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Sailor · 2016–2026

Jamie Gregory

eastport yacht club J/30J/105Lido 14

Search sailors · About these ratings

Events
118

415 races · 44 race wins

Win rate
7%

7% win rate · 8 of 118

Podium rate
24%

28 top-three finishes

Typically beats
39%

of boats faced (range 37%–41%, 1,463 boats)

Best class ranking
#17

Helm in Lido 14 · rating 365

Longest win streak
5

race wins in a row

Most successful partnership
Eric Kessler

2 wins · 3 podiums in 10 events together · 20% win rate

Best trio
Eric Kessler & Sean Rogers

2 wins · 2 podiums in 8 events, all three aboard

Biggest lift
Avery Gregory

+23 points of fleet beaten when sailing together

Longest-running crew
Gregg Sunshine

Apr 2016 – Oct 2026 · 18 events

Nemesis
Dan Watson

30–131 head to head in 161 races

Rival
Heidi Frist

55–62 in 117 races

Best day
13 Jul 2026

3-4-5-1-2-2-2-3 · 2026 Lido 14 Class Championships

Signature result
1st of 10

2022 Liniment Regatta · Portsmouth handicap · 19 Nov 2022

Partnerships · 53 sailors

Most successful partnership: Eric Kessler — 2 wins · 3 podiums in 10 events together · 20% win rate
  • Gregg Sunshine · Dragonfly, Helios, One Love · J/105, J/30, PHRF handicap 18events 1 wins together · 2 podiums · 6% win rate · 3 of 74 races won Beat 38% of the fleet together(−5 vs. without) · best 1st · Apr 2016 – Oct 2026
  • Sean Rogers · Dragonfly, One Love · J/105, J/30 14events 2 wins together · 2 podiums · 14% win rate · 4 of 57 races won Beat 40% of the fleet together(−3 vs. without) · best 1st · Aug 2023 – Oct 2026
  • Scott Medeiros · Dragonfly, One Love · J/105, J/30, PHRF handicap 13events 1 wins together · 2 podiums · 8% win rate · 1 of 48 races won Beat 35% of the fleet together(−8 vs. without) · best 1st · Apr 2021 – Sep 2026
  • Avery Gregory · A Team, A-Team, ATeam, Jamie Gregory · Lido 14 13events 0 wins together · 5 podiums · 0% win rate · 6 of 70 races won Beat 63% of the fleet together(+23 vs. without) · best 2nd · Apr 2022 – Jul 2026
  • Eric Kessler · Dragonfly, One Love · J/105, J/30, PHRF handicap 10events 2 wins together · 3 podiums · 20% win rate · 3 of 25 races won Beat 46% of the fleet together(+5 vs. without) · best 1st · May 2025 – Sep 2026
  • Ben Lyon · One Love · J/30, PHRF handicap 9events 0 wins together · 0 podiums · 0% win rate · 0 of 36 races won Beat 29% of the fleet together(−14 vs. without) · best 4th · May 2021 – May 2023
  • Travis Paez · One Love · J/30 9events 0 wins together · 0 podiums · 0% win rate · 0 of 29 races won Beat 23% of the fleet together(−21 vs. without) · best 4th · Apr 2021 – Sep 2022
  • Courtney Winans · Dragonfly, One Love · J/105, J/30 6events 0 wins together · 0 podiums · 0% win rate · 2 of 36 races won Beat 18% of the fleet together(−25 vs. without) · best 4th · May 2024 – Sep 2026
  • Jennifer Moeller · Dragonfly · J/105 5events 0 wins together · 0 podiums · 0% win rate · 0 of 17 races won Beat 30% of the fleet together(−12 vs. without) · best 5th · May 2026 – Sep 2026
  • Emily Martin · One Love · J/30 4events 0 wins together · 0 podiums · 4 events · 0 of 14 races won Beat 28% of the fleet together(−15 vs. without) · best 6th · Apr 2022 – Sep 2022

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

Rating history

-195-2813820172019202120232025Helm rating, full-size sailingCrew rating, full-size sailing

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

Event history · 118

DateEventBoatClassRoleFinish
24 Oct 20262026 Fall Brawl InvitationalDragonflyJ/105Owner7th / 16
19 Sep 20262026 Hospice Cup XLVDragonflyJ/105Owner6th / 9
12 Sep 20262026 Navy Fall Race to OxfordDragonflyJ/105Owner1st / 4
5 Sep 20262026 Labor Day InvitationalDragonflyJ/105Owner11th / 12
22 Aug 20262026 A2C Lighthouse ChallengeDragonflyJ/105Owner1st / 3
2 Aug 20262026 AYC Two Bridge Fiasco RaceDragonflyPHRF handicapOwner17th / 40
22 Jul 20262026 AYC Wednesday Night - Series 3DragonflyJ/105Skipper18th / 30
18 Jul 20262026 BCYA Race to BaltimoreDragonflyPHRF handicapSkipper5th / 12
13 Jul 20262026 Lido 14 Class ChampionshipsA-TeamLido 14Skipper3rd / 11
10 Jul 20262026 Boomerang RaceDragonflyJ/105Owner4th / 7
20 Jun 20262026 One-Design ClassicDragonflyJ/105Owner10th / 14
13 Jun 20262026 Maryland Cures Cancer RegattaDragonflyJ/105Owner5th / 11
6 Jun 20262026 Ted Osius Memorial Twilight RegattaDragonflyJ/105Owner8th / 8
3 Jun 20262026 AYC Wednesday Night - Series 2DragonflyJ/105Skipper25th / 29
16 May 20262026 SCC EWE Spirit CupDragonflyJ/105Owner7th / 15
8 May 20262026 Fawcett's Friday Night Beer Cans SeriesDragonflyJ/105Captain4th / 8
6 May 20262026 AYC Wednesday Night - Series 1DragonflyJ/105Owner23rd / 27
1 May 20262026 Helly Hansen Sailing World Regatta Series - AnnapolisDragonflyJ/105Owner20th / 23
29 Mar 2026Harry Wood Regatta & District 1 ChampsA-TeamLido 14Skipper3rd / 11
1 Mar 20262025/2026 AYC Frostbite Series 2DragonflyJ/105Skipper4th / 15
7 Feb 2026Frostbite RegattaA-TeamLido 14Skipper2nd / 7
1 Jan 20262026 AYC Hangover BowlDragonflyJ/105Skipper3rd / 8
9 Nov 20252025/2026 AYC Frostbite Series 1DragonflyJ/105Skipper10th / 18
25 Oct 20252025 Fall Brawl & J/105 InvitationalDragonflyJ/105Other11th / 16
18 Oct 20252025 J/105 Chesapeake Bay ChampionshipDragonflyJ/105Skipper20th / 20

Helm rating, Full-size sailing: 133, #28,044.Crew rating, Full-size sailing: 51, #35,524. Compiled from public results; not an official ranking.