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Sailor · 2016–2025

Benson Chiles

ahsep HandicapOptimistORC handicap

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Events
9

55 races · 3 race wins

Win rate
11%

11% win rate · 1 of 9

Podium rate
44%

4 top-three finishes

Typically beats
62%

of boats faced (range 55%–69%, 140 boats)

Longest win streak
3

race wins in a row

Nemesis
Colin Guerrera

9–28 head to head in 37 races

Rival
Esteban Pedroza

16–19 in 35 races

Best day
22 Jul 2017

1-1-1 · BRAVEHEART

Signature result
1st of 7

BRAVEHEART · Handicap · 22 Jul 2017

Partnerships · 7 sailors

  • Taylor Niles · ASSARAIN IV · ORC handicap 1events 0 wins together · 1 podiums · 1 events · 0 of 1 race won Beat 82% of the fleet together · best 3rd · Aug 2025 – Aug 2025
  • Michael Cassidy · ASSARAIN IV · ORC handicap 1events 0 wins together · 1 podiums · 1 events · 0 of 1 race won Beat 82% of the fleet together · best 3rd · Aug 2025 – Aug 2025
  • Mike Neubelt · ASSARAIN IV · ORC handicap 1events 0 wins together · 1 podiums · 1 events · 0 of 1 race won Beat 82% of the fleet together · best 3rd · Aug 2025 – Aug 2025
  • Steve Brownlie · ASSARAIN IV · ORC handicap 1events 0 wins together · 1 podiums · 1 events · 0 of 1 race won Beat 82% of the fleet together · best 3rd · Aug 2025 – Aug 2025
  • Derick Pollack · ASSARAIN IV · ORC handicap 1events 0 wins together · 1 podiums · 1 events · 0 of 1 race won Beat 82% of the fleet together · best 3rd · Aug 2025 – Aug 2025
  • Rick Hough · ASSARAIN IV · ORC handicap 1events 0 wins together · 1 podiums · 1 events · 0 of 1 race won Beat 82% of the fleet together · best 3rd · Aug 2025 – Aug 2025
  • Brian Dellett · ASSARAIN IV · ORC handicap 1events 0 wins together · 1 podiums · 1 events · 0 of 1 race won Beat 82% of the fleet together · best 3rd · Aug 2025 – Aug 2025

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

Rating history

058116201720182019Helm rating, full-size sailing

Event history · 9

DateEventBoatClassRoleFinish
29 Aug 20252025 Vineyard RaceASSARAIN IVORC handicapCrew3rd / 12
18 Oct 20192019 Fall Laser RegattaBenson ChilesILCA 7 (Laser)Skipper11th / 14
18 Aug 2018Sandy Hook Hobie Points RegattaTBDHobie WaveSkipper3rd / 7
6 Aug 2018Junior Sweeps 20185046420Skipper3rd / 15
28 Jul 2018BRAVEHEART007HandicapSkipper5th / 6
7 Aug 2017Junior Sweeps 2017007OptimistSkipper11th / 37
22 Jul 2017BRAVEHEART007HandicapSkipper1st / 7
1 Aug 2016Junior Sweeps 201612169OptimistSkipper18th / 41
16 Jul 2016Braveheart11645HandicapSkipper7th / 10

Helm rating, Full-size sailing: 26, #50,872.Crew rating, Full-size sailing: 22. Compiled from public results; not an official ranking.