Ironically the only 'winning' in Spencer's life is due to his privilege. Specifically being born to rich parents.
The only reason he's not a more prolific cow is because he doesn't have to beg and scrape for a living, so he's able to just disappear quietly into the background for weeks or months at a time in between supporting democratic candidates, destroying right wing movements, going on cocaine fuelled rage benders, getting into relationships with radical leftists, fucking his peers partners, sieg heiling for attention after inviting the media into the room, being serially embarrassed on primetime networks and social media, giving attention whoring and generally backstabby takes on twitter any time something significant happens, and plenty of other stuff.
I mean, other than all the stuff above that the man does in between eating his gourmet burgers (with melted swiss cheese, roasted mushrooms, and caramelised onions), he really isn't a cow at all.