Dice the shallots into fine 1/8-inch pieces and halve the cherry tomatoes lengthwise. Trim the green beans and cut them into 2-inch lengths. Pit and slice the black olives into rings. Drain and rinse the capers to remove excess salt. Fill a large pot with salted water and bring it to a boil, then add the whole potatoes and cook for 15-20 minutes until fork-tender. This timing allows you to prep all your vegetables while the potatoes cook.
When the potatoes are tender, carefully remove them with a slotted spoon and set aside to cool slightly. Keep the potato water at a boil and add the trimmed green beans, cooking for 2-3 minutes until they're tender but still have a slight bite. Immediately transfer the beans to an ice bath or rinse them under cold running water to stop the cooking and preserve their bright color. Drain them well and pat dry.
In one bowl, whisk together the red wine vinegar, 2.5 tablespoons olive oil, salt, pepper, and oregano to create the main vinaigrette. In a separate bowl, combine the diced shallots, halved cherry tomatoes, 1.5 tablespoons olive oil, salt, pepper, oregano, and red pepper flakes—this creates a bright, seasoned base that will absorb flavors and add freshness. I like to let the tomato mixture sit for a few minutes so the flavors start to meld before combining everything.
Once the potatoes have cooled enough to handle, cut them into bite-sized chunks and place them in a large mixing bowl. Pour the vinaigrette from Step 3 over the warm potatoes and gently toss—warm potatoes absorb dressing better than cold ones, which is why I always dress them while they're still slightly warm. Add the cooked green beans from Step 2, the seasoned tomato mixture from Step 3, and the sliced black olives, folding everything together gently to combine without breaking the potatoes.
Heat 2 tablespoons of olive oil in a small skillet over medium-high heat. Once shimmering, add the drained capers and fry for about 1 minute, stirring occasionally, until they begin to crisp and pop slightly. This brief frying brings out their briny flavor and adds textural contrast. Scatter the warm crispy capers over the assembled salad just before serving for maximum flavor and crunch.