Usually means: Heel of boot; Missouri region.
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We found 6 dictionaries that define the word bootheel:

General (6 matching dictionaries)
  1. bootheel: Merriam-Webster
  2. Bootheel, bootheel: Wordnik
  3. bootheel: Wiktionary
  4. bootheel: Infoplease Dictionary
  5. bootheel: Dictionary.com
  6. Bootheel (disambiguation), Bootheel: Wikipedia, the Free Encyclopedia

Definitions from Wiktionary (bootheel)

noun:  The heel of a boot.
noun:  An area of land protruding south of the eastern or western end of a southern border.

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