Heat a large deep pot over medium heat; add bacon and cook until barely crisp, about 5 minutes.
Remove bacon to side - discard all but 1 Tbsp of the drippings
Add garlic and cook, stirring, over medium heat, 1 minute.
Add tomatoes and their juice, breaking up tomato pieces with your hands or a wooden spoon.
Add broth, sugar and black pepper; bring to a boil then reduce heat and simmer 15 minutes w/lid ajar
Puree soup in batches in a blender or food processor
Return to pot, stir in cream until incorporated and heat through (2-3minutes)
Remove from heat and stir in vinegar
Garnish with crumbled bacon