In a crockpot, pour in all of the stewed tomatoes, sugar and oregano. Set on high.
In a large sauce pan, melt the butter and add the sliced celery and chopped onion. Cook until onion is clear and celery is soft. Around 15 minutes.
Remove from heat and then stir in the pesto. When well incorporated, combine this mixture into the crockpot with the tomatoes.
Cook in your crockpot for 6 hours on high. Make sure you walk into your kitchen every once in a while just to smell the amazing aroma it is going to provide!
After six hours, transfer the soup by two cupfuls at a time into a blender and blend until smooth. Put into a separate bowl until all the soup has been blended. Then transfer the blended soup back into the crockpot and add your heavy cream.
Let cook for one more hour and then get ready for this soup to disappear. Never EVER make just one batch. I always double this!