First, add the potatoes to a large pot filled with water and about a tablespoon of salt. Bring to a boil and cook until the potatoes are fork tender - about 15 minutes. Once they're done, drain the water and allow the potatoes to cool for about 10 minutes.
Preheat the oven to 450℉. Place the potatoes on a baking sheet. I lined mine with parchment paper. Now it's time to smash using a glass jar, heavy coffee cup or something solid with a flat bottom. Smash them so they're flat on both sides, but not too thin or they'll fall apart easily.
In a small bowl, mix together the oil, oregano and garlic. Use a basting brush to coat both sides of the potatoes with the oil mixture. Season with lots of salt and pepper. Place potatoes in the oven and cook for about 45-50 minutes - flipping halfway through.
While the potatoes bake, make the aioli. If that's not your thing feel free to use another dip. Serve the potatoes on a plater with the aioli dip and garnish with herbs like rosemary or parsley.
Aioli
Add all the ingredients to a bowl and whip together. Store leftovers in the fridge.
Notes
Small potatoes work best for this so if you're potatoes are on the bigger side, after you boil them and they've cooled cut them in half. Place cut side down to smash