Donald J. Trump the person is literally "winning" at every moment of every day. He lifts not a single atom of his being to do domestic work; being waited on 24/7 for cleaning, laundry, transportation, cooking (always remember that Trump prefers his steaks well done with ketchup), etc. He is surrounded by yes-men so his ego and sense of superiority is never challenged. Further still he quite literally has the power to ruin the lives and careers of people who do challenge him ensuring that his ego is always getting fatter. Because of the position he now holds anyone who matters has to listen to him, has to meet him, has see him, has to be polite to him, etc. There is never a moment where a cameraman, Trumps favorite person, isn't ready to watch and listen indefinitely. He has lead an immoral scandalous life filled with sexual and financial criminality that has only ever rewarded him with more power, money and cabalic connections.
Stripping away the politics and looking just at Trumps pathology, where only he alone matters, how could he be anything but winning right now?