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Sailor · 2010–2026

Ryan Dempsey

ayc Viper 640J/70J/80

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Events
45

288 races · 30 race wins

Win rate
16%

16% win rate · 7 of 45

Podium rate
33%

15 top-three finishes

Typically beats
51%

of boats faced (range 49%–54%, 1,164 boats)

Best class ranking
#22

Crew in J/109 · rating 447

Longest win streak
3

race wins in a row

Most successful partnership
Jay Rhame

2 wins · 3 podiums in 3 events together

Best trio
Jay Rhame & Peter Beardsley

2 wins · 3 podiums in 3 events, all three aboard

Biggest lift
Jay Rhame

+38 points of fleet beaten when sailing together

Longest-running crew
Cristina Filippelli

Oct 2010 – Oct 2022 · 7 events

Nemesis
Brian Keane

2–81 head to head in 83 races

Rival
Bill Sweetser

27–21 in 48 races

Best day
13 Jul 2016

2-8-1-1-8-1-10-11-1-1-1-5-2-6-3 · NYYC Race Week at Newport presented by Rolex - PART II - One-Design and Handicap

Signature result
1st of 25

2015 Storm Trysail Club Block Island Race Week XXVI · J/109 · 23 Jun 2015

Partnerships · 60+ sailors

Most successful partnership: Jay Rhame — 2 wins · 3 podiums in 3 events together
  • Mark Gorman · Caminos, Fox, Pazzi · J/109, J/70, J/80 9events 1 wins together · 2 podiums · 11% win rate · 7 of 62 races won Beat 48% of the fleet together(−19 vs. without) · best 1st · Jun 2015 – Oct 2022
  • Kenneth Nilsen · Caminos, Pazzi, Trailer Park Boys · J/109, J/70 9events 1 wins together · 4 podiums · 11% win rate · 11 of 77 races won Beat 60% of the fleet together(−4 vs. without) · best 1st · Jun 2013 – Sep 2018
  • Cristina Filippelli · Caminos, Fox, Gallant Fox · J/109, J/80 7events 1 wins together · 4 podiums · 14% win rate · 10 of 60 races won Beat 79% of the fleet together(+19 vs. without) · best 1st · Oct 2010 – Oct 2022
  • Matthew Nilsen · Caminos, Trailer Park Boys · J/109, J/70 7events 1 wins together · 2 podiums · 14% win rate · 7 of 59 races won Beat 53% of the fleet together(−12 vs. without) · best 1st · May 2014 – Sep 2018
  • Peter Ill · Caterpillar · Viper 640 6events 1 wins together · 1 podiums · 17% win rate · 4 of 52 races won Beat 75% of the fleet together(+14 vs. without) · best 1st · May 2023 – May 2025
  • Donald Filippelli · Caminos · J/109 6events 1 wins together · 5 podiums · 17% win rate · 13 of 48 races won Beat 85% of the fleet together(+25 vs. without) · best 1st · Jun 2011 – Jul 2016
  • Peter Beardsley · Glory Days, Great Scott! · Viper 640 5events 2 wins together · 4 podiums · 40% win rate · 6 of 23 races won Beat 92% of the fleet together(+32 vs. without) · best 1st · May 2021 – Aug 2024
  • Chris Buncke · Caminos · J/109 4events 0 wins together · 3 podiums · 4 events · 6 of 28 races won Beat 78% of the fleet together(+17 vs. without) · best 2nd · Jun 2011 – Jul 2016
  • Doug Stryker · MAYHEM, Pazzi, TOTALed MAYHEM · J/105, J/30, J/70, J/80 4events 2 wins together · 2 podiums · 4 events · 4 of 22 races won Beat 78% of the fleet together(+17 vs. without) · best 1st · Jan 2019 – May 2026
  • Brian Robinson · Caminos, Gallant Fox, Velvet Hammer, Zombie · J/105, J/109, J/70, J/80 4events 0 wins together · 1 podiums · 4 events · 2 of 25 races won Beat 70% of the fleet together(+8 vs. without) · best 2nd · Jun 2011 – Oct 2023

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

Rating history

-8221450201120142017202020232026Helm rating, full-size sailingCrew rating, full-size sailing

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

Event history · 45

DateEventBoatClassRoleFinish
8 Aug 2026Shelter Island Yacht Club - 2026 Race Week - Anniversary RegattaZinger had to workViper 640Alternate2nd / 10
1 May 20262026 Helly Hansen Sailing World Regatta Series - AnnapolisMAYHEMJ/105Other1st / 23
2 May 20252025 Helly Hansen Sailing World Regatta Series - AnnapolisCaterpillarViper 640Tactician5th / 18
3 Aug 20242024 Race Week at Shelter Island - Anniversary RegattaGlory DaysViper 640Skipper1st / 7
2 Aug 20242024 Race Week at Shelter Island - Around-the-Island RaceGlory DaysViper 640Skipper1st / 7
2 May 20242024 Helly Hansen Sailing World Regatta Series - AnnapolisCaterpillarViper 640Tactician4th / 24
4 Mar 20242024 Bacardi Cup Invitational RegattaCaterpillarViper 640Tactician10th / 22
20 Oct 20232023 J/24 and J/22 East Coast ChampionshipPainkillerJ/22Headsail Trimmer14th / 20
5 Oct 2023The British Virgin Islands 2023 J/105 North American ChampionshipVelvet HammerJ/105Other9th / 31
22 Sep 2023Viper 640 North American Championship Presented by BMO Private WealthCaterpillarViper 640Other5th / 23
26 Aug 202354th Lawrence I. Clarke Memorial 'Round Gardiner's Island RaceFoxPHRF handicapOther3rd / 6
27 Jul 20232023 Helly Hansen Sailing World Regatta Series - MarbleheadEvil HissViper 640Floater13th / 23
23 Jul 20232023 Outer Light ClassicBiancaPHRF handicapOther6th / 6
2 Jun 20232023 Southern Bay Race WeekCaterpillarViper 640Tactician1st / 11
5 May 20232023 Helly Hansen Sailing World Regatta Series - AnnapolisCaterpillarViper 640Helm8th / 14
28 Mar 2023Allstate Sugar Bowl 2023 Viper 640 World ChampionshipGreat Scott!Viper 640Tactician11th / 33
5 Oct 20222022 J80 World ChampionshipFoxJ/80Other24th / 48
27 Aug 202253rd Lawrence I. Clarke Memorial 'Round Gardiner's Island RaceFoxPHRF handicapOther1st / 5
13 May 20222022 Helly Hansen Sailing World Regatta Series - AnnapolisGreat Scott!Viper 640Tactician2nd / 23
5 Dec 20212021/2022 DIYC J 70 Winter Series 1 (2021 Midwinter)PazziJ/70Other43rd / 57
1 Oct 20212021 J/80 North American ChampionshipMAYHEMJ/80Other7th / 23
18 Sep 20212021 J-Jamboree - East Coast ChampionshipFoxJ/80Other5th / 21
22 May 20212021 Viper 640 Atlantic Coast ChampionshipGreat Scott!Viper 640Tactician2nd / 16
25 Jul 20202020 AYC Annual RegattaTOTALed MAYHEMJ/30Spinnaker trimmer1st / 4
9 Feb 20192018/2019 J 70 Winter Series 3PazziJ/70Other36th / 51

Crew rating, Full-size sailing: 450, #2,682.Helm rating, Full-size sailing: 167, #24,568. Compiled from public results; not an official ranking.