Place a medium skillet set over medium heat and cook the diced bacon until crisp. Remove the bacon from the pan with a slotted spoon and set aside.
Meanwhile, remove the corn kernels from the cob by placing a cob on its end on a clean kitchen towel. Using a sharp knife, run down the side of the cob to remove the kernels. Continue with the other two cobs of corn then add the kernels along with the jalapeno, to taste, to the bacon fat and cook until lightly golden brown, about two minutes.
Stir in the green onions and oregano, season with salt and pepper, and add in the cream cheese and milk. Turn the heat down to medium-low and, stirring constantly, allow everything to melt together. When creamy, stir in 3/4 cup of the grated pepper jack cheese and the cooked bacon and adjust the seasoning to taste.
Transfer the mixture into an oven-safe dish and scatter the remaining 1/4 cup of pepper jack cheese over top of the dip and place under the broiler for three or four minutes or until golden brown.
Serve hot with corn tortilla chips or sliced baguette.