Obviously, this depends on context. If you’re being placed tomorrow, I’d rather be the captain of a losing team because as captain I can make them into winners. If we’re talking about outcomes i.e. I was placed a year ago, would I’d rather be the captain of a losing team, or a partipant in a winning team it’s hard to see how being a loser is helpful unless it’s like a “I’d rather lose as a Yankee than win as whatever team you are” sort of situation