Sailor · 2009–2025

Jeff Olshesky

chicago yacht club ORC handicap Farr 40 420

Search sailors · About these ratings

Events: 16
Win rate: 19%
Podium rate: 69%
Typically beats: 52%
Best class ranking: #403
Longest win streak: 4

Most successful partnership: Tim Corkell
Best trio: Pat Considine & Tim Corkell
Biggest lift: Pat Considine
Longest-running crew: Anne Branson
Nemesis: Helmut Jahn
Rival: Jerry O'Neill
Best day: 7 Jun 2013
Signature result: 3rd of 30

Partnerships · 53 sailors

Most successful partnership: Tim Corkell — 2 wins · 5 podiums in 5 events together · 40% win rate

Anne Branson · Eagles Wings, Norboy · Farr 40, ORC handicap 12events 2 wins together · 9 podiums · 17% win rate · 14 of 85 races won Beat 54% of the fleet together(−9 vs. without) · best 1st · Sep 2012 – Aug 2025
Melissa Grim · Eagles Wings, Norboy · Farr 40, ORC handicap, T-10 11events 2 wins together · 9 podiums · 18% win rate · 13 of 77 races won Beat 62% of the fleet together(+18 vs. without) · best 1st · Sep 2012 – Aug 2025
Brenden Jacobs · Eagles Wings · ORC handicap 8events 2 wins together · 8 podiums · 25% win rate · 14 of 57 races won Beat 74% of the fleet together(+35 vs. without) · best 1st · Jun 2021 – Aug 2025
John Gottwald · Eagles Wings · ORC handicap 8events 2 wins together · 8 podiums · 25% win rate · 14 of 57 races won Beat 74% of the fleet together(+35 vs. without) · best 1st · Jun 2021 – Aug 2025
Pat Considine · Eagles Wings · ORC handicap 7events 2 wins together · 7 podiums · 29% win rate · 14 of 50 races won Beat 80% of the fleet together(+41 vs. without) · best 1st · Jun 2021 – Aug 2025
Leif Sigmond · Norboy · Farr 40, T-10 5events 0 wins together · 2 podiums · 0% win rate · 1 of 35 races won Beat 30% of the fleet together(−38 vs. without) · best 3rd · Sep 2012 – Sep 2017
Marcus Thymian · Norboy · Farr 40, T-10 5events 0 wins together · 2 podiums · 0% win rate · 1 of 35 races won Beat 30% of the fleet together(−38 vs. without) · best 3rd · Sep 2012 – Sep 2017
Blair Ross · Norboy · Farr 40, T-10 5events 0 wins together · 2 podiums · 0% win rate · 1 of 35 races won Beat 30% of the fleet together(−38 vs. without) · best 3rd · Sep 2012 – Sep 2017
Brian Moy · Eagles Wings · ORC handicap 5events 1 wins together · 5 podiums · 20% win rate · 7 of 35 races won Beat 71% of the fleet together(+22 vs. without) · best 1st · Jun 2021 – Aug 2025
Tim Corkell · Eagles Wings · ORC handicap 5events 2 wins together · 5 podiums · 40% win rate · 11 of 34 races won Beat 75% of the fleet together(+27 vs. without) · best 1st · Jun 2021 – Jun 2024

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

Rating history

Event history · 16

Date	Event	Boat	Class	Role	Finish
8 Aug 2025	2025 CYC Verve Cup Offshore	Eagles Wings	ORC handicap	Crew	2nd / 4
6 Jun 2025	2025 Helly Hansen Sailing World Regatta Series - Chicago	Eagles Wings	ORC handicap	Mast	2nd / 5
7 Jun 2024	2024 Helly Hansen Sailing World Regatta Series - Chicago	Eagles Wings	ORC handicap	Mast	2nd / 6
11 Aug 2023	2023 Verve Cup Offshore Regatta	Eagles Wings	ORC handicap	Mast	2nd / 5
9 Jun 2023	2023 Helly Hansen Sailing World Regatta Series - Chicago	Eagles Wings	ORC handicap	Mast	3rd / 6
19 Aug 2022	2022 Verve Cup Offshore Regatta	Eagles Wings	ORC handicap	Mast	3rd / 4
10 Jun 2022	2022 Helly Hansen Sailing World Regatta Series - Chicago	Eagles Wings	ORC handicap	Mast	1st / 4
11 Jun 2021	2021 Helly Hansen NOOD Regatta Chicago	Eagles Wings	ORC handicap	Mast	1st / 6
28 Sep 2017	2017 Farr 40 North American Championships	Norboy	Farr 40	Other	5th / 8
6 Oct 2013	2013 Fall Frostbite Series	Ols	420	Skipper	14th / 24
7 Jun 2013	2013 Sperry Top-Sider Chicago NOOD Regatta	Norboy	T-10	Bow	3rd / 30
18 Sep 2012	2012 Rolex Farr 40 World Championship	Norboy	Farr 40	Other	20th / 20
14 Sep 2012	2012 Rolex Farr 40 Pre-Worlds - USA Circuit Event 5	Norboy	Farr 40	Other	17th / 20
8 Sep 2012	2012 Sheldon Clark Regatta	Norboy	Farr 40	Other	3rd / 3
13 Aug 2009	2009 Verve Cup Offshore Regatta	Raven	PHRF handicap	Other	1st / 10
13 Jun 2009	2009 Columbia Yacht Club COLORS Regatta	Raven	ORC handicap	Other	7th / 8

Ratings

Class	Rating	Rank	Impact
All classes Crew	324 provisional	#6426 band 4137–9829	—
Farr 40 Crew	-207 provisional	#403 band 350–425	—

3 more classes, not yet ranked

420 · Helm · 12 races, 1 event · rating -16
All classes · Helm · 12 races, 1 event · rating -29
T-10 · Crew · 7 races, 1 event · rating 81

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	1 events	0 wins	beats 44%
As crew	15 events	3 wins	beats 57%

Positions: Mast (7) · Bow (1)

How they race

Closer	−10 pts	last race of an event vs. the rest
Comeback	−18 pts	the race after a bottom-half finish
Consistency	31%	100% = the same result every event
Small fleets	62%	of the fleet beaten

Head to head

Helm	Races	W–L
Philip Dowd	72	28–44
Jerry O'Neill	51	25–26
David Ward	37	37–0
Christopher Whitford	24	5–19
Stuart Townsend	21	5–16
John Gottwald	18	10–8
Brian Jackman	18	5–13
Helmut Jahn	18	0–18
Lloyd Karzen	15	11–4
Eric Mergenthaler	14	4–10
Alex Roepers	14	3–11
Wolfgang Schaefer	14	3–11

Most-beaten opponent: David Ward (37–0).

Seasons

Year	Events	Wins	Beat
2025	2	0	71%
2024	1	0	80%
2023	2	0	68%
2022	2	1	67%
2021	1	1	100%
2017	1	0	43%
2013	2	0	68%
2012	3	0	5%
2009	2	1	57%

Boats

Eagles Wings · ORC handicap · 8 events · 2021–2025
Norboy · Farr 40, T-10 · 5 events · 2012–2017
Raven · PHRF handicap, ORC handicap · 2 events · 2009
Ols · 420 · 1 events · 2013

Where they race

Chicago, IL, USA · 12 events
Chicago, IL · 2 events
Chicago, Illinois, USA · 1 events
Unknown · 1 events

Is this you?

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

Crew rating across all classes: 324, #6,426.Helm rating across all classes: -29. Compiled from public results; not an official ranking.