute joined the effort, as did astronomers from leading universities.

The search became national news and gripped the imagination of the blogosphere. Some commentators tried to cast the programmer as a digital-age D. B. Cooper, who disappeared in 1971 with a suitcase full of cash by leaping from the back of an airplane — though Gray had no evident motive to flee.

During the search, Carnes stayed in seclusion with a security guard posted at her door, refusing to talk to the press. But as salvage boats and remotely operated underwater vehicles scanned the seafloor along California’s north coast, she met with me in the house she shared with Gray. "I am determined to find out what happened to my husband," she said. "And I am determined to find Tenacious, because she is the key to Jim, and to this strange, singular, very painful mystery."

Carnes spent the last normal afternoon of her life skiing near a remote lakeside lodge in northern Wisconsin. On Sunday night, concerned that she hadn’t heard back from her husband, she phoned the harbormaster at Gashouse Cove, who verified that Tenacious’ berth was still empty. Then the harbormaster called the Coast Guard.

When David Swatland’s phone rang at his Berkeley home that night, he hoped it would turn out to be a routine case of an overdue sailboat with the usual happy ending. The deputy commander of the busiest Coast Guard sector on the West Coast, Swatland and his team fielded 1,705 search-and-rescue calls in 2005 alone. Most were relatively minor — drifting kayaks or hikers stranded by the tide. A former triathlete with a reassuring manner, Swatland says he gets several reports a week of boats late coming home from the bay, but they usually turn up in a marina somewhere within a couple of hours. He gets fewer than 10 calls a year about boats gone astray in the ocean, though these cases too are usually solved in a day.

"Most sailors are pretty careful outside the Golden Gate, because they’re aware that this is a particularly unforgiving stretch of coastline in a particularly unforgiving ocean," Swatland says. "There are only a few good anchorages, it’s often windy, and there’s a fair amount of boat traffic. Things can get squirrely out there."

The Coast Guard, which became an arm of the Department of Homeland Security in 2003, keeps watch on the San Francisco sector from a command center on Yerba Buena Island, under the Bay Bridge. After the harbormaster’s call, Swatland’s crew broadcast a description of the black-masted sailboat to mariners. Later that night, an 87-foot patrol boat roared out from the command center, joined by a motor lifeboat capable of handling a 360-degree roll in the surf. By 1 am, a helicopter and a C-130 turboprop plane, both equipped with thermal-imaging radar, began flying tight grids out to the Farallon Islands. Carnes stayed up all night, getting updates every half hour.

In the morning, the Coast Guard sent out its standard press release about a missing sailor. Swatland was unaware that Gray was well known in tech circles until local news reporters made the Microsoft connection and descended on Yerba Buena Island with TV cameras. The news spread quickly among the programmer’s colleagues and friends.

On Monday night Paula Hawthorn, a former VP at Informix who had known Gray for 35 years, got a call from her son Andrew. He reminded her of how helpful Carnes had been when Hawthorn’s own father was dying of cancer. "You have technical and organizational expertise, and you ought to be helping Donna," he told her. Hawthorn lay awake most of the night, thinking of ways that Gray’s illustrious friends — with their connections to major scientific institutions and three-letter agencies in Washington — could assist the search. The next day she sent an email to a core group of his associates suggesting the use of satellite imagery to supplement the Coast Guard’s boats and planes. (The commercial satellite industry got an early boost from a Web site called TerraServer, one of Gray’s first projects at Microsoft, which made high-resolution imagery of the planet available online seven years before Google Earth.) "Does this sound possible, helpful?" she wrote. "Who do we need to talk to?"

It was the kind of gutsy idea Gray might have come up with himself. Hawthorn’s email was forwarded to Sergey Brin, who promised to talk with satellite company DigitalGlobe, Google’s primary image provider. More feelers went out from the group to other satellite vendors. The ever-widening CC list christened itself the Friends of Jim.

By midweek, Swatland was assigning more Coast Guard boats, helicopters, and personnel to the search. He brought in local sheriff’s departments and the National Park Service to patrol the coastline, and ran computer simulations to predict where Tenacious might be drifting if its skipper had suffered a heart attack or other catastrophic event.

Meanwhile, Joe Hellerstein, a former protégé of Gray’s who had become a computer science professor at UC Berkeley, launched a blog to coordinate the online effort. Gray’s Microsoft colleagues worked with the Coast Guard to bring more technical resources to bear on the search. "Sometimes I felt a little self-conscious because they were all smarter than I was," Swatland says. "They had connections to stuff I’d never heard of."

This emergency mobilization gave many in the Bay Area tech community déjà vu. In late November 2006, CNET editor James Kim and his family had become stranded in the Oregon mountains. Kim’s wife and children were saved because two Edge Wireless engineers spent hours examining phone logs, finally spotting a cell-tower ping that helped a rescue pilot locate them just in time. But Kim, who had gone looking for help, was found dead two days later.

Determined not to let history repeat itself, the Coast Guard asked Cingular for Gray’s complete cell phone records so it could triangulate his last point of contact. At first the company balked, citing privacy concerns. "Cingular was hesitant to give us all the information we were looking for. They seemed skeptical about the Coast Guard being a law enforcement agency," Swatland says drily. Eventually, the company coughed up the data.

At least the weather was cooperating — the sky was crystalline, and the seas were unusually calm for that time of year. Search pilots could see beer coolers and other flotsam bobbing in the water below. But none of it belonged to Tenacious.

As the search area expanded, the Coast Guard had to consider the possibility that Gray didn’t want to be found. Rumors flew around docks and online sailing forums that the "wily maverick" programmer might be recklessly crossing the Pacific or "already settling down to a round of margaritas in Baja," as a reporter for the San Francisco Chronicle put it. "We had to weigh all the scenarios, including ’I want to escape,’ as uncomfortable as that was to mention to Donna," Swatland says. "But guys who try to disappear usually have financial issues, legal issues, or they’re in the middle of a divorce. Jim had nothing like that."

There was also a darker possibility to consider. Gray’s mother’s death in October followed the unexpected death of Carnes’ father, Don, in June. Watching Ann lose her ability to walk before dying of old age at 97, Jim confided to Donna, "I have seen my future, and it is ugly." Could Gray’s grief over his mother’s death have caused him to scuttle his own boat?

Friends who spoke to Gray nearly every day find this scenario unlikely. By all accounts he was content in his marriage, committed to his work, and delighted with the arrival of Sam, his first grandchild, born in 2005 to Heather, his 38-year-old daughter from a previous marriage. "My dad was happier than I’ve ever seen him," Heather says. "He was always so successful, and balancing that with his personal life was a challenge. But he had finally struck that balance."

As days passed, Swatland felt increasingly frustrated. "I couldn’t figure out what had happened to this guy," he says, "unless he was kidnapped by Apple."

Any tech company would have been eager to get its hands on Gray. He had managed to stay at the leading edge of computer science for decades, and his résumé reads like a timeline of key developments in the digital age.

Born in San Francisco in 1944, Gray spent his first years in Rome, where his father, James, was a spy for the US Army. After his parents separated, Gray and his sister, Gail, returned to the Bay Area to be raised by their mother. James went off to become an inventor, making a small fortune by patenting an early typewriter-ribbon cartridge, while Ann taught English in public school.

On frequent visits to the aquarium and planetarium in Golden Gate Park, Gray became fascinated with science. As a gangly teenager, he devoured books like Norbert Wiener’s The Human Use of Human Beings, which made the bold prediction that computers would someday be smart enough to play chess and tackle social problems. Gray got another kind of education on camping trips with his uncle to Yosemite, where he learned the thrill of surviving in the woods with minimal gear. Gail says that her brother became "a bit of a daredevil" as he got older, "taking chances because he always thought he could do what he set out to." When the family spent days at the beach in Santa Cruz, he would swim alone out past the breakwater.

Gray enrolled at UC Berkeley in 1961, grew his hair long, and rented a basement room with a dirt floor for $5 a month. He thought about majoring in philosophy but lost interest when he discovered computers. He signed up for graduate classes without taking the prerequisites, and in 1969, he earned the university’s first PhD in computer science.

After a stint at Bell Labs, the scruffy young coder took a job with IBM Research in San Jose. He gamely plunged into the nuts and bolts of data management, considered a dreary backwater even by avid readers of the Systems Journal. Back then, inputting a request to a data bank (the word database hadn’t caught on yet) required a thicket of query syntax and a team of programmers. But in 1969, an IBM mathematician named Ted Codd had an epiphany. He sketched out a model for a so-called relational data bank that would make it easier to sift relevant needles from haystacks of information.

Gray joined an R&D team that was attempting to turn these theories into functioning software. His work focused on transactions: When should changes be firmly committed to the database? What if one of a pair of transactions fails halfway through? How can two (or 2,000) users access the same data simultaneously without corrupting it? In his research papers, he compared transactions to a marriage contract: What was the right moment to say "I do"?

Gray’s solutions to these riddles are now embedded throughout the networked world, from Amazon.com to the corner ATM. The data bank he created with his colleagues, called System R, laid the technical foundations for a new industry. Updates of its query language, SQL, are still widely used. Compared to their clunky predecessors, relational databases turned out to be better suited to the revolution just over the horizon — GUIs, parallel processing, and the Web.

System R also inspired a seminal open source project at UC Berkeley, a relational database called Ingres, built by a crew led by Mike Stonebraker, now a professor at MIT. Though the teams at IBM and Berkeley were officially competing for the same small market, Stonebraker recalls, "Jim was unbelievably smart and very willing to help without getting credit. Most people considered business data-processing to be beneath them. Who would help Bank of America cash checks? No one foresaw how essential databases would become."

No one but an aspiring entrepreneur named Larry Ellison, then a young programmer working at Ampex on a data-storage scheme for the CIA. The agency’s codename for the project: Oracle.

In 1977, Ellison launched a startup called Software Development Laboratories, using System R’s papers as the blueprint for his own software. Then he repositioned his database for the emerging minicomputer market, betting that Big Blue would drag its heels. Ellison bet right, and the rest is Silicon Valley history.

"There was no love lost between Jim Gray and Larry Ellison. They hated each other," one of Gray’s Microsoft colleagues says. But Gray was gracious in public, and he mellowed with the years. He told an interviewer in 2005 that his life had been a "researcher’s dream — you have a lot of fun, you do something innovative, and then people make billions of dollars off of it."

And Gray never stopped innovating. At Tandem Computers and then Digital Equipment Corporation in the ’80s and ’90s, Gray helped develop what is now called grid computing, paving the way for the mammoth server farms that made big-iron mainframes obsolete. Though he felt more at home in industry, Gray would accept the occasional academic chair or fellowship. This gave him the chance to nourish the careers of promising upstarts like Amazon’s Werner Vogels, who asked the programmer to sit on his doctoral committee at the Free University of Amsterdam. Long before Google appeared on Redmond’s radar, Gray was advising Sergey Brin in Mountain View. Asked which of his achievements made him most proud, Gray once said, "The people that I’ve mentored."

"Jim was extremely forward-looking and had very few boundaries in his mind," Vogels says. "When Jeff Bezos wanted to hire me, he was the first person I called to ask what to do. When a question came up in my research, I’d shoot Jim an email. He was the ideal person to use as a soundboard for ideas."

Along the way, Gray got married and divorced twice, raising Heather with his first wife, Loretta. In 1984, he met Carnes, an articulate Norwegian-American beauty with master’s degrees in history and education. An avid sailor and hiker, she accepted his proposal on their third date — on his boat, of course. She became an engineering manager in the Valley, and they spent their vacations sailing and reading Tolkien aloud to each other in the wilderness. When they bought the house on Telegraph Hill, they christened their nautically themed bedroom Gondor — the realm of the Ship-Kings.

Courtesy Joel Bartlett"I fell head over heels in love," Carnes says. "We’d both been married before, but we met our match in each other. He was intense, I was intense, and we were both raised by single parents. Jim was like a mountain man who was also a brilliant scientist." She liked to call him Mr. Database. Every night after work, Gray would greet his wife by saying, "Hello, Donna Lee! I’m home, you lucky person!"

In 1995, Microsoft’s Rashid recruited Gray as part of a big-brain hiring spree. With fellow computing pioneer Gordon Bell down the hall, Gray tacked up a UNIX — LIVE FREE OR DIE or die license plate in his office and set about mentoring a new generation.

He turned a dorky Windows NT marketing concept ("Scalability Day") into an excuse to build TerraServer, which brought satellite imagery — previously the exclusive domain of intelligence agencies and weather forecasters — to the masses. Then Gray teamed up with astronomer Alex Szalay at Johns Hopkins University to port a massive star-mapping project — the Sloan Digital Sky Survey — to the Web, making the data accessible to professional astronomers, backyard stargazers, and students. Since its debut in 2001, SkyServer has become the most widely used astronomical resource in the world, sparking discoveries about dwarf galaxies, dark matter, and sonic waves triggered by the big bang.

To Gray, both sites were teasers for the coming era of data-centric science made possible by the proliferation of cheap sensing devices, very large data bases, and online interfaces. For life-science researchers, he was like an ambassador from the future who spoke their language. The morning he set sail for the Farallon Islands, he had collaborations under way with oceanographers, soil ecologists, and public health officials.

And he was at least as interested in the scientists themselves as in the petabytes of data they produced. "We connected so deeply," Szalay says. "Sometimes you make these kinds of connections very early in life or in graduate school. But by the time you get to 50, it’s rare to meet someone who is so much on the same wavelength. We talked this way, usually several times a day, for eight years."

Gray described his job at Microsoft as "making other people successful." When word went out that he was lost at sea, the scientists and engineers whose careers had flourished under his watchful eye marshaled their forces for their toughest test.

Three days after Gray set sail, on Wednesday, January 31, Swatland held a press conference on Yerba Buena Island. "We’ve searched 40,000 square miles of ocean," he said. "We cannot search indefinitely. It is always a hard decision when to break it off." Reports of sailboats disabled at Point Reyes and Stinson Beach just north of San Francisco had turned out to be blind alleys. Even a small boat typically casts a wide debris field as it sinks, with cushions, flashlights, trash, and gasoline bubbling up to the surface, but the Coast Guard had found nothing. Swatland announced that he would officially call off the search at 1 am Thursday.

The news did not sit well with the Friends of Jim at the press conference. When speculation among reporters turned to the notion that Gray might have evaded the searchers intentionally or committed suicide, Paula Hawthorn says, "I beamed right up to the front of the room and said, ’You don’t know this man. He would never have done such a thing.’ So they put me on TV. I said that Jim’s friends were not giving up."

The notion of searching for Gray with tools he helped invent struck a deep chord in the online world. When the hunt for James Kim intensified in December, some bloggers had suggested crowdsourcing a rescue effort by enlisting netsurfers to aid in the search online. Executives at CNET had also thought of trying to use remote sensing to find the Kim family, and a company called GeoEye announced that its Ikonos satellite would make a special pass over the Oregon mountains. But a pilot spotted Kim’s body the next day. Now the 21st-century paradigm for search and rescue would get a second chance.

The first step in any missing-person case is to make the subject of the search ubiquitous. As Gray’s serenely owlish visage propagated on YouTube, images of Tenacious were tacked up in marinas from Japan to Mexico. Slashdot readers furnished links to the programmer’s technical legacy while cracking grim jokes about the Blue Wave of Death.

Microsoft PR decided early on that it would keep the company’s efforts out of the news. But behind the scenes, Rashid let it be known that money would be no object in the search for Gray. If the Coast Guard was going to drop out, keeping search planes aloft required raising a private air force. Bill Gates personally offered Microsoft’s corporate account at a rental company called NetJets.

The lead developer on TerraServer, Microsoft’s Tom Barclay, took on the job of organizing the air search while coordinating efforts with Google to obtain satellite imagery. Of the archrival companies working together, he told a reporter, "We were competitors yesterday and we’ll be competitors tomorrow, but today we’re partners."

Then the Coast Guard did something unexpected — instead of calling off the search, Swatland redoubled the effort. He deployed two C-130 aircraft, three helicopters, three patrol boats, and four motor lifeboats to venture as far south as the Channel Islands off the coast of Santa Barbara, as far north as Oregon, and 300 miles offshore — an area the size of the Republic of the Congo. "I changed my mind because I didn’t have a warm fuzzy feeling we’d done everything we could," he says. "And I’d be a liar if I said all the publicity didn’t have something to do with it."

The only case Swatland could recall of a boat disappearing so completely was a fishing vessel called Relentless, which vanished in a busy shipping lane in 2004 while steaming toward San Francisco’s Fisherman’s Wharf with a catch of Dover sole. The captain’s family is convinced that the boat was rammed by one of the huge merchant ships churning in and out of the Golden Gate. The wreck of the Relentless has never been found. "You hit a steel fishing boat in a big ship like that, you probably feel it," Swatland says, "but a fiberglass sailboat like Tenacious? Maybe not."

After making a list of major vessels that could have posed a threat to Gray, the Coast Guard dispatched investigators to scrutinize ship’s logs and examine hulls for signs of a collision. Japanese ships already back in their home ports were inspected by local maritime authorities. But no telltale log entry or damage was discovered. Swatland admits, however, that a determined crew could scrub away the evidence: "Can I say with 100 percent certainty that none of the ships we checked did it? No."

Time was running out — if Gray was still alive, he had only a few days of food on the boat, and the weather along the coast was getting worse.

As the Coast Guard revived its search effort, the Friends of Jim finally got some hard data to work with. With the blessing of the Canadian Space Agency, a satellite called Radarsat-1 — equipped with cloud-piercing synthetic-aperture radar — flew over the search area with sensors blazing. Soon after, DigitalGlobe’s QuickBird made the first of three high-resolution passes, joined by GeoEye’s Ikonos.

In addition to the satellites, NASA volunteered a pilot scheduled for a training flight in an ER-2 — the civilian equivalent of a spy plane — to cover the coastline with a near-infrared camera. In the course of a few days, the strip of ocean outside the Golden Gate became one of the most thoroughly documented locations on the planet.

The incoming avalanche of data created a fresh set of challenges. Originally, Gray’s Microsoft colleagues and Vogels at Amazon were planning to use fancy data-crunching software to sift through millions of pixels for anything resembling a drifting boat. But these schemes were frustrated by the clouds moving in over the Pacific, which would have overwhelmed the algorithms.

Then Vogels remembered another resource that’s very adept at picking salient details out of blurry images: human eyes. Launched in 2005, Amazon’s Mechanical Turk is a service that enables employers to hire online workers for short-term tasks that computers don’t do well. If a city government wants to count its utility-pole inventory, for instance, it can pay netsurfers a pittance (in dollars or rupees) to click through thousands of street-level photographs, tagging the poles they see. Spotting Tenacious in a sea of gray seemed like the perfect test of MTurk’s "artificial artificial intelligence." On Friday, Vogels posted a request for volunteers on his blog with the headline "Help Find Jim Gray." The request raced through the online world, landing on the front page of Digg and getting a link in a New York Times story about the missing programmer. More than 12,000 volunteers signed up.

To increase the chances of finding the boat, Alex Szalay and his son Tamas — a student at Caltech — organized an alternate crew to analyze the same image data at Johns Hopkins, the University of Hawaii, and the Space Telescope Science Institute in Baltimore. The Szalays stayed up all night writing software to increase the clarity of the images. More seasoned analysts joined the effort from ESIP, the Federation of Earth Science Information Partners, a consortium of satellite vendors and federal agencies. "All these different communities working together, on a moment’s notice, with an incredible sense of urgency, to try to do the impossible," Szalay says. "That was very Jim."

Transferring hundreds of gigabytes of 8,192- by 8,192-pixel files into a standard format and tiling them into smaller pieces for distribution turned out to be tricky. When DigitalGlobe’s first batch arrived on Amazon’s servers, the files looked 100 percent black — a "heart-stopping moment," says Mechanical Turk director Peter Cohen. "That was our own ignorance," Vogels admits. "We went back to DigitalGlobe and said, ’There’s something wrong with these images.’ They told us, ’We’re looking at them now. They’re fine.’ It took us crucial hours to realize that there were bits we needed to strip out. Our team worked day and night to get those files up."

Thousands of online volunteers tore through the images over the weekend. The task was eye-numbing: Most of the tiles were a murky gray or bluish black, with occasional streaks and blotches that could be clouds, wakes, whitecaps — or Gray’s boat. One coder whipped up a Greasemonkey script to make scrolling through mass quantities of images easier. Meanwhile, Szalay’s astronomers and the ESIP volunteers were hard at work. A particle physicist named Julian Bunn spotted a Tenacious-like blip lurking under a cloud. Swatland pledged that if anything turned up, the Coast Guard would lead the rescue effort.

By Monday afternoon, eight days after Gray went missing, the Amazon volunteers had scrutinized roughly 30,000 square miles of water. About 20 images were tagged as "likely," and one was tagged "highly likely," Vogels says. Promising images were flagged with comments and forwarded to a panel of expert satellite analysts convened by Szalay and led by venture capitalist David Tennenhouse, former director of Darpa’s Information Technology Office.

But even with a handful of likely targets, there was another hurdle before Microsoft’s Tom Barclay could dispatch search planes: Because days had passed since the objects in the images were caught by the satellites’ sensors, they could have floated miles from their original locations. The Friends of Jim needed a way to forecast where a 40-foot sailboat would drift, given the state of the weather and surface currents.

Oceanographer Jim Bellingham was already on the case. Chief technologist at the Monterey Bay Aquarium Research Institute, Bellingham was another young scientist who had benefited from Gray’s patient mentoring. A typical field program at MBARI consists of putting dozens of robot gliders and other sensing devices into the sea to measure such variables as temperature, nitrate content, and the presence of bioluminescent organisms. Last year, Gray helped Bellingham design a set of "digital workbenches" to help the institute better analyze rapid influxes of real-time data.

Now similar tools were needed to build simulations and to plot drift trajectories. Bellingham assembled a team of ocean modelers from the US Navy, NASA’s Jet Propulsion Lab, and Oregon Health & Science University. For up-to-the-minute data about currents, they tracked Coast Guard radio buoys and dialed into a high-frequency radar network recently installed by the state of California to monitor coastal conditions. Then they posted GIF animations to the Web showing where an object seen by a satellite two days before would likely be located. "We pulled out all the stops," Bellingham says. "If this had been a real field program, it would have taken months to spin all this up."

In some cases, the drift team relied on ocean data from the same types of buoys that Gray himself had used for a climate-change study in 1994. "Now we were using them to find Jim. That was bittersweet," says Oracle’s VP of embedded technologies, Mike Olson, who had also worked on the climate study.

But just as Szalay’s image experts were identifying the most promising targets, the weather intervened. Rain and high winds swept down the coast, delaying some flights. When the sky finally cleared, all the leads were hunted down, but the searchers came back empty-handed.

Vogels is still haunted by the notion that the "highly likely" target may in fact have been Gray’s boat. "It’s not that we didn’t find anything," he says. "That image might very well have been Jim. The drift analysis was right. But we had to wait two or three days before sending out a plane because of the weather. By then, nothing was there."

As the satellite drama unfolded, the Friends of Jim were also working other angles. In the aftermath of Hurricane Katrina, an organization called the Wireless Emergency Response Team had located survivors in New Orleans by flying a portable wireless tower over the flooded city. Barclay proposed that WERT do the same thing over the ocean to ping Gray’s smartphone. To pull it off, he needed a twin-engine plane and a pilot capable of ferrying the device on a risky long-range flight from Mexico to the Canadian border — the entire length of the search area by that point. Late one night, Barclay got a call from Oracle’s head of server technologies, Chuck Rozwat, who said that Larry Ellison was volunteering to do the job himself in his own private jet. But WERT backed out of the plan, claiming its crew was unavailable.

For all their technical and financial might, the Friends of Jim were out of options. The massive push to create new tools for search and rescue had been a success — but the man who inspired the effort was still nowhere to be found.

As Gray’s friends lost hope that he was alive, Carnes gazed out at the water from her deck on Telegraph Hill. "I would go out there and have these ridiculous conversations: ’Come home, wherever you are, just come home, in whatever form, I’ll give up an arm or a leg, just let me find you,’" she says. Finally she decided it was time to go to sea herself.

On February 11, she chartered a fishing boat to take her and a marine search expert named Bob Bilger to the Farallones. An avuncular, walrus-mustached Minnesotan whose day job is delivering boats to their owners, Bilger organized a team that was able to predict the location of the Coyote — a boat wrecked en route to an around-the-world race in 1992 — within 15 nautical miles. His goal when embarking on a search is to "get inside the mind of the skipper," he says, while gathering every scrap of data he can about the boat and ocean conditions on the day the vessel went astray. Bilger takes no fee for his searches, saying that it’s his way of showing gratitude to the boating community for being generous with him when he was younger.

Onshore access to Southeast Farallon Island is restricted to scientists, but House Speaker Nancy Pelosi’s office arranged clearance so Carnes and Bilger could talk to Brett Hartl, the young naturalist who may have seen Tenacious just before it fell off the map. Looming out of the mist, reeking of guano, and devoid of all but scrub and government-issue architecture, the island is hospitable only to the dozens of species of seabirds and pinnipeds that breed there. So many great white sharks slither through the water nearby that naturalists toss in old surfboards just to video the attacks. Scores of ships have met their doom on the jagged outcroppings that 19th-century sailors called the devil’s teeth.

It seems like an inauspicious place to deposit your mother’s ashes, but Ann Gray made that specific request in her will. Carnes’ father, Don, also wanted to be scattered at sea, and the two urns sat side by side in Jim and Donna’s kitchen for months. Last Christmas, Jim invited his daughter along for the trip, but Heather thought baby Sam was too young for sailing.

Both wind and water were relatively calm as Carnes passed the Point Bonita lighthouse, as they had been for her husband two weeks earlier. But as she got close to the 15-mile marker that Gray mentioned in his last conversation, the boat entered a maze of floating debris. Winter storms in Oregon and Washington had launched a ragged archipelago of logs, nets, and other flotsam into the Pacific, which had been making their way down to the Bay Area for weeks. "There were so many logs, hundreds of logs, so much lumber in the water," Carnes says bitterly.

Though Gray was never interested in racing, his boat — a C&C 40 — was built for speed, with a lightweight hull, an unshielded propeller, and an 8,000-pound lead keel for stability. These features make boats like Tenacious graceful and maneuverable in the hands of a skilled sailor like Gray. But they leave the boat vulnerable to damage from heavy objects in the water. Bilger estimates that if a log had opened a hole in the hull that was 6 inches or more in diameter, Tenacious would have taken on a thousand gallons of water a minute. "I can picture a million scenarios that would have put a hole in the bottom," he says, "with enough water coming in that Jim had no way of shutting it down, slowing it up, or fixing it."

In fact, Tenacious might have been even more vulnerable to hull damage than the average C&C 40. Ten years ago, a saltwater intake hose on the boat frayed against the engine. By the time Gray discovered the leak, the water was waist-high in the cabin. If the boat had never completely dried out, the balsa-wood core of its fiberglass hull could have slowly rotted from within.

Plus, even on a clear day, the water between San Francisco and the Farallones is a washing machine. Entering or leaving the Golden Gate, sailors have to skirt two shipping lanes that straddle a treacherous area of turbulence known as the Potato Patch. A Microsoft engineer named Phil Garrett determined that on the day Gray set sail, the favorable morning winds turned against him in the afternoon, gusting from the east at more than 8 knots, something even a seasoned Bay Area sailor would not have expected. Those stiff winds and an outgoing tide would have made it nearly impossible for Gray to make it back to Gashouse Cove by sunset, even running his motor. And in the dark, it would have been tougher for him to avoid hitting heavy objects in the water — and harder for the crew of a merchant ship, trying to stay on schedule, to notice a small fiberglass boat gliding in front of them.

Like many sailors, Gray could also be slightly careless about safety equipment. He stashed his emergency radio beacon — designed to deploy automatically underwater—on a shelf in the companionway, below deck, and didn’t always remember to bring it up before leaving the dock, according to Carnes.1 If a log had opened a big enough hole in the hull, Bilger estimates, Tenacious could have sunk in as little as 30 seconds; hardly enough time to fetch the EPIRB or start inflating a dinghy with the foot pump stored under the cockpit seat. If something bad did happen out there, Jim Bellingham says, Gray’s unflappable attitude may not have served him well. "With Jim being an engineer, you can imagine him thinking, ’I can fix this’ — and then the whole thing snowballs. He was a level-headed, steady guy who wasn’t likely to panic. Which is maybe too bad, because a less-competent person might have grabbed the radio and shouted for help."

The mystery of the missing debris might not be a mystery, Bilger says. If Tenacious took on water, its engine and gas tanks would have sunk the boat stern first; any loose life rings or ropes might have been scooped up in the bow and sucked under the waves. But until the boat is found, the search expert is not ready to say definitively what happened to Gray. "I deal in facts, not hearsay or speculation," he says.

There is one more scenario that Bilger refuses to absolutely rule out — that Gray did something completely unexpected and sailed away. He’s the kind of guy who does exactly what he wants, when he wants, doesn’t ask anybody’s permission, and may or may not explain himself later. The problem is, I can take the same set of facts, run Jim south, and have him leaving. Everybody who knew him thinks that’s extremely far-fetched. But strictly speaking, the facts could go either way."

Gray’s friends and family firmly reject this scenario, which has become a popular explanation for his disappearance among Bay Area day-sailors with Jimmy Buffett tendencies. While cynicism and irreverence are not hard to come by among old coders, even Gray’s most hard-boiled cronies dismiss the notion that he vanished on purpose, for reasons ranging from love and lust ("He said his sex life with Donna was still great") to cash ("He would never have walked away from all that Microsoft money").

As winter turned into spring, Carnes employed a private company to comb the ocean floor north of the Golden Gate with side-scan sonar and remote-operated underwater vehicles. But like the search, this three-and-a-half-month salvage operation, too, turned up nothing.

On May 8, a Wikipedia user appended a phrase to Gray’s entry: "presumed dead." Gray’s daughter finds this hard to accept. "I don’t believe that my dad is dead. I don’t think they’re going to find anything," Heather Gray told me. "I think he could be adrift."

When a death requires a presumption, it’s loved ones who can become adrift, says therapist Pauline Boss, author of two books on what she calls ambiguous loss. "The only way you can live is to keep two opposing ideas in your mind at the same time: ’He’s dead’ and ’maybe not.’ The bad side of living that way is that the stress is unbelievable. We’re used to being able to solve problems."

Gray was one of the best and brightest in a generation of problem-solvers, and also one of the most humble. When conference hosts tried to introduce him as a database guru or god, he would say gently, "I’m just a programmer." Even his disappearance proved to be an act of mentoring, providing a template for networked search-and-rescue methods that may save countless lives in the future. But for now, his family, friends, and colleagues at Microsoft, Amazon, Google, NASA, and laboratories all over the world are left unmoored.

"Despite our knowledge and technology and the applied brilliance of scientists like Jim, we all ended up feeling helpless, " Carnes wrote in an email. "Of course, Jim would read what I’ve just written and say: Oh, Donna Lee, first you live and then you die. Then he’d crush me in a bear hug and we’d watch some boy action flick. But he is not the one left searching."


Jim Gray and grandson Sam build a sand castle at Ocean Beach, San Francisco, on Christmas Day 2006.

Jim Gray on Aloha Lake near Lake Tahoe during a backpacking trip in 2005.

At home on Telegraph Hill in San Francisco (from left to right): Donna Carnes and Jim Gray, with grandson Sam, daughter Heather Gray, and son-in-law Sam Long.

At his mom’s home in Millbrae, California, Jim Gray celebrates grandson Sam’s first Christmas in 2005.

Contributing editor Steve Silberman (digaman@sonic.net) wrote about drug-resistant bacteria in Iraq in issue 15.02.

Feature Anatomy of an Accident Lost at Sea