Place 10 ounces (300g) of the tomatoes in a shallow medium ceramic or glass dish. Sprinkle with salt and let them sit for 15 minutes—the salt will draw out some of their water and concentrate their sweetness. (No need to drain off any water the tomatoes release since you’ll use it to mingle with the vinaigrette.)

In a medium bowl, combine the remaining 2 ounces (60g) tomatoes, the garlic, olive brine, vinegar, and orange zest. Using an immersion blender, blitz until mostly smooth—a little texture is fine. Add the olives, olive oil, and vinaigrette to the dish. Squeeze the orange half over the top, then season with a pinch more salt. Stir gently, then set aside a few minutes to let the tomatoes soak up the flavors. Transfer the tomatoes to a serving dish, leaving the vinaigrette behind in the bowl.

Spoon as much of the vinaigrette over the top of the salad as you like, depending on your preference for acidity. Sprinkle with fennel pollen and garnish with basil and fennel fronds. Serve any remaining vinaigrette on the side with crusty bread for tearing and swiping.