Skip to content

Sailor · 2010–2026

Richard O'Leary

bass river yacht club Beetle CatCollege keelboatHandicap

Search sailors · About these ratings

Events
66

286 races · 37 race wins

Win rate
3%

3% win rate · 2 of 66

Podium rate
32%

21 top-three finishes

Typically beats
53%

of boats faced (range 50%–57%, 565 boats)

Best class ranking
#57

Helm in College keelboat · rating 153

Longest win streak
2

race wins in a row

Most successful partnership
Tobias Ferl

2 wins · 10 podiums in 18 events together · 11% win rate

Best trio
Tobias Ferl & Gregory Gaskel

2 wins · 9 podiums in 12 events, all three aboard

Biggest lift
Chris Jinsei Alemania

+27 points of fleet beaten when sailing together

Longest-running crew
Tobias Ferl

Aug 2017 – Nov 2019 · 18 events

Nemesis
William Lawrence

11–34 head to head in 45 races

Rival
Christopher Dawson

28–20 in 48 races

Best day
28 Apr 2018

2-1-4-1-3-2-1-2-4-1-4-2-1-4-5-4-1-3-3-1-1-4-2-5-5-2-2-5-5-6-2-4 · Coast Guard J/70 Open

Signature result
1st of 7

J-70 Spring Open · College keelboat · 20 Apr 2019

Partnerships · 50 sailors

Most successful partnership: Tobias Ferl — 2 wins · 10 podiums in 18 events together · 11% win rate
  • Tobias Ferl · Glory, Jammy Beggar, U. S. Coast Guard Academy (Bears 2), U. S. Coast Guard Academy (Bears) · College keelboat, J/44, PHRF handicap 18events 2 wins together · 10 podiums · 11% win rate · 26 of 158 races won Beat 67% of the fleet together(+23 vs. without) · best 1st · Aug 2017 – Nov 2019
  • Megan Wadleigh · Coast Guard - Glory, Hedgehog, Jammy Beggar, U. S. Coast Guard Academy (Bears 2) · College keelboat, IRC handicap, J/109, J/44 18events 1 wins together · 9 podiums · 6% win rate · 14 of 132 races won Beat 58% of the fleet together(+10 vs. without) · best 1st · Apr 2018 – Mar 2020
  • Gregory Gaskel · Coast Guard - Glory, Glory, Jammy Beggar, U. S. Coast Guard Academy (Bears 2) · College keelboat, J/44, Melges 32 15events 2 wins together · 11 podiums · 13% win rate · 24 of 127 races won Beat 69% of the fleet together(+25 vs. without) · best 1st · Oct 2017 – Nov 2019
  • Liam Long · Coast Guard - Glory, Hedgehog, Polar, U. S. Coast Guard Academy (Bears 2) · College keelboat, IRC handicap, J/70, ORC handicap 12events 0 wins together · 4 podiums · 0% win rate · 5 of 88 races won Beat 52% of the fleet together(+2 vs. without) · best 2nd · Mar 2019 – Mar 2020
  • Eric Gimple · Coast Guard - Glory, Glory, Jammy Beggar, U. S. Coast Guard Academy (Bears) · College keelboat, J/44, PHRF handicap 11events 0 wins together · 4 podiums · 0% win rate · 8 of 81 races won Beat 57% of the fleet together(+8 vs. without) · best 2nd · Aug 2017 – Mar 2019
  • Zachary Groce · Coast Guard - Glory, Glory, Jammy Beggar, U. S. Coast Guard Academy (Bears) · College keelboat, J/44, PHRF handicap 10events 0 wins together · 4 podiums · 0% win rate · 8 of 72 races won Beat 59% of the fleet together(+11 vs. without) · best 2nd · Aug 2017 – Nov 2018
  • Jesse McKnight · Coast Guard - Glory, Hedgehog, U. S. Coast Guard Academy (Bears) · College keelboat, IRC handicap, ORC handicap, PHRF handicap 10events 0 wins together · 5 podiums · 0% win rate · 3 of 59 races won Beat 55% of the fleet together(+6 vs. without) · best 2nd · Nov 2018 – Mar 2020
  • Jake Dennis · Coast Guard - Glory, Glory, U. S. Coast Guard Academy (Bears) · College keelboat, J/44 8events 0 wins together · 2 podiums · 0% win rate · 8 of 66 races won Beat 56% of the fleet together(+6 vs. without) · best 2nd · Sep 2017 – Oct 2018
  • Jarred Gaudineer · Coast Guard - Glory, Hedgehog, Jammy Beggar, U. S. Coast Guard Academy (Bears) · College keelboat, IRC handicap, J/109, Melges 32 7events 0 wins together · 2 podiums · 0% win rate · 0 of 29 races won Beat 40% of the fleet together(−11 vs. without) · best 2nd · May 2019 – Mar 2020
  • Merrill Cline · Coast Guard - Glory, U. S. Coast Guard Academy (Bears), US Coast Guard Academy - Morning Glory · College keelboat, IRC handicap, J/109, ORC handicap 7events 0 wins together · 4 podiums · 0% win rate · 3 of 35 races won Beat 63% of the fleet together(+14 vs. without) · best 2nd · May 2019 – Mar 2020

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

Rating history

0154307201120142017202020232026Helm rating, full-size sailingCrew rating, full-size sailing

— Helm rating, full-size sailing · - - Crew rating, full-size sailing

Event history · 66

DateEventBoatClassRoleFinish
15 Aug 2026NEW ENGLAND BEETLE CAT BOAT ASSOCIATION LEO J. TELESMANICK CHAMPIONSHIPWilliam O'LearyBeetle CatCrew3rd / 12
8 Aug 20262026 Beetle Cat August SeriesLIMNERBeetle CatSkipper3rd / 6
11 Jul 20262026 Beetle Cat July SeriesLIMNERBeetle CatSkipper4th / 6
11 Jul 2026Irving K. Taylor Trophy RaceLIMNERBeetle CatSkipper6th / 6
9 Aug 20242024 Leo J Telesmanick ChampionshipSummer WindBeetle CatCrew15th / 23
24 May 20242024 Storm Trysail Club Block Island RaceCool BreezeORC handicapOther2nd / 8
12 Aug 20232023 Leo J Telesmanick ChampionshipLimnerHandicapSkipper14th / 23
6 Mar 2020Port of Los Angeles Harbor CupU. S. Coast Guard Academy (Bears)College keelboatA Crew8th / 10
11 Jan 20202019/2020 DIYC J 70 Winter Series 2PolarJ/70Other9th / 53
2 Nov 2019Kennedy CupU. S. Coast Guard Academy (Bears)College keelboatA Crew2nd / 9
19 Oct 2019McMillan Cup 2019U. S. Coast Guard Academy (Bears)College keelboatA Crew2nd / 10
12 Oct 20192019 Storm Trysail Club / Larchmont Yacht Club - Intercollegiate Offshore RegattaUS Coast Guard Academy - Morning GloryJ/109Helm4th / 9
14 Sep 2019Shields Trophy RegattaU. S. Coast Guard Academy (Bears)College keelboatA Crew3rd / 11
7 Sep 2019Pine TrophyU. S. Coast Guard Academy (Bears 2)College keelboatA Skipper6th / 7
7 Sep 2019Pine TrophyU. S. Coast Guard Academy (Bears 2)College keelboatA Skipper4th / 7
31 Aug 201963rd Fishers Island YC 'Round Island RaceJammy BeggarMelges 32Other3rd / 4
24 Jun 20192019 Storm Trysail Club Block Island Race WeekHedgehogPHRF handicapMain Trimmer8th / 15
15 Jun 2019165th NYYC Annual RegattaCoast Guard - GloryIRC handicapNavigator6th / 7
7 Jun 20192019 Annapolis - Newport RaceCoast Guard - GloryORC handicapNavigator2nd / 7
24 May 20192019 Storm Trysail Club Block Island RaceCoast Guard - GloryIRC handicapNavigator7th / 8
20 Apr 2019J-70 Spring OpenU. S. Coast Guard Academy (Bears 2)College keelboatA Skipper3rd / 7
20 Apr 2019J-70 Spring OpenU. S. Coast Guard Academy (Bears 2)College keelboatA Skipper1st / 7
8 Mar 2019Port of Los Angeles Harbor CupU. S. Coast Guard Academy (Bears)College keelboatA Crew7th / 10
3 Nov 2018Kennedy CupU. S. Coast Guard Academy (Bears)College keelboatA Crew3rd / 10
13 Oct 2018McMillan CupU. S. Coast Guard Academy (Bears)College keelboatA Crew4th / 10

Helm rating, Full-size sailing: 223, #16,702.Crew rating, Full-size sailing: 273, #9,461. Compiled from public results; not an official ranking.