Place your pan on the stove and heat to medium. Add beef and season heavily with salt and pepper. Cook and crumble until browned, with no pink remaining.
Turn off the heat and drain excess fat. Transfer beef to your large mixing bowl. Clean the pan you used to cook the beef – we’ll use it again when assembling and toasting the quesadillas.
To the same mixing bowl, add ketchup, mustard, mayonnaise, onion, pickle, garlic powder, and onion powder. Stir until combined. Taste, and adjust condiments and seasonings as desired. Your mixture should be moist but not wet to ensure crispy quesadillas.
Return your clean pan to medium heat. If desired, coat the pan with a thin layer of cooking spray – I prefer to toast my quesadillas dry, but it depends on your pan!
Add a tortilla to the pan. On one half, add ¼ cup of cheddar. Spread ¼ of the meat mixture directly on top. Finish with another ¼ cup of cheddar. Fold the tortilla in half and press down firmly. Cook for 2-3 minutes on each side, or until both are golden brown and crisp. Remove from the pan and transfer to a cutting board. Repeat for all quesadillas.
Slice each quesadilla into triangles. Enjoy immediately with condiments of choice!