Place the tomatoes in a strainer set over a bowl and allow them to drain for about 15 minutes. Transfer the liquid from the bowl into a measuring cup, then fill with water to get 2 ½ cups.
Heat ¼ cup olive oil in a large heavy bottomed pot or dutch oven over medium heat. Add the onion and fennel and sauté until softened and barely starting to turn golden, about 10 minutes. Stir in the fennel seeds and 1 ½ teaspoons salt for about 1 minute more.
Add the arborio rice, stir, and cook for about 1-2 minutes to toast the rice. Add the white wine and stir until fully absorbed.
Add ½ cup of the tomato water and stir. When the rice absorbs all of the liquid, continue adding more tomato water one ½ cup at a time, while stirring, until all the liquid is used up.
Stir in the tomatoes and cook for about 2-3 minutes. They will release some liquid as they start to cook down.
Add the remaining 1 ½ teaspoons of salt and season with black pepper. Give the risotto a taste and adjust the seasoning as needed. While tasting, take note of how done the rice is. When the rice is cooked through but still al dente, it's done.
Remove the risotto from the heat and vigorously stir in the remaining ½ cup of olive oil, then the herbs, reserving some on the side for garnish.
Spoon the risotto into bowls, drizzle with more olive oil and sprinkle with more herbs. Serve immediately.