Bring a large pot of water to a boil. Score the tops of the tomatoes. Add the tomatoes to the boiling water. Allow to boil for 2 minutes. Once the peel readily separates itself from the tomato, place the tomatoes on a plate to cool enough for easily handling.
In a stock pot or Dutch oven over medium heat, heat the oil until shimmery. Add the onions and caramelize until the edges are golden brown.
Add the garlic, Italian seasoning, and oregano. Cook and stir until fragrant.
Pour in the wine and deglaze all the brown bits at the bottom of the pot. Cook until about half of the wine is reduced.
Add the tomatoes and give it a large stir. Once the tomatoes are soft enough to easily press, press them down with the back of a wooden spoon or spatula.
Add the bay leaf and stir. Reduce the heat to a simmer, cover the pot, and allow to simmer for about 15 minutes. Add salt, pepper, and/or sugar to taste.
Remove the bay leaf and serve over cooked pasta.
Notes
*I used Roma tomatoes ** I used Cabernet, but you can also use Merlot or Chianti