History’s Best and Worst Investments
The bets that turned pocket change into fortunes — right next to the ones that vaporized life savings.
Best
- 1
Bitcoin
From about $0.003 to a $69,044 peak — the exact starting price is fuzzy, but the order of magnitude isn’t.
~230,000x
2010 – Nov 2021 ATH
- 2
Amazon (from IPO)
Held since the May 1997 IPO to today.
~2,500x
$10,000 → ~$25M
- 3
Apple (from IPO)
$1,000 invested at the IPO would be worth roughly $2.5M today.
+241,810%
Dec 1980 – Jan 2025
- 4
Nvidia
$1,000 became roughly $12,000 over five years.
+845%
2023–2024, AI boom
Worst
- 1
Bernie Madoff Ponzi scheme
Some claims quote $65B in "phantom" value — the real principal lost was closer to $17–20B.
~$17–20B lost
exposed Dec 2008
- 2
Enron collapse
Stock fell from $90 to 61 cents.
~$63B erased
Jan 2001 – Jan 2002
- 3
Lehman Brothers bankruptcy
Stock lost 93% of its value in its final week alone.
$639B in assets
Sept 2008
- 4
Terra/Luna crypto collapse
LUNA fell from $117 to effectively $0 — a 99.99% loss.
~$40B wiped out
May 2022
Sources
- CoinCodex / Bitbo — Bitcoin historical price data (2010–2021)
- CNBC / Fox Business — Amazon and Apple long-term return coverage (2025)
- DOJ / CNBC — Madoff case reporting (2008–2009)
- NBER working paper — Terra/Luna collapse analysis (2022)
Last updated August 2026
Ad space
See Where You Stand
Cite or Embed This Ranking