The May 27, 1896 St. Louis/East St. Louis tornado has been shown to be the costliest tornado on record. A “best guess” tornado damage path has been obtained for this historic event through the synthesis of literature and photographic analysis and some simple assumptions based on other historic tornado paths. This hazard data has been used as input into the proprietary catastrophe modeling technologies developed by Risk Management Solutions, Inc. to estimate the total damage and insured loss if this scenario were to occur with year 2000’s building, content, and time element exposures. The results of the scenario model will be contrasted with the $2.2-2.9 billion loss estimate obtained through wealth adjustment of historic losses.