Dice bacon and cook over medium heat until crisp. Remove from the pot and discard any burt bits at the bottom.
Keep about 1/4 cup of the rendered bacon fat in the pot.
Add butter to the bacon fat and allow to melt.
Turn heat down to just under medium. Add diced onions and carrots and cook 5 minutes.
Add smashed garlic cloves, stir and cook for 5 minutes.
Add tomato paste, stir and cook for 1 minute. Add canned tomatoes, including all the juice from the cans, chicken stock, Better than Boullion chicken base and a pinch of salt.
Simmer for 30 minutes with the lid off.
Add everything in the pot to a large blender or use an immersion blender to blend until smooth. Wait for the soup to cool down for 5 minutes before blending.
Add the soup back to the pot along with the sugar, salt, pepper, dried basil, dried oregano, red pepper flakes, and half & half. Stir and simmer for at least 1 hour.
If time allows, let the soup simmer, covered on low for hours. It gets better with time.
Stir and serve warm.