~$250,000
Personal loss sustained by Henry A. DeLand when he honored his freeze-loss guarantee to settlers who had planted orange groves on his word.
Source: Wikipedia [S01]
Quick answer: The Great Freeze of 1894–95 was a back-to-back Florida freeze that collapsed the state's citrus industry. DeLand founder Henry A. DeLand had personally guaranteed settlers against freeze losses; honoring that promise cost him nearly $250,000 and ultimately bankrupted him.
Two hard freezes in December 1894 and February 1895 destroyed the young citrus groves across Central Florida. The second freeze was worse than the first because the trees had begun to re-sprout, and the cold killed the trunks as well as the fruit.
Henry A. DeLand had promised he would cover anyone who moved to the area and planted oranges against loss of their crop to a freeze. When the freeze came, he honored the promise and lost nearly $250,000 [S01, S02].
Personal loss sustained by Henry A. DeLand when he honored his freeze-loss guarantee to settlers who had planted orange groves on his word.
Source: Wikipedia [S01]By 1896, DeLand had sold all his property in Florida and in Fairport, New York. He died penniless on March 13, 1908 [S01].
Read Henry A. DeLand's biographyJohn B. Stetson's philanthropy was one of the key reasons the university — and by extension the town's cultural infrastructure — survived the economic collapse [S19, S20].