Surfers yelled at broadcaster Graeme Moody to free his leg rope as his surfboard was caught under rocks in 3m swells.
He was dragged underwater beyond the reach of onlookers.
When waves finally broke him loose, surfers paddled him ashore - but frantic rounds of CPR could not revive the Kiwi sports radio commentator and host.
Moody drowned while on holiday with his wife, Bev, at Angourie Beach, on the far north coast of New South Wales, where locals said he had been every year for up to 30 years.
The 60-year-old was a familiar face around town and was an experienced surfer - but he was caught in a "freak" accident, they said.
Angourie Beach is a cove about 500m wide, between two rocky points.
On days with high swells, experienced surfers walk up the rocks and jump off with their boards past the surf break, a shortcut of the long paddle from the beach.
As a veteran of Angourie Beach, Moody was doing the same just after noon on Wednesday, with four other surfers.
He jumped - but his board became trapped.
"He got stuck in probably one of the worst spots out there, at the break," said local surfer Craig Penman, who saw the tragedy and later pulled Moody from the waves and tried to resuscitate him.
It was a drizzly day in the tiny town, population 300, world-renowned for its surf but with only a single road leading into it.
"We tried to get to him because he was stuck underwater ... but we couldn't quite get there," Mr Penman said.
The president of the nearby Yamba Surf Life Saving Club, Alan Schofield, said witnesses had told him of the "very sad" incident.
"He jumped out at the wrong point and got pounded ... The others saw him and yelled to get his leg rope off - the board got wedged under the rocks," Mr Schofield said.
The waves eventually knocked Moody loose, and Mr Penman pulled him on to a board and paddled ashore.
The men took turns doing CPR on Moody as they waited for paramedics to arrive.
"We just continued to do it - it was a bit of a while... We tried to do the best we could. I wish we could've done more. But it's one of those unfortunate things," Mr Penman said.
"He was caught in the wrong place and that was it."
Moody died at the scene despite the arrival of an ambulance.
He worked for The Radio Network in Wellington and was the voice of Wellington and All Blacks rugby for the best part of two decades.
He covered several Commonwealth and Olympic Games and many top events.
Among the many All Blacks tests he called was the famous first series win against the Springboks in South Africa in 1996.
He was Newstalk ZB Wellington's breakfast sports anchor at the time of his death.
Long-time friend and colleague Brian Waddle told Newstalk ZB he had known Moody for 47 years and their careers had followed similar paths.
"It [Moody's death] is just numbing, it's hard to believe," Waddle said.
"He loved his surfing, he spent a lot of time surfing.
"He also loved his rugby; he was a great rugby player as well.
"And he loved his wife. Those were the three passions of his life."
Waddle said Moody had a gift for broadcasting, and he had never known him to receive any abusive emails or text from listeners.
"He was respected - his opinion was listened to," he said.
The Radio Network's talk programming general manager, Dallas Gurney, said Moody's death was a shock for the company and especially the tight team in Wellington.
Colleague Matt Brown said Moody "will be sorely missed as a friend and colleague and as the best rugby commentator out there".
Radio Sport morning broadcaster Tony Veitch told listeners Moody "had a rockstar look to him", and paid tribute to the broadcaster on Twitter.
"Radio Sport has lost one of the good buggers," Veitch wrote. "My thoughts with the family of Graeme Moody. You will be missed ..."
Wellington Classic Hits broadcaster Camille Guzzwell wrote on Twitter that Moody was "an incredible broadcasting legend with a wicked sense of humour who will be sorely missed. RIP Graeme Moody."
Listeners also used Twitter to give their tributes.
"Terribly sad news that Graeme Moody has passed away," Mark Shaw wrote. "A champion rugby commentator who introduced me to the game. RIP."
- Additional reporting: Paul Harper
Kiwi radio star 'in the wrong place'
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