by Brandon Webb
John and I were both southern California surfers, and we hit it off right away. If your picture of a Navy SEAL is a big, chiseled, pro-football type with rippling muscles and a fuck-you glare, then you never would have pegged John for a SEAL. A slender five-eleven, with sandy blond hair, an oval face, an affable smile, and quiet confidence, he looked like your average skinny surf bum.
John was a competitive swimmer almost before he could walk. His first swim meet, at age five, was abysmal. The other kids dived into the water and swam to the end of the pool and back before John had even touched the other side. That was it for John: He never lost a meet again, and that capacity to take fuel from failure would become his signature gift.
The water was John’s passion and driving force. An excellent athlete, he played competitive water polo throughout his school years. During his senior year of high school his dad took him to become scuba-certified, and John was so far ahead of everyone else in the tests that the instructors started calling him Neptune. He could have gone on to university on a water polo scholarship. But he wanted more than anything to join the Navy and become a SEAL. Four days after his high school graduation, he was on his way to Great Lakes, Illinois, to attend Navy boot camp. He was barely seventeen. A year and a half later he was starting BUD/S.
John had no illusions about how tough the selection process would be, but he was determined to make it through no matter how hard it got. Of course, nobody goes into BUD/S planning to fail. Your first day on that asphalt grinder at Coronado you hear everyone around you saying, “Hey, man, no way I’m quitting!” And a few days later, as you drag yourself out of your bunk in the frigid predawn darkness, bruised and battered and beaten, and you hear the morning silence split by the bone-jarring clanggg, clanggg of that damn brass bell, you know another sorry-ass motherfucker has thrown in the towel. My class started with 220 candidates; by graduation seven months later there were twenty-three of us left. It’s easy to talk a big game, but when the reality of BUD/S starts to sink in, people crumble. Not John. He was so focused, so intent on plowing through and going straight into the SEALs, that it was impossible to imagine him not doing it.
And yet, just as with that first swim meet at age five, his first time out he did fail.
BUD/S Class 205 began in December 1995. It was near the tail end of a record-length El Niño surge, and major storms were pummeling California. By the time they reached Hell Week, it was one of the coldest on record. John ended up with pneumonia and was forced to call a halt.
Getting rolled from BUD/S just about killed him. Not the pneumonia—the blow to his ego. He wasted no time on self-recrimination, though. That fuel-from-failure thing again. It wasn’t the first time he’d suffered a bitter defeat on the way to triumph, and it sure as hell wouldn’t be the last.
There’s a common idea in the SEALs that says, if you don’t make it through BUD/S on your first try, you need to go out and get some experience before you come back for a second shot at it. John decided to take a turn as a naval police officer. He wangled an assignment to Lackland Air Force Base in San Antonio to go through a six-week training course, and upon graduating was assigned to police duty at the naval station in Guantánamo Bay, Cuba. After eighteen months of breaking up bar fights and keeping the peace, he showed up back in Coronado, ready to do BUD/S again. This time he went the distance, and graduated Class 217 in mid-’98, just a few months after I finished Class 215.
• • •
As new guys at SEAL Team Three, John and I went surfing together as often as we could. We also shared an aspiration to become successful in business, and during our time together at Team Three we talked a lot about being entrepreneurs and all that we wanted to accomplish in our lives.
At the time I had begun investing in real estate and having some modest success, to the extent that I owned my own home and rented out a guesthouse on the property. I’d studied Robert (Rich Dad, Poor Dad) Kiyosaki’s approach to building a portfolio of income-generating assets, and I was convinced real estate was the way to go.
John wasn’t especially interested in real estate. He wanted to build something. He wanted to create and run his own business. Actually, that’s not saying it right: He didn’t just want to run his own business—it was more like a burning, all-consuming drive. He had to.
Right away I noticed that John had a distinctive quality of absolute confidence. When he talked about something happening in the future, it was so vivid, so real, you knew it would happen. A common experience for SEALs is that, once having been part of this incredibly elite team, it can seem impossible to imagine that any other experience could come close, as if the path of achievement were by definition downhill from there on. That wasn’t John’s view at all. “I have bigger fish to fry,” was how he saw it. And he was 100 percent positive that he would build something that would become hugely successful.
Figuring out exactly what that would be . . . that was another story.
In the spring of 2000 he asked his lawyer father, Michael, to help him form his own corporation as part of a plan for a restaurant that incorporated a gigantic man-made wave, so that people could come to the restaurant and surf while they were there. He became interested in buying the rights to a British-made amphibious vehicle and distributing it here in the States. He tried his hand at stockbroking. It became a running joke at Michael’s office: John calling and yet again changing his articles of incorporation to fit his latest new idea. Over the next few years that corporation’s name would change six times—and there were dozens of other business ideas that never even made it to the corporate-naming stage. Nothing quite came together. To a casual observer, John’s serial-entrepreneur efforts might have seemed no more than a string of harebrained ideas that would never amount to anything. It would be a few years before the evidence proved it, but that casual observer would have been dead wrong.
Meanwhile John and I had continued in our SEAL careers on parallel tracks. When I went to Golf Platoon he joined Bravo, our sister platoon, and deployed to the Middle East at the same time we did. While we were part of the amphibious readiness group (the one that ended up rushing to the aid of the stricken USS Cole), Bravo was stationed in Bahrain, where they engaged in noncompliant ship boardings, enforcing UN sanctions against Iraq. On that deployment John proved himself one of their team’s most outstanding performers.
A hostile ship boarding, called a VBSS (visit, board, search, and seizure), is a high-speed, precision operation. After sneaking up alongside the hostile ship with your fast boats, you have to get your guys up and over the ship’s railings before the onboard crew of smugglers and pirates even realizes you’re there, because the moment they know they’re being boarded they’ll take aggressive countermeasures. In the case of a smuggling ship on the Gulf, they’ll haul ass for nearby Iranian waters, where you’re legally powerless to do anything.
During the critical split-second board phase of one of Bravo Platoon’s VBSS operations, one of the guys fired a grappling hook that failed to catch on the pirate ship’s railing.
“I was still processing the fact that the thing hadn’t taken,” John’s OIC explained afterward, “and in a fraction of a second John threw another hook up there by hand.” John’s hook caught, and within the next few seconds he had scuttled up the line and was up there on the railing laying down suppressing fire with a squad automatic weapon (SAW) while the rest of the boarding team crawled up the line after him. “I’d never seen a reaction time like that before,” his OIC added. “And I’ve never seen one since.”
When our deployments ended, John and I were both coming up for reenlistment, which would mean a decent cash bonus if we opted to stay in. I was married by this time, John was engaged to his girlfriend, Jackie, and we were both thinking about the financial demands of starting a family. I took the bonus and stayed in, moving from Golf to Echo Platoon, which was scheduled to go overseas later that year (though we could hardly have guess
ed we would end up in the mountains of Afghanistan hunting for terrorist training camps). John took a different path. When Bravo Platoon got back from their deployment at the end of 2000, John surprised Jackie by saying he wasn’t going to reenlist. He loved being part of the teams—but he wanted out.
John was a valuable asset (he was hell on the M60 machine gun), and our command didn’t want to lose him. The commander of SEAL Team Three offered to raise his bonus, but John turned him down. The offer went up; he turned it down again. They finally got up to sixty thousand dollars (an unheard-of amount), but he turned that down, too.
As he said, he had bigger fish to fry.
John left the service in early March 2001, and he and Jackie were married a few weeks later. By this time Jackie had her master’s degree in food science and had gotten a good job offer from National Food Laboratories, up in the San Francisco Bay Area. Since John had enlisted right out of high school, Jackie suggested he take this opportunity to go back to school and get a degree. “I grew up on the East Coast,” she says, “in a family where it was ingrained into us that the way to success was to go to college and get a good job. I really couldn’t picture any other path.” John didn’t see it that way, and he didn’t give much of a damn about school, but he agreed to give it a shot. They moved to the Oakland area and he enrolled in a community college there while he looked for a job.
John found college life frustrating and at times infuriating. The other students were only a few years younger than he was, but to John they seemed like kids who had seen nothing of real life. It was hard to sit there listening to those professors spouting their academic worldviews, armchair-quarterbacking events halfway around the world—events John had seen up close in all their gritty reality. While I was tracking down Taliban and al Qaeda forces in the mountains of Afghanistan, John was sitting in a classroom being bored out of his mind.
Meanwhile, he continued coming up with idea after idea for new businesses. Every time he hatched a new concept he’d pitch it to Jackie, who listened and did her best to temper her own natural skepticism. Earlier that year, just before they were married, John had presented Jackie with the idea of putting ex–military personnel on domestic passenger flights. “Our biggest national threat is in the air,” he told her. He changed his corporation’s name to SkyGuard and worked with a martial arts master to develop a simplified version of Okinawan karate that flight attendants could employ in the narrow confines of a passenger airplane aisle, with a curriculum they could cover in about two hours.
Jackie had thought the idea was a bit far-fetched. Then 9/11 happened. “Oh, my God,” she told him. “You were right!”
Still, the SkyGuard idea did not come together. Jackie adored John and believed in him. But so far none of his brilliant ideas had panned out—and they had to eat. John needed to get a job.
Toward the end of 2001 John got a job offer with the sheriff’s department in Half Moon Bay, a sleepy San Francisco suburb. With eighteen months as a naval police officer in Guantánamo Bay, plus four years in the SEALs, he was the very definition of “overqualified.” Be that as it may, the job required that he enroll in a five-month program at the police academy there. He started in January 2002.
John was the best student his instructors had ever seen at the academy, both physically and academically. Which was interesting, considering that John had never before been more than a mediocre student (unless the subject involved athletics). But over his years in the service he had learned how to focus his energies on whatever task he saw as important, and he was killing their standards. The jock who didn’t care about school had become the ultimate student.
One week before graduation, the cadets were practicing one-on-one takedowns. John was disgusted at how laid-back his classmates were as they went through the motions. When his turn came and a classmate faux-attacked him, John took the guy down for real, and hard. He didn’t injure the man, but that dude was down before he had a clue what had hit him.
The instructor suspended John on the spot. After a hasty conference, the administration judged him “too aggressive” for the academy. With a week to go till graduation, he was booted out of the program.
John was devastated. He could joke about it to Jackie (“I would’ve been better off over in Oakland, where there’s a murder every day!”), but it was no joke. Being kicked out of the academy also meant the police job was gone. The young couple had just bought a home and were now carrying a substantial mortgage. Jackie’s job notwithstanding, they really needed John to generate an income.
This was the spring of 2002, and the so-called War on Terror was just hitting its stride. My platoon was on its way home from Afghanistan, to be replaced by others. Things were already heating up in Iraq, and those on the inside could sense the drumbeat to war. The government was stepping up its use of contract security agents overseas. As part of Team Three, John’s AO (area of operations) in the SEALs had been the Middle East, so he was highly qualified. If the Half Moon Bay police department couldn’t see a way to use him, private security companies like DynCorp and Blackwater sure could. And the money was good.
So John signed up, and for the next few years he was in and out of the Middle East, working as a private contractor.
In the summer of 2002, when Hamid Karzai became president of Afghanistan’s interim government, John was there as part of his security detail. A year later, as the dust settled in Iraq from the U.S.-led Shock and Awe campaign, John was there sweeping the country for WMDs. When L. Paul Bremer became in effect the interim chief executive of Iraq, John was on hand, guarding him as well.
Those years were a terrifying time for Jackie. It seemed to her that every night there was news about yet another roadside bomb in the Middle East—and all she could do was hope John was nowhere near it. She was right to be terrified, because there were in fact times when he was quite near the action indeed.
Especially one pivotal day in late January 2004.
• • •
By 2004 the situation in Iraq had seriously deteriorated and was getting more dangerous by the day. John and an ex–Green Beret buddy, Ron Griffin, would spend each day hazarding the streets of Iraq, then get together in the evenings to talk over what they’d seen during the day and discuss the tactical failures they’d witnessed.
One major source of problems lay in the vehicles they were driving, which were typically some sort of high-end SUV, retrofitted with armor plating. The problem was that everyone on the street knew who was in these vehicles, because nobody over there but Americans was driving those models. Our guys might as well have had neon signs saying, “We’re Americans! Shoot at us!” The bad guys would stand up on overpasses with binoculars, scope out one of these cars, and suddenly you’re getting an RPG up the tailpipe. (Ron called them “to whom it may concern shots.”)
And it wasn’t only a matter of how recognizable the cars were. These vehicles just weren’t designed for the punishment they were taking. John and Ron were constantly wrestling with fuel-incompatibility issues, suspension system failures, problems with doors, windows, and other secondary electromechanical systems, and all sorts of mechanical fuckups. Under normal circumstances failures like these would be minor annoyances. In conditions of urban combat they could be catastrophic.
“If someone doesn’t do something about these vehicles,” John said to Ron, “we’re going to lose a lot of our guys.”
On January 27, 2004, John was part of a convoy on a mission through the mean streets of the city where he and Ron were working. No matter how skillful the driving or how well the three drivers kept their distance, there was no way their vehicles could not stand out like three-piece suits in an inner-city street fight. Sure enough, the convoy was ambushed. The vehicles in front managed to escape the kill zone and get away, leaving John and his companions in the hot seat. A slew of hostiles came up from behind, and John and his buddies’ car started taking heavy fire. Accord
ing to the after-action report, armor-piercing rounds were fired into the vehicle through their windows. Manning the machine gun in back, John returned fire out the shattered back windshield while the driver practiced every evasive tactic he knew.
Which was when one of the vehicle’s “safety” features nearly got them killed.
A grenade blew up under the chassis, severing one of the car’s brake cables and causing the vehicle to lock up and come to an instant and complete stop.
“Motherfucker!” the driver said. John’s only comment was another volley from the big gun.
Back at base, Ron was having lunch when he and a few other guys heard the calls coming over: “Contact! Contact! Contact! . . .” Ron and the others jumped into two cars to form an immediate reaction force, get out there as quickly as possible, and pull out any survivors.
Meanwhile, their vehicle immobilized, John and his two teammates had no choice but to hoof it. John continued shooting out the back of the car, laying down enough cover fire so the other two guys could start moving out before he quit and joined them. When you’re shooting an automatic weapon in an enclosed space, it isn’t kind to your hearing. And John did not go light on bullets. From that day on he was deaf as a post in his right ear.
The three went on foot now, winding their way through some back streets until they found a friendly cabbie who stopped and turned over his car keys to them. They thanked the man, hopped in, and quickly realized the cabbie hadn’t done them much of a favor: The damn thing was on its last legs. They made it another quarter of a mile before the cab quit on them.
Back on foot again. Eventually they found a junkyard area they could slip into and get some concealment. They holed up there until one of the two reaction vehicles caught up to them and got them out.