Q&A: The Whittaker Brothers Share Lessons From Their Mount Kennedy Expedition

Bob and Leif Whittaker didn’t spend much time together while growing up in Washington. Eighteen years older, Bob left home around the time Leif was born to pursue a career in the music industry, eventually taking to the road as tour manager for alt-rock bands like Mudhoney and R.E.M. He was gone often and, aside from a few games of basketball, he and Leif didn’t interact much. But Leif said his older brother was almost like a heroa grunge-rock one who donned a leather jacket and rode a motorcycle. 

The brothers led very different adult lives, as well. While Bob embraced the alternative music scene, Leif became an author and mountaineer, twice summiting Mount Everest. But despite the distance and differences, the brothers say they always had a strong connection, one they immeasurably strengthened during their 2015 climb of Mount Kennedy in Canada’s Yukon—a journey that is now the subject of a new feature-length documentary, Return to Mount Kennedy.

Along with Christopher Kennedy, the brothers climbed to honor the first ascent of the nearly 14,000-foot peak, accomplished by their fathers—the late senator Robert F. Kennedy and Jim Whittaker, the first American to summit Mount Everest and former REI Co-op CEO. The 1965 climb helped establish a lifelong friendship between Robert F. Kennedy and Jim Whittaker. And in 2015, it helped Leif and Bob bolster theirs. The brothers spent a lot of time together organizing the ascent and filming their preparation for it. Together, they tackled the challenge of coordinating a climb in a remote part of Canadabalancing the needs of both a film crew and novice climbers like Christopher Kennedy. But they perhaps bonded most over a shared sense of humor—a self-deprecating one that is sure to invoke a few laughs among those watching the film.  

“We have that going on in each other,” Leif says of their comedic side. “But it brought us together. For me, that’s been the biggest benefit of the whole thing—just getting to know Bobby better, and the whole thing bringing us together.”

But there was more to the climb than deepening a brotherly bond. Here, Bob and Leif share why the documentary is different than other outdoor films; how Bob’s relationship with the outdoors has changed since his grunge days; and why people don’t need to summit a mountain to enjoy a life outside.  


Bob, the film really sets the tone of what your early life was like—from leaving home at 18 to working in the music industry. During those years, did you have a relationship with the outdoors? 

Bob: I always kept one foot in the outdoors. I was heavily into music and urban culture and the alternative music scene—punk rock, grunge, new wave—but I always sort of offset that by going to the Olympic Peninsula or to the mountains. I think that’s not uncommon in the Pacific Northwest. We’re pretty rooted in nature here. But I know a lot of my friends were all like, “Why do you always want to go on a walk?” or “Why do you always want to go in the woods?” So it perplexed some people. But it just made perfect sense to me.


Leif, what did climbing Mount Kennedy mean to you on a personal level?

Leif: To me, it’s really about the wilderness connecting people and time spent in the mountains together and how that forms bonds. And this wonderful friendship that was formed between my father and Bobby Kennedy really began there in the tent on Mount Kennedy on their climb. 

To go back to Mount Kennedy with my brother Bobby, who, while we knew each other growing up, was obviously quite a bit older than me. We weren’t super close. He was off doing his own thing. I think just the bond that we formed going through the whole expedition together—organizing it and making the film—has been the greatest benefit to me. 


There’s a quote in the film about how the outdoors can bring out the best in people. Do you feel that’s true for you?

Bob: I do. there’s something primordial about being out in the wilderness or staring at a fire on the beach or what have you. I would do that alone or with friends. It’s really cathartic, but also if you don’t do that, there’s really something missing, I think. You don’t have to go run around in the woods all the time, but you definitely gotta reach out and touch it once in awhile.

Leif: Yes, absolutely. I think that a connection with nature is essential to feeling healthy and balanced and rooted. And again, you don’t need to go climb Mount Kennedy or Mount Everest or El Capitan to feel that. You can just go on a walk in the park, even a city park, or in your backyard somewhere. 


Absolutely. Now coming back to climbing Mount KennedyBob, the film depicts some of your struggles training. What was the toughest part about preparing for climbing Mount Kennedy?

Bob: I really enjoyed the training because I hadn’t been doing that for a long time. Putting the goal of Mount Kennedy on the horizon helped me get out more and push myself more. Physically, I felt like that helped me. And mentally.

The biggest challenge for me in the training element was the high altitude. I just didn’t have the wind. Above 10,000 feet, I started struggling a lot. But you know, it’s a fun struggle [laughs].


What do you want people to take away from your story?

Bob: In my naivety, I was telling Leif, “We should bring a filmmaker because this family history is interesting.” But I also wanted to get my father’s message out about conservation and Bobby [Kennedy’s] message out about civil rights and human rights. 

But then the next thing I knew, Eric [Becker, the film’s director] kept asking me questions while the camera was rolling, and I was like, “Why the hell is he asking me all the questions?” And it sort of dawned on me that I’m going to be in a film. That was tough for me, and I fought it, and I didn’t like that. Then I gave in and went with it, and I think it’s a better film and a better story. But I still wish I was in it less [laughs].

Leif: I would hope that people came away from it feeling a sense of positivity and hopefulness toward the future and a sense of appreciation for the outdoors and the importance of these natural places that we all share. If those things could be accomplished, if it influenced some people to see the outdoors differently or to realize that, like I said, the hike out their backdoor is just as important as a free solo on El Capitan, then that would be a great achievement for the movie.

But it’s a complex story, and there’s a lot of different threads—political and artistic—and all sorts of things going on there. I think—and I believe this in writing, too—the main thing is to entertain people, and that’s probably true of film, as well. So thankfully Bobby is such an entertaining guy that he carries the torch in that regard. But I think it’s entertaining and moving. It chokes me up every time I watch it, so there’s that as well. 


Leif, what made climbing Mount Kennedy different from other climbs you’ve done?

Leif: One of the differences with Mount Kennedy is it’s so rarely visited. It’s this remote peak out in the middle of the Canadian Yukon that, because it’s not the highest or the most difficult, it doesn’t really attract a whole lot of climbers, and it’s very hard to get to. You can really only get there by helicopter or a ski plane lowered down on the glacier.

One thing for me that was a challenge was being the leader of that expedition and bringing together all these different elements: a film crew; a director of photography, Mikey Schaefer, who is a world-class mountaineer; and a person like Chris Kennedy who’s not accustomed to being in the mountains; nor is Bobby, my brother. So we had just this vast range of experience levels and skill levels to be responsible for. I’m more accustomed to being on mountains with people who are a little bit closer as far as their levels of experience go and their reasons for being there. So yeah, it was a challenge to bring all that stuff together, but it went relatively well, I think. 


Bob, going back to the conservation piece you mentioned earlier, why is this so close to your heart? Why is this an important message for you to spread through this film?

Bob: I worked in the music business for so many years, and even though I worked for some bands that were all wonderful, incredible, lovely people and some of them, like R.E.M., were so civic-minded and do so much for the community and are so progressive, it was still hard work. You come back, and you don’t really have anything to show. There was no real body of work to be proud of, for me, personally.

Between tours, I started giving back to the community, and that really enriched me and made me feel whole. That took the form of that rail trail in [Washington’s] Ferry County, and so that’s when everything started to click. I was so happy and so in my happy place working on that thing and giving back to communities and meeting new people. Even the struggles, which are many, I just really enjoy it. You’re part of something that’s bigger than yourself.


That’s a great message. Climbing Mount Kennedy was also very personal. How did climbing the mountain change how you see the outdoors?

Bob: I’ve been evolving my whole life I guess. I hope [laughs]. I’m becoming more conscious and more aware. In the early days, I would alternate between intense, urban, gritty culture and the wilderness. I used to go out there and run around on trails. I didn’t know that it took people working to preserve those areas as parks. It took grants and people working to make those trails. I was just going out there tromping around. And now I’ve evolved to understanding that advocacy. That’s the transition. It’s been a long, slow one, and I think it just escalated like crazy with Mount Kennedy.


Was there any part of your story you were nervous to share?

Bob: [Laughs] I never figured I was for public consumption. My narrative is a little rough. I do enjoy sitting in the back and people laughing at some of the jokes and some of the shenanigans. I’m painfully me sometimes, I guess. I never thought I was going to be 25 feet wide on a movie screen. That’s a bit much.

Leif: [Laughs] The whole time. The whole movie. The process of making the movie was obviously a lot longer than the process of climbing the mountain and filming most of the movie, so it’s been through many, many iterations. I’m still uncomfortable with some parts of the movie. I don’t think that’s rare for the subject of a documentary to feel. I think that’s probably really common, but at this point I think it is what it is. Eric had a story that none of us knew how to tell, and he did a fantastic job of bringing it all together.


This film is relatable too, I think. It’s not a film about super athletes, which is great because the outdoors isn’t about just one type of person getting out there.

Bob: I think it’s a nice film because you have all these different people. You have that dichotomy between Leif and I. Me flopping around up on that mountain with Leif being a pro was fun. The film will show people that [anyone] can go and run around in the woods and get their fill.

Leif: I think it’s perhaps a subtlety that will be lost on some viewers, but it’s funny. Climbing films and outdoor films in general tend to be very cliché. They follow this very, very common cliché structure of man versus nature or human versus nature. We wanted to do something that was a little bit different that was more relatable to everyday people who go out and have experiences outside. You go out on a bike ride in your backyard or a hike just in the Cascades, and you’re not pushing the boundaries of human endeavor, but that doesn’t make it any less valuable. 


Do you plan on checking off any other climbs in the future?

Bob: Hell no [laughs]. Just kidding. After we came down off of the mountain, the director said, “I know what we’re going to do. We’re going to go back and summit.” Leif and I just laughed at him. We were like, “We checked all the boxes on this expedition. We don’t have to throw a flag in the summit.” 

Editor’s note: Interview has been edited for length and clarity.

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