1986 – Monroe County Commissioners wanted to get rid of the Boot Key Bridge, which cost taxpayers thousands of dollars a year to maintain and operate, just so vehicles could access a radio station and trap factory on the otherwise empty island. The bridge tender testified that the bridge had to be opened for boat traffic 1429 times over the previous two months.

1975 – After refusing to pay a new $11 per cubic yard disposal fee, the City of Key Colony Beach was barred from using the Monroe County dump at Boot Key. Key Colony had a policy of not charging for trash pickup, and the mayor vowed not to break it.

2008 – The dilapidated, Depression-era bandstand at Bayview Park in Key West was torn down. The bandstand had once been a community hub and the site of concerts, political rallies, and high school graduations.