Mix the burger sauce. In a small bowl, combine mayonnaise, sugar-free ketchup, mustard, and pickle juice. Set aside.
This will be your drizzle at the end.
Heat the skillet. Place a large cast-iron or heavy skillet over medium-high heat. Add oil and let it shimmer.
Caramelize the onions. Add sliced onions with a pinch of salt. Cook 5–7 minutes, stirring occasionally, until soft and golden.
Push to the edges of the pan.
Season the beef. In a bowl, gently combine ground beef with salt, pepper, smoked paprika, minced garlic, and Worcestershire. Do not overmix; you want it loose.
Form loose balls. Divide the beef into 6–8 loose mounds (about 3 ounces each). Keep them rough; this helps create those craggy, crispy edges.
Smash and sear. Increase heat to high.
Place 3–4 mounds in the center of the skillet. Using a spatula or burger press, smash each into a thin patty (about 1/4 inch). Don’t move them for 2–3 minutes until deeply browned.
Flip and cheese. Flip each patty, add a slice of American or cheddar on top, and cook 1–2 more minutes until the cheese melts.
Transfer to a plate and repeat with remaining patties.
Butter finish. Reduce heat to medium. Add butter to the skillet and let it melt into the oniony, beefy drippings. Scrape up browned bits for extra flavor.
Return patties and add shredded cheese. Nestle all patties back into the skillet with the onions.
Sprinkle shredded cheddar or Monterey Jack over everything. Cover with a lid for 1–2 minutes to melt.
Add fresh toppings. Remove from heat. Scatter dill pickles, diced tomato (if using), and shredded lettuce over the skillet.
Drizzle with the burger sauce.
Serve hot. Spoon into bowls or serve family-style. Add hot sauce or red pepper flakes if you like heat.