Paddling a one-person outrigger canoe that he built himself, Conner won top honors in the Altres King Kalakaua Regatta from Magic Island to Honolulu Harbor.
''The race may have lacked big waves but the headwinds, particularly those winds found inside Honolulu Harbor, were fierce,'' said Conner, 52, after his one-hour, 17-minute and 55-second effort over the 10-kilometer course.
The veteran paddler passed paddleboarder Jackie Muller one-half mile from the finish.
In winning, Conner, an 11-time steersman of the Molokai Hoe, overtook all early-starting craft while holding off potentially faster canoes and surf skis.
In addition to his overall handicap victory, Conners also won the canoe masters' title.
The all-comers handicap festival drew 130 watercraft, consisting of surf skis, one-paddler and six-paddler canoes, sailing outriggers and paddleboards.
The fleet began in waves, based on estimated speed. Courses of five, 10 and 15 kilometers, fronting Waikiki and Honolulu, were used.
''I led the entire fleet until Tommy (Conner) passed me inside the harbor,'' said second place Muller after her 1:19:41 finish over five kilometers.
Though second in fleet standings, Muller still won the women's paddleboard crown.
''A hard but fun race,'' she said.
Dale Hope, paddling a one-person canoe, finished third overall in 1:19:44.
With its mix of boats, handicap start and assortment of courses, the regatta was more of a happening than a serious competition, with Aloha Tower Marketplace the regatta's headquarters.
''A non-serious competition - just the ticket for stress relief after a long hard racing season,'' said Lanikai Canoe Club's Kalani Irvine of yesterday's festive event.
Lanikai, last season's state regatta champ and Molokai Hoe winner, could manage no higher than fifth place yesterday.
Kailua Canoe Club's Rebels, winner of the women's six-paddler canoe division, dedicated the race to its steerswoman, Loretta Toth, who's moving to Hilo.
''We'll miss Loretta. She guided Kailua to many victories, including this one today,'' said crew member Makanani Wong.
Kailua, with a 1:22:11 finish, beat second place Wizzard Tamers by 2:38. Hui Nalu placed third among women, finishing in 1:25:42.
Kailua's winning crew consisted of Lesline Conners, Danna Dambacher, Sonia Lambert, Cindy Nash, Wong and Toth.
Outrigger Canoe Club's men barely won over the Waikiki Beach Boys, finishing in 1:23:06, just 19 seconds ahead.
The race was held over 15 kilometers.
''We pushed hard,'' said OCC's Marc Haine. ''Our goal is to get Outrigger back on top. This win represents a start.''
The Outrigger crew consisted of Bruce Black, Wyatt Jones, Todd Payes, Mark Sandvold, steersman Heath Hemmings and Haine.
Mahealani Lum, a Kamehameha Schools senior, topped the women's surf ski race, turning the 10 kilometers in 1:20:25.
''Headwinds nearly all the way,'' Lum said with a sigh.
John Puakea of the Hawaii Canoe/Kayak Team topped the men's surf ski division in a boat he designed and built.
''Wind in your face. A tough race,'' said Puakea, who completed the 15K in 1:22:55.
Roger McKeague, a one-person outrigger canoe participant, didn't win a medal or trophy yesterday, but because of his courage and seamanship, he won the hearts of spectators.
''Shortly after the Magic Island start both my Iakos (the carbon-fiber tubes which attach the hull to the ama, or float) cracked slightly,'' he said.
The spunky Lanikai Canoe Club paddler proceeded in the race hoping that the fractured tubes would hold.
''The tubes finally snapped in half just inside Honolulu Harbor,'' he said. ''But I wasn't about to quit.''
After anxious minutes he finally maneuvered his disabled craft across the finish line.
''And I didn't come in last,'' McKeague said, proudly.