If you know Jimmy, then you know tends to be a tad full of himself. He’s always posing shirtless for photos, and boasting about his latest triathlon P.R. (personal record).

“I bring it!” he’ll say. Or “Kim, you’re over your skis with me!” And of course, his trademark flex/brag combo, “Have you ever seen a 49-year-old this yoked?”

Recently something terrible happened. Jimmy turned 50. And like Ethan Hunt’s tape, his ego was dangerously close to self destructing.

It was time for a MISSION IMPOSSIBLE.

Tanner & Saxon threw down the gauntlet… “Yo bro, you need to catch 50 waves for your 50th b-day.”

“Fiddy for fiddy?” he asked. “BRING IT!”

So, Jimbo hopped a plane with his over-her-skis wife (me!) and two teenage sons and headed to Cabo to try and reach his goal of catching 50 waves in 3 days.

Our hotel of choice, Cabo Surf, was located in front of a surf break called “Old Man’s”—how perfect is that?

As soon as we checked in, Jimmy was on it! He slipped into hibiscus print board shorts. No wetsuit necessary—not when the water was a balmy 73 degrees. Just a thin rash guard to prevent chaffing.

Cabo Surf is home to the Mike Doyle Surf School. Along with co-inventing the boogie board, Mike was a champion surfer and paddler in the ’60s. He hung in Malibu with the original Gidget gang. We kept our eyes peeled for him from the get go.

That first afternoon was windy with texture on the water. Jimmy easily caught 10 waves—1/5 of his quotient. “Not much competition,” he sniffed. “Frankly, I’m more ripped than all these young bucks a quarter my age.”

 

With only 36 nicely appointed rooms, the Cabo Surf has an intimate, laid-back feel. Boards are propped against banana trees and cocopalms, and from dawn until dusk there’s a constant trickle of guests, boards tucked under their arms, cruises across the grounds headed for the sea.

On our first day, I awoke at 8 to find Jimmy’s side of the bed empty. Seconds later he came into the room dripping saltwater, clad in his rasta board shorts which perfectly reflected his chill mood. He’d dawn patrolled it, notching another 5 waves in his surf wax case. He was up to 15, and feeling quite confident. “There was some ‘Ed’ wearing lame reef booties trying to snake me, but I shut him down,” Jimmy boasted over huevos rancheros and gluten free French toast at 7 Seas, the hotel’s open-air restaurant.

After breakfast we headed out for a family surf sesh. It was relatively uncrowed—there were beginners taking lessons, local chicks who ripped, and assorted groms. The vibe was mellow and the break has multiple take off points. Unlike other more punishing spots, Old Man’s has a steep wave, but wipe outs are soft and forgiving.  We caught tons of fun party waves.

After a few hours, we took a break. Twenty-three waves in, Jimmy gloated, “I could have caught way more, but I was in instructor mode with you guys.”  Thanks, dude.

We were kicking back on the beach reading our books when we noticed Jimmy’s ripped six-pack was looking more like a seven-pack.

“Dad! It looks like you have a tumor!” Saxon grimaced. Turns out all that board-on-bone contact caused Jimmy’s previously broken rib, an old surf injury, to become inflamed. We started calling him Frankenstein Rib, Frankenrib, then finally McRib for short.

 

After reading a few chapters and tossing around the football, Jimmy announced he was heading back out for another sesh, his 3rd of the day.

“McRib, you better chill!” we warned.

But Jimmy ignored us. “Oh yeah, you only wish you could be this studly when you’re 50,” he said.

 

By the end of our second day we still hadn’t seen Mike Doyle. He splits his time between SoCal and Cabo, but the supposedly the legendary waterman was in town. I wondered if we’d ever see him in the flesh.

Speaking of flesh, Jimmy accidentally squirted a wedge of lime meant for his happy hour cerveza on his chafed inner thighs. Which didn’t make him so happy. “Sh*t!” he yelled. “That hurt!” Hmm, I wondered.  Was the old man starting to crack?

 The next day was picture perfect. The ocean fanned out before us like a peacock’s tail in stunning shades of cobalt, turquoise and aqua. We had a dream session riding the soft, fun waves. Counting his dawn patrol and our family sesh, Jimmy’s total wave count catapulted to 37!

He had 13 to go. We were leaving the next morning. Who knew what the surf would be like? It could be flat, it could be blown out. McRib could not risk defeat, so he three-peated yet again, dragging himself out for a sunset surf. By the end of the day Jimmy had reached 47.

He came in utterly exhausted, self-medicated with three Modelos and a bottle of cab, and passed out.

He only had three waves left but I wondered: Could he make his goal? Could he bring it?

On our  last morning,  Jimmy stepped gingerly into his Greg Knoll-style black-and-white-striped jailhouse board shorts, a fitting choice as he was in a prison of pain. He shuffled across the room, elbows and knees raw burger, deformed rib protrudint like an angry pink beet. Speckled with blood, his thighs looked as though they’d been sanded with extra coarse paper. He was shark bait.

The teens and I paddled out with him in solidarity. The swell had definitely died down. Jimmy scrapped for one wave. Then another. 49! “Dad! One more to go!” Tanner hooted. Thirty minutes passed. The clock was ticking. From out of nowhere a set came barreling in, and finally Jimmy scored his 50th wave.

As we paddled in, we passed a man with piercing blue eyes, broad muscular shoulders, his big hands cupping the water like oars. Mike Doyle.

From the jacuzzi we watched Mike catch the longest, most effortless wave of our trip. Glding gracefully across the bay, he cross stepped up and down his board from tip to tail, looking every bit surf royalty at 73 years old.

“Oh man! I’m gonna bring it like Mike when I’m 73,” Jimmy boasted.

Jimmy may have a broken rib but his ego will remain invincible until the end of time.