Sailor · 2013–2025

Ray Pepi

breakwater yc PHRF handicap J/109 Handicap

Search sailors · About these ratings

Events: 47
Win rate: 0%
Podium rate: 11%
Typically beats: 37%
Best class ranking: #62

Biggest lift: Matt Temares
Longest-running crew: Kevin Costello
Nemesis: David Rosow
Rival: Robert Schwartz
Best day: 18 Jul 2018
Signature result: 2nd of 10

Partnerships · 47 sailors

Kevin Costello · Cleo · J/109 8events 0 wins together · 0 podiums · 0% win rate · 0 of 71 races won Beat 29% of the fleet together(−3 vs. without) · best 6th · Jun 2015 – Aug 2019
Will Pepi · Cleo · J/109 7events 0 wins together · 0 podiums · 0% win rate · 0 of 61 races won Beat 31% of the fleet together(−1 vs. without) · best 9th · Jun 2015 – Aug 2019
Matt Temares · Cleo · J/109 6events 0 wins together · 0 podiums · 0% win rate · 0 of 51 races won Beat 32% of the fleet together(±0 vs. without) · best 6th · Jun 2017 – Aug 2019
Rand Milton · Cleo · J/109 6events 0 wins together · 0 podiums · 0% win rate · 0 of 51 races won Beat 32% of the fleet together(±0 vs. without) · best 6th · Jun 2017 – Aug 2019
Sarah Alford · Cleo · J/109, PHRF handicap 3events 0 wins together · 0 podiums · 3 events · 0 of 21 races won Beat 27% of the fleet together(−4 vs. without) · best 5th · Jun 2019 – Aug 2019
Scott Adler · Cleo · J/109 3events 0 wins together · 0 podiums · 3 events · 0 of 28 races won Beat 30% of the fleet together(−1 vs. without) · best 11th · Jun 2015 – Jun 2017
Lionel Crear · Cleo · J/109 2events 0 wins together · 0 podiums · 2 events · 0 of 15 races won Beat 35% of the fleet together · best 11th · Jul 2016 – Jun 2018
Lisa Fischoff · Cleo · J/109 2events 0 wins together · 0 podiums · 2 events · 0 of 16 races won Beat 26% of the fleet together · best 11th · Jun 2018 – Oct 2018
James Fales · Cleo · J/109 2events 0 wins together · 0 podiums · 2 events · 0 of 20 races won Beat 24% of the fleet together · best 6th · Jun 2019 – Aug 2019
Dave Coughlin · Cleo · J/109 2events 0 wins together · 0 podiums · 2 events · 0 of 20 races won Beat 19% of the fleet together · best 13th · Jun 2015 – Jul 2016

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

Rating history

Event history · 47

Date	Event	Boat	Class	Role	Finish
27 Sep 2025	Whitebread 32	Odyssey	PHRF handicap	Skipper	10th / 32
28 Sep 2024	Whitebread 31	Odyssey	PHRF handicap	Skipper	15th / 31
10 Aug 2024	Antigua and Barbuda Hamptons Challenge Regatta	Odyssey	Handicap	Skipper	5th / 6
5 Jun 2024	2024 The Breakwater Yacht Club - Summer Series I	Odyssey	PHRF handicap	Skipper	5th / 7
6 Sep 2023	2023 The Breakwater Yacht Club - Fall Series	Cleo	PHRF handicap	Other	5th / 5
26 Aug 2023	54th Lawrence I. Clarke Memorial 'Round Gardiner's Island Race	Cleo	PHRF handicap	Other	3rd / 4
23 Aug 2023	2023 The Breakwater Yacht Club - Summer Series III	Cleo	PHRF handicap	Skipper	4th / 5
19 Jul 2023	2023 The Breakwater Yacht Club - Summer Series II	Cleo	PHRF handicap	Skipper	5th / 5
15 Jul 2023	41st Annual Sag Harbor Cup	Cleo	J/109	Other	4th / 7
7 Jun 2023	2023 The Breakwater Yacht Club - Summer Series I	Cleo	PHRF handicap	Other	5th / 5
24 May 2023	2023 May Cup	Cleo	PHRF handicap	Other	5th / 6
24 Sep 2022	2022 Maycroft Cup	Cleo	PHRF handicap	Other	3rd / 6
10 Sep 2022	40th Annual Sag Harbor Cup Benefit Regatta	Cleo	PHRF handicap	Other	7th / 8
7 Sep 2022	2022 The Breakwater Yacht Club - Fall Series	Cleo	PHRF handicap	Other	5th / 7
27 Aug 2022	53rd Lawrence I. Clarke Memorial 'Round Gardiner's Island Race	Cleo	PHRF handicap	Other	4th / 5
13 Aug 2022	Antigua and Barbuda Hamptons Challenge Regatta	CLEO	PHRF handicap	Skipper	2nd / 10
10 Aug 2022	2022 The Breakwater Yacht Club - Summer Series II	Cleo	PHRF handicap	Skipper	7th / 7
1 Jun 2022	2022 The Breakwater Yacht Club - Summer Series I	Cleo	PHRF handicap	Other	5th / 7
4 May 2022	2022 May Cup	Cleo	PHRF handicap	Other	6th / 6
28 Sep 2019	2019 American Yacht Club Fall Regatta	Cleo	J/109	Other	9th / 13
21 Aug 2019	2019 J 109 North American Championship	Cleo	J/109	Skipper	9th / 11
3 Jul 2019	2019 The OZ Trophy	Cleo	PHRF handicap	Other	5th / 7
24 Jun 2019	2019 Storm Trysail Club Block Island Race Week	Cleo	J/109	Helm	6th / 8
5 Jun 2019	2019 The Breakwater Yacht Club - Summer Series - With Penalties	Cleo	PHRF handicap	Other	8th / 8
1 Jun 2019	2019 Cedar Point One Design Regatta - Keelboat	Cleo	J/109	Helm	10th / 16

Ratings

Class	Rating	Rank	Impact
All classes Helm	142	#25987 band 20126–33062	—
J/109 Helm	61 provisional	#62 band 42–76	−3.3

1 more class, not yet ranked

All classes · Crew · 1 race, 1 event · rating 1

Rank among sailors with a substantial record, all time. In brackets, the ranks this rating cannot be told apart from. Impact is the points of fleet beaten that this sailor adds.

Helm and crew

As helm	46 events	0 wins	beats 31%
As crew	1 events	0 wins	beats 33%

How they race

Closer	−4 pts	last race of an event vs. the rest
Comeback	−4 pts	the race after a bottom-half finish
Consistency	55%	100% = the same result every event
Big fleets	50%	of the fleet beaten
Small fleets	28%	of the fleet beaten

Head to head

Helm	Races	W–L
Carl Olsson	126	30–96
David Rosow	98	5–93
Robert Schwartz	98	50–48
Bengt Johansson	96	14–82
Jr. John Greifzu	95	38–57
William Rogers	93	28–64
Jonathan Rechtschaffer	90	11–79
Cory Eaves	88	71–17
Bill Kneller	88	40–48
Bill Sweetser	81	9–72
Ted Herlihy	75	16–59
Bud Rogers	74	9–65

Most-beaten opponent: Cory Eaves (71–17).

Seasons

Year	Events	Beat
2025	1	71%
2024	3	36%
2023	7	18%
2022	8	32%
2019	6	26%
2018	7	39%
2017	8	38%
2016	4	41%
2015	1	13%
2014	1	8%
2013	1	0%

Boats

Cleo · PHRF handicap, J/109 · 43 events · 2013–2023
Odyssey · PHRF handicap, Handicap · 4 events · 2024–2025

Where they race

Sag Harbor, NY, USA · 20 events
Rye, NY, USA · 5 events
New Suffolk, NY · 4 events
Block Island, RI, USA · 3 events
Larchmont, NY, USA · 3 events
Amagansett, NY, USA · 2 events

Is this you?

Claim it to merge duplicates and remove results that aren’t yours. Changes apply at the nightly rebuild.

Helm rating across all classes: 142, #25,987.Crew rating across all classes: 1. Compiled from public results; not an official ranking.