Orange County Bancorp (OBT) had the lowest return between 2000 and 2009 by a US stock with a market cap of $250M+, returning -100%.

ASSET	YEARS	% RETURN
Orange County Bancorp (OBT)	2000-2009	-100%
Marvell Technology (MRVL)	2000-2009	-100%
Banco Bradesco SA ADR (BBD)	2000-2009	-100%
America Movil SAB de CV ADR (AMX)	2000-2009	-100%
Fortis (FTS)	2000-2009	-100%
Kronos Worldwide (KRO)	2000-2009	-100%
Molson Coors Beverage (TAP.A)	2000-2009	-100%
PCB Bancorp (PCB)	2000-2009	-99.99%
Millicom International Cellular (TIGO)	2000-2009	-99.99%
Red Cat (RCAT)	2000-2009	-99.92%
Travere Therapeutics (TVTX)	2000-2009	-99.85%
Enersys (ENS)	2000-2009	-99.83%
Gilat Satellite Networks (GILT)	2000-2009	-99.81%
Cantaloupe (CTLP)	2000-2009	-99.27%
LightPath Technologies (LPTH)	2000-2009	-99.08%
TG Therapeutics (TGTX)	2000-2009	-99%
Sify Technologies (SIFY)	2000-2009	-98.98%
Viavi Solutions (VIAV)	2000-2009	-98.88%
Sirius XM (SIRI)	2000-2009	-98.71%
Fennec Pharmaceuticals (FENC)	2000-2009	-98.2%
Sapiens International (SPNS)	2000-2009	-98.11%
Arena (AREN)	2000-2009	-98.1%
Astrana Health (ASTH)	2000-2009	-97.81%
American International (AIG)	2000-2009	-97.76%
Kratos Defense & Security Solutions (KTOS)	2000-2009	-97.71%