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Sailor · 2015–2025

James O'Leary

edgewater yacht club 420EnsignHandicap

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Events
30

171 races · 4 race wins

Win rate
3%

3% win rate · 1 of 30

Podium rate
7%

2 top-three finishes

Typically beats
39%

of boats faced (range 36%–41%, 1,060 boats)

Best class ranking
#798

Crew in 420 · rating 113

Longest win streak
2

race wins in a row

Most successful partnership
Hayden Clary

1 wins · 1 podiums in 7 events together · 14% win rate

Biggest lift
Hayden Clary

+30 points of fleet beaten when sailing together

Longest-running crew
Melissa O'Leary

Jun 2021 – Aug 2025 · 10 events

Nemesis
Sherrie Desmond

8–65 head to head in 73 races

Rival
Sydney Lombard

19–28 in 50 races

Best day
13 Jul 2023

1-3-3-3-3 · 2023 Gibson Island Junior Regatta

Signature result
1st of 16

2023 Gibson Island Junior Regatta · 420 · 13 Jul 2023

Partnerships · 8 sailors

Most successful partnership: Hayden Clary — 1 wins · 1 podiums in 7 events together · 14% win rate
  • Melissa O'Leary · Chancer · Ensign, Handicap 10events 0 wins together · 0 podiums · 0% win rate · 3 of 64 races won Beat 15% of the fleet together(−39 vs. without) · best 5th · Jun 2021 – Aug 2025
  • Scott Opert · Scott Opert, SSAJuniors · 420, J/22 9events 0 wins together · 1 podiums · 0% win rate · 0 of 55 races won Beat 50% of the fleet together(+13 vs. without) · best 3rd · Feb 2024 – May 2025
  • Hayden Clary · 8104, 89, Hayden Clary · 420 7events 1 wins together · 1 podiums · 14% win rate · 1 of 34 races won Beat 64% of the fleet together(+30 vs. without) · best 1st · Jan 2022 – Jul 2023
  • Deanna McLaughlin · Chancer · Ensign 1events 0 wins together · 0 podiums · 1 events · 0 of 7 races won Beat 10% of the fleet together · best 10th · Mar 2024 – Mar 2024
  • Ann Martino · SSAJuniors · J/22 1events 0 wins together · 0 podiums · 1 events · 0 of 8 races won Beat 8% of the fleet together · best 13th · May 2025 – May 2025
  • Emily Julian · SSAJuniors · J/22 1events 0 wins together · 0 podiums · 1 events · 0 of 8 races won Beat 8% of the fleet together · best 13th · May 2025 – May 2025
  • Skyler Krinetz · SSAJuniors · J/22 1events 0 wins together · 0 podiums · 1 events · 0 of 8 races won Beat 8% of the fleet together · best 13th · May 2025 – May 2025
  • SSA Juniors · SSAJuniors · J/22 1events 0 wins together · 0 podiums · 1 events · 0 of 8 races won Beat 8% of the fleet together · best 13th · May 2025 – May 2025

Lift shows how much better this sailor finishes with that partner aboard.

Rating history

-257-48161202020212022202320242025Helm rating, all classesCrew rating, all classes

— Helm rating, all classes · - - Crew rating, all classes

Event history · 30

DateEventBoatClassRoleFinish
4 Aug 20252025 Ensign National Championship RegattaChancerEnsignSkipper27th / 30
20 Jun 20252025 Cleveland Race Week One DesignChancerEnsignSkipper6th / 6
11 Jun 20252025 EDGEWATER RACE PROGRAMChancerEnsignSkipper6th / 7
2 May 20252025 Helly Hansen Sailing World Regatta Series - AnnapolisSSAJuniorsJ/22Spinnaker trimmer13th / 14
9 Aug 20242024 C420 South Shore ChampionshipScott Opert420Crew47th / 81
5 Aug 20242024 C420 US NATIONAL CHAMPIONSHIPScott Opert420Crew100th / 129
17 Jul 20242024 C420 Open North American ChampionshipScott Opert420Crew77th / 106
1 Jul 20242024 AYC Junior Annual RegattaScott Opert420Crew3rd / 27
30 Jun 20242024 Sandy MacVickar Junior RegattaScott Opert420Crew4th / 24
25 Jun 2024Club 420 Association New England ChampionshipScott Opert420Crew47th / 80
13 Jun 20242024 Cleveland Race Week One DesignChancerEnsignSkipper7th / 7
18 May 20242024 EYC Club Race ProgramChancerEnsignSkipper6th / 8
21 Mar 20242024 J-24 and E Scow Nor’easter & Ensign Midwinter RegattaChancerEnsignSkipper10th / 11
17 Feb 20242024 Club 420 Midwinter Championship for the John V. Hanson TrophyScott Opert420Crew94th / 148
2 Feb 2024Buccaneer Blast 2024Scott Opert420Crew4th / 27
8 Sep 2023Cleveland Cup 2023ChancerHandicapSkipper7th / 11
4 Aug 20232023 Ensign Region V ChampionshipChancerEnsignSkipper6th / 8
24 Jul 20232023 Club 420 North American ChampionshipHayden Clary420Crew114th / 130
13 Jul 20232023 Gibson Island Junior RegattaHayden Clary420Crew1st / 16
2 Jul 20232023 AYC Junior Annual Regatta Presented by Beasley Marine Inc.Hayden Clary420Crew6th / 25
17 Jun 20232023 Cleveland Race Week One DesignChancerEnsignSkipper8th / 8
13 May 20232023 EYC Club Race ProgramChancerEnsignSkipper5th / 7
1 Jan 20232023 Sandy MacVickar89420Crew7th / 22
14 Jul 20222022 Junior RegattaHayden Clary420Crew10th / 27
5 Jul 20222022 AYC Junior Annual RegattaHayden Clary420Crew16th / 33

Crew rating across all classes: -38, #49,846.Helm rating across all classes: -152, #77,167. Compiled from public results; not an official ranking.