Cut tomatoes in large pieces and place in pot with basil, pickle, hot sauce, Colonel Pabst Worcestershire Sauce, oregano, salt and pepper in a soup pot. Bring to medium-low heat and simmer for 10-15 minutes or until tomatoes cook down and become tender.
When tomatoes take on a soupy texture, blend mixture with immersion blender in a food processor until smooth. Place in refrigerator until chilled before using.
To make Bloody Mary: Combine vodka and Homemade Bloody Mary Mix in a glass with ice; stir to combine. Garnish with desired condiments and serve.