Dazzling Blue #137: Life Lessons with Jeannie Chesser

Dazzling Blue #137: Life Lessons with Jeannie Chesser


Jeannie Chesser knows all about the highs and lows of life. Raised in Florida, she married her high school sweetheart, David. When David was nineteen and Jeannie was seventeen they had a son, Todd. For two years they lived what Jeannie called the “perfect life”—they worked to make ends meet, but mostly they surfed. While one played with baby Todd in the shorebreak, the other paddled out and rode waves.



            In 1970 David was killed in a car accident on a Miami freeway. Jeannie was shattered. “We’d only just gotten started,” she told me. Inspired by the surf film Five Summer Stories, she decided to take her boy and move to Hawaii. She knew no one, but she believed that surfing would heal her. 

            Things fell into place. She found a cheap house to rent in Kailua and a job airbrushing surfboards. Every morning she surfed Ala Moana Bowls, where the locals embraced this brave, vivacious twenty-four-year-old widow who danced across the punchy lefts. She entered contests and soon became one of Hawaii’s top-ranked female surfers.



            Todd followed in his mother’s footsteps. He surfed his first contest, the Haleiwa Menehune Meet, when he was five. I remember seeing his picture in Surfing: a cherubic blond with airplane arms flying across a tiny wave. Before long mother and son were bringing home twin first place trophies from weekend contests. 



            I became friends with Todd and Jeannie in the late ‘80s, and used to stay with them during summer contests. Their spartan three-bedroom home near Diamond Head oozed surfing. Jeannie’s airbrushed canvasses of perfect waves adorned the walls. Blazing Boards, Mad Wax, The Performers, and a host of other surf videos played nonstop on the TV. The bedrooms overflowed with boards, trophies, rash vests, bikinis, and wetsuits. In the carport, a surf leash doubled as a clothesline.  



            Surfing with mother and son had its own rhythm. In Jeannie’s blue Toyota pick-up, under a glaring South Shore sun, we cruised from spot to spot, where Todd and Jeannie bantered with dripping wet surfers in a heavy, clipped pidgin that I could not decipher. At Kaikoo’s, a surf spot hidden from view by million-dollar homes, we literally leapt from someone’s backyard wall into the crashing surf. 

            Todd and Jeannie came alive in the water. They knew every nook and cranny of the reef. They cooed each other into waves; exchanged codified nods and grunts. Jeannie tore off the bottom and banged lips. Todd’s style was not the textbook contest approach, but more stately, more Hawaiian. In hot pink board shorts, he swooped elegantly across the bright blue walls, his head bobbing as if to music.



            Todd would go on to become one of Hawaii’s greatest surfers. After mixed results on the ASP World Tour, he found his place in the big wave realm. He loved the outer reefs. Hated jet-skis. With a couple of close friends he rode spots that were barely detectable from shore. Then, on February 13, 1997, during a giant winter swell, Todd died while surfing his beloved Alligator Rock on the North Shore. He was 28. His passing sent shock waves throughout the surf world.



            Today, Jeannie, 71, lives near Diamond Head, sprays boards, makes art, and surfs nearly everyday. In celebration of International Women’s Day—and because I just love talking to her—I gave her a call and asked her to reflect on her storied life. Here’s an edited version, Jeannie on love, survival, and what matters most.



Surfing has given me peace of mind. It’s given me many boyfriends. It’s given me a son. It gives me a reason to wake up in the morning.


On the mainland, everybody is so ambitious—they want to get the nice house, the nice car, make a lot of money. But here in Hawaii you can catch fish and survive that way. You can live simply.


I saw the movie Blue Hawaii in the movie theater 13 times when it first came out in 1961. It resonated with me, and it inspired me to move to Hawaii. Of course I was in love with Elvis Presley—who wasn’t? But the way that Hawaii was portrayed was so real and beautiful, and I couldn’t wait to get here.


The first person that I met out at Ala Moana Bowls was Gerry Lopez, and that was the one person that I wanted to meet in my whole entire life because I saw the Surfer magazine poster of him at Ala Moana, and I thought, ‘That’s where I want to surf, and I want to meet this guy.’ I met him and I ended up surfing with him out there all the time.



Todd was on a board in Miami when he was barely two years old. Then, after my husband David died, I moved to Hawaii, and that’s where Todd started surfing seriously. I wanted him to have fun. We won lots of contests together. We were both in the Pro Class Trials one year—Todd was 14 (one of the youngest guys in the trials) and I was 33. I’ll never forget that.


There weren’t a lot of girls in the surf when I started, and I enjoyed that because I’d rather surf with guys than girls anyway. I was often the only girl out. And I surfed a lot with Rell (Sunn), who was my best friend. We’d go to Makaha and I’d get any wave I wanted when she was there, and when Rusty Keaulana was there. Those were great times.


It took me years to come to grips with Todd’s death. Surfing helped. Going to Tavarua helped. And all of Todd’s friends were right there for me. Also his sponsors, new and old, came to my aid financially. It was heartwarming. I didn’t realize that after 20 years I had never come to terms with Todd’s dad’s death. Since I had Todd to concentrate on, I’d swept that under the rug. Therapy revealed that to me. I learned so much.



I’ve had cancer twice now. The last time was right before my 69th birthday. I was going to have a big party, and then there I am in the hospital room, getting this lump taken out of my breast, and I’m telling the nurse, “Hey, today I’m 69, man. I want to go celebrate!” And she’s laughing at me. You’ve got to have a sense of humor. Because if you don’t laugh, you’re going to cry all day.


I’ve always liked to dance, and I love dancing, and I even dance by myself. If I’m at work and a good song comes on, I just start dancing to it. And I just like being active and I like surfing and I like that feeling of paddling when you just get your whole body into it. I’ve always been like that.


I look up to Bob Marley. I still just look up to Gerry [Lopez]. I look up to Benji Weatherley. I totally look up to Kelly [Slater]. He’s helped me so much. He bought me a Prius. He bought me that six years ago when he won the Pipe Pro. We were at the contest and I said, “Hey Kelly, if you win this contest, will you buy me a new car?” Because my truck had 289,000 miles on it. And he put his arm around me and said, “Sure. Whatever you want.” After the contest I called him and said, “Are you serious about getting me a new car?” And he said, “Yep. Dead serious. Go pick one out.” So I went straight to Toyota and picked one out. Kelly’s amazing.


Every once in a while I’ll come across a picture of Todd and I’m like, ‘Oh, shit.’ We had such a good time. He was such a good person. Surfing together was just a natural thing to us. I had him when I was so young, and I was still growing up, so we pretty much both grew up together.



We were like a big family, all of Todd’s friends, Ronald, Brock, Akila, Kelly, Seth, Pat, the whole crew. And we still get together on Todd’s anniversary day, and we have a breakfast at Café Haleiwa, and we go pour a beer out in his memory.


Biggest lesson I’ve learned is to try to be positive. If you’re feeling down, just go dancing or just dance around the house or do something physical. And try to laugh at yourself. Look at something funny, like your face in the mirror, and laugh.