The Hustle

by Doug Merlino

  …

  “It was like I was in a play,” Chris Dickinson says. “It was almost a role. I just lived it for all it was worth.”

  We are sitting in the basement office in his spacious house in South Seattle, a few miles north of Eric’s place. Chris, who has just gotten home from work, has thrown his suit jacket and tie over a sit-up machine in front of his desk. He sits on the other side, his feet up. Behind him, a seven-by-four-foot banner with PRINCETON written in orange on a black background hangs on the wall. Framed pictures of his wife, Ashleigh, and kids—four-year-old son Jack and two-year-old daughter Hannah—stand on the desk and on the shelf behind the couch where I sit.

  On the far wall hang two framed commendations from the Lakeside School for “Distinguished Service”—one given to Chris’s maternal uncle, a founding partner in one of Seattle’s prominent law firms, and one awarded to Chris’s father, Cal, who made partner at another of Seattle’s principal law firms and served on both Lakeside’s alumni board and board of trustees for many years (“Widely read and rational … a calm, reasoned statesman in a time of turmoil,” Cal’s reads).

  Chris and I are speaking about his emergence as a star athlete, with frequent visits from Jack and Hannah, who poke their heads in the door, dart in to grab a corn chip from the bag Chris holds in his hands, and then, giggling, scurry out. Chris tells me that he still wonders about the change that overcame him in middle school as a rapid growth spurt transformed his body and social standing.

  “All of a sudden I was perceived as being good-looking and this athlete,” he says. “My dad used to talk about Rudolf the Red-Nosed Reindeer and say that it was a terrible message, because nobody liked Rudolf, nobody wanted to play with him, and all of a sudden when Santa liked Rudolf, he was the most popular guy. It was like that. Physically I changed and all of a sudden my entire life changed. But I probably carry some of the insecurities I had still today because there was such a massive perception change associated with my physical appearance.”

  Chris, who still looks like a movie version of a high school sports star—tall, with short brown hair, blue eyes, and a strong jaw—speaks in a deliberate, sometimes almost tortured pace. Sports and what they mean to him is a subject he has spent a lot of time mulling over. “It’s like larger than life,” he says. “You’re a big fish in a small pond. Seattle’s a small city; it was easy to take it a little too far. But literally, it was like a drug.”

  In the old photo taken right after we won the Western Washington AAU championship, Eric and Chris both smile and hoist the trophy and appear completely content. Looking at it now, it strikes me how rare it was to see either of them so relaxed and comfortable.

  “At that age and time, my energy and thoughts were not competing,” Chris says of our team. “There was joy in playing, just a visceral connection to the game. It was very pure. It just flowed. I loved those guys. If I could see them now, I’d just give each of them a big hug.”

  Chris and Eric both found escape and freedom on the court. Though they came to Lakeside from nearly opposite backgrounds, each struggled to fit his personality with the institution. Both of them now often refer to the “roles” people are expected to play—Eric as a black man, Chris as the son of a prominent family.

  Eric is especially conscious of this process. He remembers that in ninth grade, Chris adopted a little bit of “black” style—he hung out with Eric, got into rap, and learned to break-dance. Eric noticed that some other white guys in Chris’s clique gave him a hard time. Eric thought Chris’s friends felt uncomfortable with someone trying to act differently—they wanted to reel Chris back in so they wouldn’t feel threatened.

  I also had my own memories of Chris, primarily of our first meeting, when we were supposed to fight at the eighth-grade dance. At the time, I saw Chris as my opposite, a “natural aristocrat” from the wealthy Madison Park neighborhood who was an easy fit at Lakeside. We were in reality more like mirror images of each other, two kids hiding their insecurities with macho posturing. In my case, I was trying to blot out the thought that I was a dorky loser. Sports stardom seemed like a way to cover all of that up. But by the time I met Chris at age fourteen, I was starting to realize that I wasn’t big enough, strong enough, or fast enough to go very far in athletics. My face-off with Chris brought this home—despite my bluster, I knew that there was no way I would beat him in basketball or a fistfight. It was hard for me to accept, and the reason our initial confrontation stayed with me all these years.

  When I mention my memory of our first meeting to Chris, I have to laugh when Chris tells me he has only a “faint recollection.” It’s the first time either of us has brought it up since the incident happened. “I do remember how visceral the whole thing was, the whole Bush-Lakeside thing, and how big a thing basketball was, you know? And girls and all that,” Chris says. “I bet you the exact same stuff was playing with both of us.”

  As Chris and I talked as adults, I realized that he, Eric, and I were all working through a lot of the same things, just from different angles. In the end, Eric and I got by for several years, but we both finally had to leave Lakeside to feel comfortable in our own skins. That wasn’t an option for Chris.

  Chris’s family was well established at Lakeside by the time he enrolled. His older brother and sister were athletes and popular students at the school. Chris’s dad, Cal Dickinson, graduated from Lakeside in 1949, went on to Harvard, a stint in the navy, and then back to Harvard Law School, where he roomed in the same boardinghouse as future Supreme Court justice Antonin Scalia. When Cal returned to the Northwest, he took a job with Perkins Coie, a white-shoe law firm.

  At work, Cal specialized in industrial-labor law, handling cases for Boeing. He became known outside legal circles for his involvement in civic causes. His name appeared on committees to clean up the waterfront, develop the downtown shopping district, and build roads and parks. There were also his years of involvement with Lakeside.

  Chris brings up his dad frequently in conversation—Cal’s success seems to present both a model to follow and a challenge to meet. “My dad walked the walk, man,” he says. “I mean, he grew up in an environment where you achieved, then you provided. Back then, that was your frickin’ role. You weren’t supposed to be emotional and take care of yourself and love yourself, you’re supposed to go to work and be a man.

  “Even if he was that guy that grew up in that culture, he always wanted to love us and take care of us and grow up to be a good husband. It’s not like you’re always successful, sometimes you suck, but I always perceived that he had a very loving and pure intent.”

  By the time I meet Cal, I expect a stern, analytical lawyer. I’m surprised to find a soft-spoken, reflective man. “I think Chris has felt a lot of pressure to live up to what he sees as my accomplishments,” he tells me.

  Instead of shrinking before his dad’s achievements, Chris steered into them. Most notably, he was president of the Lakeside alumni board, a job his dad had held decades earlier. He laughs when he talks about it. “I just realized that I couldn’t be my dad,” he says. “It was funny being in that same position, thinking, ‘That’s what my dad did.’ You find yourself just walking in your parents’ footsteps. Like the first time I dropped Jack off at school it happened to be right behind my parents’ house. And I remember driving up the street, turning the corner, and then being in front of my parents’ house. It blew me away. It was like coming full circle. Like, I’m right back, my kids are right where I was, in the shadow of my parents’ house.”

  That night, as we speak in his basement office, Chris buzzes with energy. He’s just home from his job, where he brokers employee health insurance plans between businesses and insurance companies. At the beginning of our conversation, he takes out a yellow pad of paper and writes “Doug” on the top, but ends up doodling geometrical shapes on it. As we speak, Chris begins to stretch on the floor. I find it disconcerting at first, but then realize that this kind of multitasking must be a habi
t of someone driven, short of free time, and very athletic.

  Several months earlier, we had met at six on a Tuesday morning at his gym in the Belltown neighborhood north of downtown Seattle, only a few blocks from where Damian and I had seen Myran. The place was one large room with a hip, industrial feel—brick walls, a high ceiling crisscrossed by exposed wooden beams and silver venting ducts. Half of the space was filled with workout machines, the other covered with mats. In one corner, a small class mimicked an instructor’s yoga poses.

  Chris was in the middle of training for an Ironman triathlon, which he was due to run in a few months. To complete the race, he would have to swim two and a half miles, bike 112 miles, and run a full marathon. His training regimen was intense. Before starting to warm up on the treadmill, he warned me: “Last time, I had to vomit.”

  It was easy to see why. After a short jog, the routine was nonstop and grueling. The exercises included jumping back and forth over a foot-high orange cone while twisting around in the air; shuffling sideways while tossing an eight-pound ball to one of the gym’s trainers; and standing on one leg on an eighteen-inch-high box and then lowering himself to the mat before pushing back up. Within minutes, his face was dripping sweat. When I asked what was motivating him, he told me, “I want to see if I can make it. You’re out there all by yourself. You either do it or you don’t.”

  By the time we speak in his house, Chris has run the race. He says it’s still hard to describe the experience. “There’s nothing like feeling—it makes me almost emotional—like I did at different times on that race. Before it started, when I was facing all the preparation I’d done and there were fifteen seconds before the gun went off, I had tears rolling down my cheeks, and everybody else on the beach did, too. It’s palpable. You don’t even know what to do with it. And to be running on mile twenty of the marathon and I’d never even run a marathon before? And I’m all by myself in the dark? Man, you can’t have that unless you do it.”

  He continues, “It wasn’t like I was trying to smoke somebody. I had a little bit of competitive juice, but some guys get so attached to beating the guy in front of them. I sort of released myself a little bit, like I wanted to win but I could also see life from just, ‘Screw it, why do I need to be like that?’

  “And then the family was with me, they surprised me, and I ran with Jack holding hands for a while and we ran across the finish line together. I’ll never experience that in my life, even if I do it again, I’ll never have that first time again. It was like having a child. Nothing will be like having our first kid, but it was akin to that. It was special. Those things just define you because they are who you are and working through that adversity.”

  The experience stood out in part because it was something with a clear goal and a defined set of steps necessary to achieve it. In real life, Chris says, things get compartmentalized. You are a husband, a father, a worker who brings home money to support the family. In each role you try your hardest, but how do you know you’re doing it right? You get in a chute and start running. Your old identity slips away. In some ways, Chris says, the Ironman was an attempt to access the old athletic drive that had been buried, but to do it for the sake of personal challenge, not to make himself feel good by beating other people.

  At the race, all the merchandise on sale—Ironman biking shorts, hats, T-shirts—made Chris feel a little sick. He saw it all as another way to establish an identity and build the ego, to go around saying “I’m an Ironman.” Chris tells me, “I’d see people wearing that stuff head to toe and I didn’t associate with that at all. It wasn’t about that. I wouldn’t put a bumper sticker on my car.”

  The discipline it takes to complete an Ironman triathlon, as well as Chris’s continuing interest in Native American spirituality and meditation, seem a way to get a handle on a life that—along with the culture around it—is constantly accelerating, or at least an attempt to slow things down just a little bit.

  We take a break from speaking in Chris’s office to go upstairs and have dinner with Ashleigh, Jack, and Hannah. Over steak and asparagus, Ashleigh—who has taken off from nursing until the kids are in school full time—describes visiting an open house at a private school earlier in the day. She and Chris are trying to decide where to send Jack to kindergarten. They’ve ruled out the local public school, but are pondering options for private schools—should they send him to one with grades, or one without? How much pressure is too much for a kid?

  “It’s weird having a massive waiting list to a school,” Chris tells me after dinner. “When a preschool has a waiting list and then you feel like you’re into the club when you get in, it’s weird. The politics of Madison Park are totally in play, too, so not only are you competing but you’re in this weird social environment and it’s just very peculiar. You have to play the game and you feel like you do, you have relationships with people”—Chris takes a deep breath—“it’s all new, but it’s very weird and it starts very early.”

  Unlike twenty years ago, when it was normal for kids like us to play several sports and have other hobbies as well, Chris says it’s now common for children to begin focusing on a single sport as early as first grade. The idea is to get good enough to eventually draw the attention of high school admissions officers and college recruiters. “You get a sense nowadays of that, that it’s like, Jesus, you know, the envelope’s been pushed in some inappropriate ways,” he says.

  Still, you have to do what’s necessary to prepare your kids. The reality, Chris says, is that the world has become more competitive, and the Internet is only fueling the speed of that change. “Your ability to comprehend, process, and use information is even more important than it ever was, and without those basic building blocks and skill set you are way behind. Unless you can learn things quickly and apply them, and not be intimidated by people that can, it’s a real disadvantage, more than it was before,” he says.

  “It’s just more and better, part of it is human nature. So say some guy has a ten-foot long jump, well, people are going to try and jump ten feet and one inch. And so if you have the school and it’s competitive, people are gonna figure out better ways to get in and how to be more competitive, and the same thing with college, people are trying to get in and do more and more and be more competitive. Everybody’s trying to get an edge.”

  There are times when Chris wants to change course—or at least slow down a bit—though it doesn’t seem possible. “I feel out of alignment, I feel unbalanced, I feel like my outlook on life isn’t simple, I feel like it’s complicated. I don’t even feel all that disciplined,” he says. “Look, it’s all part of growing and existing. Who’s ever done this work, family, have a mortgage thing right?

  “Sometimes I wish you could work in a gas station and just be happy with being you and being alive. And it’s not OK. I can intellectualize it all I want and know that that’s an ideal but I’m pretty far from achieving that. I’m pretty affected by it.”

  “What do you mean?” I ask.

  “Just the need to achieve,” he says. “In part, it’s not just the family, it’s the whole culture. If you’re used to excelling, you either excel and you fit in, or you don’t. So sometimes it doesn’t feel like there’s a breather.”

  I tell Chris that I’m surprised, because from the outside—high school sports stardom, Princeton, good job, Mercedes in the driveway, beautiful house, loving family—he seems to be doing really well.

  “That’s what I’m saying,” he says. “My perception is different than that. It’s hard. It’s just the old saying, sometimes you need to stop and smell the roses. And if you’re always looking for a bigger flower, it’s … I’m not alone. I’m totally not alone. I think that’s not an unusual thing, when you grow up in an environment like that. And it’s not just my family, it’s Lakeside and that culture.

  “The higher your expectations are with everything, the tougher it is to reach them and therefore the tougher it is to be satisfied. It’s one thing I want to do and
it keeps shifting, it’s like the better you do or the more you have, you can catch yourself just focusing on the next thing, or comparing yourself against a different set of expectations.… But if you talk about spiritual development to me it means being able to just exist right now and be happy with what’s around me and not just focus on the future or the past or what didn’t happen, or what I want to happen, or what I don’t have. That’s jail, in my opinion. And a lot of times, it’s great. But it has its claws.”

  Lakeside Revisited

  On a Friday afternoon in September 2005, about three thousand students, parents, faculty, and alums of Lakeside School mingled under forty-eight tents set up on the school’s soccer field, browsing displays put up by school organizations such as the outdoor program, the athletic department, and the gay-and-lesbian student group. White banners around campus declared in cursive maroon script, LIVING OUR MISSION. A band played Brazilian music. Eventually the crowd filed into a large tent set with rows of chairs to listen to short speeches by students and alums leading to the main event, a keynote address by the school’s most prominent graduate, Bill Gates.

  The event marked the formal launch of a campaign to raise $105 million. That day, the school announced that the Bill & Melinda Gates Foundation had just pledged $40 million, and an additional $30 million in donations had already been lined up. The money, the school said, was being raised for two main purposes: to increase diversity by boosting the amount of financial aid available to students, and to expand the Global Service Learning Program, which would send students to places such as Peru and India to do volunteer work.

  Speaking from behind a podium, Headmaster Bernie Noe announced, “This evening we say to the families of the Greater Seattle area that if you have a son or a daughter who is qualified and motivated to do the work at Lakeside School, then we want your child to apply. We will make available financial assistance so that any child can attend the school.”