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I think this would require a WW2 era POD. At the minimum the Dominion of Canada should add the following territories in the post-war period:
- Newfoundland
- St. Pierre & Miquelon
- Bermuda
- Antigua and Barbuda
- The Bahamas
- Barbados
- Dominica
- Grenada
- Jamaica
- Saint Kitts and Nevis
- Saint Lucia
- Saint Vincent and the Grenadines
- Trinidad and Tobago
- British Honduras
- British Guyana
- Anguilla
- British Virgin Islands
- Cayman Islands
- Montserrat
- Turks and Caicos
- Dominica
- French Guiana
- Guadeloupe
- Martinique
- Saint-Barthélemy
- Saint Lucia
- Saint Martin
Bonus-points if you can include Suriname and the Netherlands Antilles.