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1
Put the potatoes in a large saucepan and add the red wine vinegar, 2 tablespoons of the olive oil, the bay leaf, peppercorns, and salt to taste. Cover with cold water and bring to a boil. Reduce the heat to medium and cook at a low boil 12 to 15 minutes, or until the potatoes are tender enough to be pierced with a skewer. Drain in a colander; do not allow them to cool, or they will break instead of smash.
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2
Put a potato on a clean dishcloth on a work surface, cover with another clean dishcloth, and using the palm of your hand, slowly and gently smash (crush) the potato. Transfer to a tray. Repeat with the remaining potatoes. Spoon the remaining 1/4 cup olive oil over the potatoes. Do not oil the bottoms of the potatoes, or the tapenade will not stick well when it is applied.
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3
Heat a large cast iron skillet over medium-low heat until a drop of water sizzles on the surface. Put the potatoes on the hot surface, oiled side down, and cook until they are crisp on the first side, about 5 minutes: DON'T MOVE THEM! Transfer to a tray, crisp side down.
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4
Slide a wide spatula under a crisped potato. Spread a heaping tablespoon of tapenade on top, and press down lightly to compact the crust. With one quick move, flip the potato over onto the hot surface, tapenade side down, and lower the heat slightly. Repeat with the remaining potatoes, and brown them for about 7 minutes, or until the tapenade is crisp. Carefully remove the potatoes as they are cooked and invert onto a serving platter, tapenade crust facing up. Serve immediately.
