SPORTS PSYCHOLOGY & FIGHTING FOR A FRIEND: BEHIND DOLAN’S MOLOKAI VICTORY
It’s impossible to miss how much Pat Dolan’s Molokai Challenge victory means to the Hawaiian paddling community.
When The Paddler spoke with the newly-crowned champion in the hours after his drought-breaking triumph, Dolan was the centre of celebrations at a friend’s house down the street from his home. The festivities loud enough that he had to step outside.
Harder to capture is just what winning means to Dolan himself.
The 37 year-old father-of-two is the first Hawaiian to claim the iconic crossing since Kalai Handley in 1978. And, Dolan did it in a record time for this current course.
He is also the first paddle to win both the surfski and OC1 Molokai titles.
On Sunday night, sitting on that verandah, the magnitude of his achievement was only just beginning to materialise.
“I don’t think I’ve processed it yet,” Dolan said. “But I have visualised and thought about this moment for so long.”
“As much as it means to me, I just hope it means something to Hawaii and can lead to bigger things for paddling here.
“We’re a small island community. I hope the kids can take something away from this.
“Dream big and work hard.”
Community is the pillar of Hawaiian culture. And it’s what Dolan credits for carrying him to the Molokai title.
It was Dolan’s grandfather who introduced him to outrigger paddling. The memory of watching Lanikai Canoe Club win the six-man Molokai Hoe in 2000 as a wide-eyed 11 year-old is still fresh in his mind. Dolan credits that day for inspiring his Molokai journey.
Pat’s first crossing came on his OC1 in 2004, aged just 15.
“OC1 and surfski used to be in the same race. Learning about Oscar [Chalupsky], learning about Dean [Gardiner]… that’s what got me interested in surfski paddling and kayaking.
“From there, it became a dream.”
As much as he loved paddling surfski, Dolan didn’t complete his Molokai on the craft until he was in his 20’s. And, extraordinarily, he almost picked up a podium in his first attempt in 2013.
The ocean, however, had other ideas. His ski snapped in three, after he was taken out by a wave at China Wall.
A 16th place in 2015 was followed by a sixth in 2017. In 2018, he was fourth.
The following year, he finally stood on the podium in third, alongside Hank McGregor and Cory Hill. In a stacked field, he was just one and a half minutes behind McGregor’s record-breaking time – and ahead of some of the sport’s biggest names.
The annual crossing was often the only time the surfski world would see Dolan compete, however. The outrigger was still the centre of his sporting season. And his commitment to that campaign was rewarded.
Last year, after a lifetime spent around the sport, Dolan claimed his first OC1 crown. It was a result he described as a “dream come true.”
Two weeks later, he was back on the Channel of Bones in his surfski.
And at the 25 kilometre-mark, found himself locked in battle at the front of the field with Cory Hill.
But from that point of the race, Hill put more than four minutes into Dolan, powering towards his fourth title.
The Hawaiian knew that if he ever wanted to add his name to surfski’s most-revered list, something had to change.
So, after discussions with his team, which includes the likes of 2-time Molokai 2 Oahu paddleboard champion, Australian Brad Gaul, Dolan chose not to defend his OC1 crown in 2025.
“I knew it was what I wanted, so I made that decision early to focus on the surfski race,” he said.
“As good as the conditions were for the OC1 crossing last year, I found it hard to recover. It’s like doing two marathons two weeks apart.
“It became harder and harder this year as the OC1 race came closer, especially watching the conditions they got.
“But it was all about putting myself in the best condition for today.”
There were other motivations, too.
Dolan describes Kai Bartlett, the creator of outrigger and surfski manufacturer Kai Wa’a, as “a family member.”
A five-time Molokai OC1 champion himself, Bartlett is currently battling cancer. His strength in the face of adversity has driven and inspired Dolan.
“He’s been my mentor since I started,” Dolan said. “He’s the one who picked me up and gave me a chance.
“I don’t think he was putting much thought into what helping me with a boat and everything could do.
“But he gave me a chance and that was the spark for me. I took that to heart very seriously and it’s the reason I’ve trained so hard.
“What he has done for me has driven me to this accomplishment. I wouldn’t be here without him.”
“It’s a special relationship. I think of him as a family member. And this all came from him offering to support me as a 15 year-old.”
“He’s always been the best mentor to me and I hope I can pay it forward and be a mentor to other guys.”
“He has been my motivation over these last few years.”
The size and depth of the field for the Molokai Challenge is down compared to a decade or two ago, but at the very front, the quality still stands tall.
Australian Cory Hill returned this week searching for his fifth race victory. That’s a number only achieved by three paddlers – Oscar Chalupsky (12), Dean Gardiner (9) and Grant Kenny (5).
Clint Robinson, who boasts three titles, also returned to the iconic race this year, while Danielle Richards provided a world-class presence in the women’s line-up.
The fleet of 22 surfski paddlers and 117 OC paddlers, either competing solo or in teams, were greeted by ideal conditions for the gruelling 52 kilometre crossing.
With the trees on Molokai blowing well before the start, paddlers were aware that the race would be fast.
But even so, after a lightning start of his own, defending champion Hill couldn’t believe his eyes an hour in – Dolan was out in front.
“I was actually a bit shocked that I wasn’t in the lead.” Hill said. “Until then, I thought I was going really well.
“Honestly, that hasn’t happened in recent years. I’ve always been aware of where people are, and I knew he was on a really good line as well.”
Dolan and Hill had broken away from the field, and even at this early stage, it was clear that this would be another race-in-two.
Hill began to chip away at Dolan’s lead, and by 25 kilometres – the halfway point of the course – they had drawn level.
To this point, the race was almost identical to 2024.
But 12 months on from the disappointment of how that day finished, Dolan was now armed with a new weapon.
Belief.
Together with his wife Angie, who is studying sports psychology, Pat had put in the work to mentally prepare for this exact moment.
“In the past, with all of the good guys that have come – especially Cory and Hank [McGregor] – I’ve almost been starstruck and just happy to be in their presence,” he revealed.
“I had to really change that mental thought to, ‘No, I deserve to be here and I deserve to challenge them.’
“Even starting with the pre-race jitters, it’s just about reframing that. It’s not anxiety, it’s preparation for what you’re about to do.
“I have so much respect for Cory, what he’s done for the sport and what he’s done for the Molokai race… I hold him in such high regard. But when it came time to compete, I had to see myself as an equal, and having an equal shot at winning.
“I felt like it was more of a mental race than a physical race for me. Just believing in myself and keeping strong.
“Honestly, that was what took me over the edge. But it was also the hardest thing to do.”
Although the field isn’t the same size as its heyday, the battle that unfolded over the second half of the race should go down as a Molokai classic.
“It was blow-by-blow, run for run.” Hill recalls.
“The last 10-15 kilometres were just nuts.”
Hill’s GPS data tells the story best.
From the 26th kilometre onwards, the second half of the race, he did not clock a single one-kilometre split slower than 3 minutes and 30 seconds until he was inside China Walls at the finish.
“It’s amazing, I’ve had it before in the Doctor with Hank where you’re just putting down fast times but look to your side and they’re still right there.” Hill said.
“I tried my best to, I guess, kill him,” he laughs. “But I couldn’t put him out. He kept fighting back and fighting back.”
Dolan claimed a small lead at China Walls, but Hill was right on his tail. The gap, no more than 25 metres.
The pair took slightly different lines, but no waves would change the lead. And once they hit flat water, Hill wouldn’t be able to reel the lead back in either.
Dolan crossed the finish in a record-breaking time of 3 hours, 9 minutes and 44 seconds to become the first Hawaiian in 46 years to win surfski’s most well-known race.
Hill was just 35 seconds behind him. That winning margin is the smallest since Hill finished 34 seconds behind McGregor in 2019.
South African Tyron Maher (3:23:29) claimed third, ahead of Clint Robinson (3:24:42) and Davey Brand (3:26:56).
Danielle Richards finished sixth overall to win the women’s crown in a record-breaking time of 3 hours, 33 minutes and 54 seconds, to add the iconic title to her list of achievements, cementing her status as one of the sport’s all-time greats.
The Paddler will catch up with Richards in the coming days to reflect on her race win.
Shivani Goberdhan (6:13:10) was the only other female solo surfski paddler in the event.
To view the full results of the 2025 Molokai Challenge, click here.
While the rest of the surfski world immediately celebrated Dolan’s triumph as one of the feel-good stories in recent racing, the man himself is still trying to make sense of it.
“Just that joy, that feeling of achievement, and being Hawaiian,” he reflected. “That gratitude for the tribe.
“That is my family, but also the surfski paddlers here in Hawaii. Some have passed, but they all mean the world to me and I have looked up to them… I just have so much gratitude and thankfulness for being able to race, and also having the ability to win.”
As Dolan stood from his ski on Oahu, he was greeted by a huge turn-out of family, lead by his wife Angie and his two children; Decklan, aged 5, and Teagan, aged 4.
“I owe it all to them,” Dolan said.
“I’m not sure how much my daughter took in, but there is a connection with my son there.
“My OC1 win and now today, I’m trying to set the tone for him. I want him to dream big. I want them both to dream big. And also just have that ability to put their heads down and work, and keep on going.”
“This has been a long journey for me. I’m 37 now, and this has been a dream since I started watching the surfskis coming across the line from Molokai.
“It’s been a 20 year process where I’ve just continued to chip away and keep up the hard work… and just believe.”
Also front of mind, his mentor Kai.
“He was actually escorting an OC1 relay team, so I was able to get him on the phone and share the news with him.
“We enjoyed some tears together and then when we came in I could give him a big hug.”
Dolan’s reflections again drift back to his adversary, Hill.
In a time of great change for the Molokai Challenge – persevering through COVID, dropping participation and changing sponsorship – Hill’s attendance has been a constant.
“I look up to Cory so much, he’s such an amazing champion.” Dolan said.
“I can’t thank him enough for continuing to come and support this race. The race has been getting kind of thin, but he has kept it legitimate.”
That sentiment is shared between the two.
“As a fan of the race and of the sport, it’s cool to see these fairytale results.” Hill said. “Whether it’s a German [Gordan Harbrecht] winning the World Championship in Europe, or a Hawaiian winning Molokai in a record time.
“I’m glad that I was here to be a part of it and give it my best shot. Sometimes you come up short and that’s part of being human.
“That doesn’t make it hurt less, but when I did cross the line… it was just so cool to witness the local boy winning and be part of that moment.”
“We’re both the same age, we both have kids and live similar lifestyles on different sides of the world.
“But we’ll be back again next year battling it out and see if we can break that record again.”
Before then, Dolan is eyeing off more surfski racing.
And at the top of the list is the Shaw and Partners WA Race Week.
“Dean [Gardiner] has always brought guys over to Hawaii, so it would be so awesome to have a Hawaiian contingent of young guys go there and get that same exposure.” He said.
“For me, there’s no real expectations. It’s just a bucket-list event to experience, so many surfski paddlers coming together. That would be so cool to share that with other Hawaiian paddlers.”
And for Dolan, that is what he hopes this record-breaking victory can deliver, above all else.
With the support of his own mentor Kai clear his mind, Dolan now wants to do the same to help continue Hawaii’s proud oceansports history.
“I hope there are young Hawaiian paddlers who, even if it’s not in surfski, can see that I set out to do something, worked hard, and achieved that goal.”
