Wash the potatoes, poke a few holes in them with a fork OR cut the potatoes in half. The more exposed potato flesh, the more pickle juice flavor they will absorb. If any of the potatoes are much larger than the others, cut those ones in half so they cook at a similar rate.
Place the potatoes in the pot, pour the pickle juice over the potatoes, cover the pot with a lid, and bring the potatoes to a boil over high heat.
Once boiling, reduce the heat to medium-low, and simmer for 15 minutes or until the potatoes are tender when poked with a paring knife.
While you’re at the stove, preheat the oven to 425 degrees Fahrenheit.
Remove the potatoes from the heat, dump out the pickle brine, and tip the potatoes onto a rimmed baking sheet. Allow the potatoes to cool for 5-10 minutes. (This will make the potatoes easier to squish).
After 5-10 minutes, drizzle 1 tablespoon of olive oil over the potatoes, season with the salt, and toss to coat.
Use the bottom of a glass or a measuring cup (or anything flat) to lightly squish the potatoes to create nooks and crannies that will crisp up when roasted.
Place the baking tray with the smushed potatoes into the preheated oven and bake for 20-25 minutes or until they are lovely and golden brown with crispy bottoms.
While the potatoes are roasting, finely chop the dill pickle and the fresh dill, and set aside.
When the crispy potatoes are ready, remove them from the oven and toss in a bowl with the remaining olive oil and fresh dill.
Top with chopped pickles and serve hot, warm, or at room temperature.