Heat a medium size pan over high heat. Saute the garlic with olive oil and toss the heirloom tomatoes until heated through, approximately 5 minutes. Season with salt and pepper. Toss in 1/4 cup of the fresh basil before serving dish.
Peel and dice the potatoes and place in a small bowl. Blanch the potatoes lightly in salted water and rinse in ice water to keep the color.
Mix the cooled, cooked potatoes with the flour, eggs, and roasted garlic. Form mixture into a dough. Roll the dough onto a lightly floured surface, into a snake approximately 1/2-inch thick. Cut into 1/2 inch pieces and using your hands, roll each piece into balls.
Cook the dumplings in boiling water. Cook for approximately 2 minutes. Using a slotted spoon, remove the dumplings and toss with the Heirloom tomato ragu.
To serve, add the remaining torn fresh basil, and serve immediately on a large platter.