MONTREAL (AP) – This was a stunner: Michael Phelps, exhausted and dangling on the lane rope, looking up in disbelief at the dismal time on the scoreboard beside his name.

Phelps arrived at the World Swimming Championships hoping to duplicate one of the greatest performances in Olympic history, the six-gold, eight-medal haul from Athens last summer.

Instead, he looked like just another swimmer the very first time he dove in the water in Montreal.

Phelps shockingly failed to qualify for the final of the 400-meter freestyle, fading badly after his last flip to wind up next-to-last in his heat and 18th overall in the preliminaries Sunday.

“Not the way I wanted to start off,” Phelps said. “It’s pretty disappointing. I felt good in the warmup, but then in the race, it wasn’t there.”

The morning swim is supposed to be a formality for someone of Phelps’ caliber, but he wasn’t even close to advancing on a warm, sunny day at Parc Jean-Drapeau. His time was nearly six seconds behind Australian star Grant Hackett and trailed the last of the eight qualifiers by more than 1 seconds.

With Phelps flopping and countryman Ian Thorpe skipping the meet, Hackett finally claimed a long-awaited victory in the 400. He was a runner-up to Thorpe at the last two world championships, as well as the Athens Olympics.

This time, Hackett coasted to the first swimming gold of the championships with a wire-to-wire victory. His relief was apparent when he popped from the water, spotted his winning time of 3 minutes, 42.91 seconds and thrust his right fist in the air.

Russia’s Yuri Prilukov took second, followed by Tunisia’s Oussama Mellouli. The lone American, Peter Vanderkaay, was sixth.

“Obviously, it’s a shame Michael wasn’t here today,” Hackett said.

Not that he felt too bad about it.

“He was in the race,” the Aussie said. “He just didn’t make the finals.”

Now, the most medals Phelps can win in Montreal is seven, and he’s got a long way to go before he can realistically challenge Hackett in the 400.

The 20-year-old Phelps looked fine most of the way, his long arms pulling him along at a comfortable pace, his large feet flapping in the water. He seemed content to hang right on the shoulder of the swimmer in the next lane, Italy’s Massimiliano Rosolino.

Then, approaching his final flip, Phelps began to labor. He turned for the finish in fourth place, knowing he needed to make up ground. But there was nothing left in the tank, three other swimmers going past him on the way to the wall.

When Phelps finally touched, the crowd gasped. He followed his usual routine, grabbing the rope and looking back at the scoreboard, but this time as a beaten man, not a triumphant champion.

Only one other swimmer in the heat was slower than Phelps over the last 50 meters.

“I was shocked when they came off the wall and left him,” said Bob Bowman, Phelps’ coach.

Hackett wondered if Phelps had been training long enough for the 400 – one of two new events the American took on for the world championships.

“His specialty is not the 400 and he probably needs more time,” Hackett said.

Phelps wanted to duplicate his medal count from Athens, qualifying for five individual events and expecting to swim the three relays. But this was never going to be Athens all over again.

Looking to take his program in new directions leading up to the 2008 Beijing Games, Phelps dropped two of his world-record events: the 200 butterfly and 400 individual medley. In their place, he picked up the 100 and 400 free.

The gamble backfired right away. Bowman said it’s probably been five years since Phelps failed to advance from a morning heat.

“I don’t think you can write off a whole meet just because of a preliminary swim,” the coach said.

Phelps still had a chance for his first medal, swimming in the evening finals as part of the 400 freestyle relay team. Without him, the U.S. put up the top time in the prelims, 3:16.04.

“I’ve got to step up and hopefully be better than this,” Phelps said. “I’ve got to put this behind me.”

South Africa’s Roland Schoeman set the first world record of the meet in the semifinals of the 50 butterfly with a time of 23.01. American Ian Crocker was second-fastest in the semis at 23.32.

France’s Laure Manaudou barely avoided the same fate as Phelps in the women’s 400 free prelim. The defending Olympic champion claimed the eighth – and last – spot in the final at 4:11.46.

Manaudou was more than three seconds slower than the top qualifier, Canada’s Brittany Reimer at 4:08.28. The two Americans, Carly Piper and Kelsey Ditto, did not advance.

The men’s 100 breaststroke is shaping up as another memorable showdown between world-record holder Brendan Hansen of the United States and Japan’s Kosuke Kitajima, who beat Hansen for the gold medal in Athens.

Kitajima set a meet record in the prelims at 59.71, edging the mark he set two years ago in Barcelona (59.78). Hansen was right behind at 59.84.

“I definitely held back,” Hansen said. “I definitely feel confident about the way I swam.”

Kitajima knows what he has to do.

“I need to break the world record to win the race,” he said, already looking ahead to Monday night’s final.

Australia’s Jess Schipper set a meet record in the prelims of the 100 fly, then broke it in the evening semifinals at 57.75. The previous mark was set two years ago by now-retired American Jenny Thompson.

Sixteen-year-old American Katie Hoff appeared to be the swimmer to beat in the 200 IM, posting the fastest times in both the preliminaries and semifinals.

Her evening swim, 2:11.71, was nearly two seconds faster than the closest swimmer, Zimbabwe’s Kirsty Coventry, a three-time medalist in Athens.

As expected, world-record holder Australia set the preliminary pace in the women’s 400 free relay at 3:40.57. The U.S., saving five-time Olympic medalist Natalie Coughlin for the evening final, settled for the fifth-best time.

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