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Heat oven to 425°F. Place tots on rimmed baking sheet and bake until browned and crispy, 25 to 30 minutes.
In small bowl, combine half of onion with 2 tablespoons pickle brine. Let sit, tossing occasionally, until ready to use.
Meanwhile, heat oil in large cast-iron skillet on medium. Add remaining onion and cook, stirring occasionally, until tender and golden, 6 to 7 minutes. Add beef and steak seasoning and cook, breaking up meat, until no longer pink, 5 to 6 minutes.
Add tomato paste and cook, stirring continuously, until caramelized and darkened in color, 2 to 3 minutes. Sprinkle with flour and cook, stirring, 1 minute. Gradually add bouillon mixture and simmer, stirring occasionally, until slightly thickened, 3 to 5 minutes; remove from heat.
Sprinkle with 1 cup cheese and top with tots, then remaining ½ cup cheese. Bake until cheese is melted and mixture is bubbling, 5 to 6 minutes.
Meanwhile, in small bowl, whisk together mayonnaise, ketchup, mustard, and remaining tablespoon pickle brine.
Drain pickled onions, then scatter over tots along with tomatoes and pickles. Serve with special sauce on the side.