Preheat your oven to 375°F (190°C).
Spread the torn pita pieces across a large rimmed baking sheet. Drizzle with 3 tablespoons of olive oil and toss with your hands until well coated.
Bake for 5 to 7 minutes, tossing once halfway through, until the pita edges turn deep golden brown and feel crisp. Set aside to cool completely.
Place the diced tomatoes into a fine-mesh strainer set over a bowl. Allow them to drain for 10 minutes, then discard the liquid.
In a large salad bowl, combine the chopped romaine, drained tomatoes, diced cucumbers, sliced radishes, fresh mint, and flat-leaf parsley.
In a small glass bowl, whisk together the extra virgin olive oil, fresh lemon juice, pomegranate molasses, ground sumac, and kosher salt until smooth and emulsified.
Drizzle the dressing over the vegetables and toss thoroughly using tongs until every leaf is coated.
Add the cooled, crispy pita chips to the bowl just before serving and give the salad one gentle fold so the bread stays crunchy.