The “biggest” roulette winners are usually measured by a mix of absolute profit and inflation‑adjusted amounts, and many figures are estimates based on reports rather than audited records
Ten biggest roulette winners (commonly cited)
#
Player / Group
Approx. win (original)
Context / notes
1
William Darnborough
≈ 400,000 USD → ≈ 12M today
Early 1900s Monte Carlo streaks and reputed “five in a row” single‑number hits.
2
Richard Jarecki
≈ 1.28M GBP / 10M USD total
1960s–70s, exploited wheel bias in European casinos, record win at San Remo.
3
Joseph Jagger
≈ 65,000 GBP → multi‑million today
1870s engineer who “broke the bank” at Monte Carlo by finding a biased wheel.
4
Billy Walters & partner
3.8M USD
1980s–90s, wheel‑bias play at Atlantic Club Casino, Atlantic City.
5
Gonzalo García‑Pelayo (family)
≈ 5M EUR
1990s, Spanish family team using computer analysis of biased wheels.
6
Charles “Charlie” Wells
≈ 2M francs
1891, twice “broke the bank” at Monte Carlo in legendary streaks.
7
Sir Philip Green
≈ 2–4M GBP / USD
2004, UK retail tycoon won about 2M GBP in one night, then another ≈1–2M later.
8
Pedro Grendene Bartelle
3.5M USD
2017, Brazilian billionaire hit number 32 at Hotel Conrad, Uruguay.
9
Mike Ashley
800k–1.3M GBP
2008, Newcastle United owner won big on a “complete bet” on 17 in London.
10
Ashley Revell
135,300 → 270,600 USD
2004, famously bet his entire net worth on red in Las Vegas and doubled it.
Notes on these records
Exact rankings differ between sources because some include inflation adjustments and lifetime winnings, while others list single‑session hits only.
