And often the "winner" is the one who has the best lawyer. So, who is likely to have the better lawyer. The DJ who mixes on weekends or Sony Music? This is more a flaw in the court system I guess, but it doesn't make it hurt any less.
I am reminded by the George Hotz versus Sony entertainment. He "jailbroke" the PS3 to run homebrew (and install other OS's, a functionality that Sony initially supported) and was taken to court. Long story short, he was forced to agree not to mess with anything Sony for the rest of his life. - - - this is a slightly different example, but falls roughly into the same category.
Apple also went to court; their goal was to stop Jailbreaking the iPhone. By the way, Jailbreaking the iPad is still up in the air as far as the legal rulings are concerned. In no way, did the Copyright Office say it applied to all iDevices; the iPad did not exist at the time.
As for winners have better lawyers than losers, I might cite a few quick examples of large uber-corporations that lost in court when they went up against a rather nice lady who was using their legally protected images on products she sold on eBay, and she had no legal experience and no licensing agreements. Ruled legal by the courts.
In each case, it was all about copyright violations and the rights that these corporations asserted that resulted in cases tossed out of court because the lawyers were asserting "rights" they had no (legal) right to assert.
So the little guy can often defeat the giants among us, when the court is reasonable and the facts support you.
Consider . . . this woman created children's clothing featuring images and other IP owned by Major League Baseball, NASCAR, and many of the images of Walt Disney's beloved characters, like Donald and Mickey.
Her cased was based on existing law that says what you can do and cannot do. In this case, it was fabrics licensed to the fabric manufacturer. She made children's clothes and Disney (and others) disagreed and cited IP and copyright violations.
The court disagreed and she won. Several times, in fact.
In my opinion, I think these "David V. Goliath" cases are lost because either you are not prepared, you assume too much, you have an incompetent/inexperienced lawyer, or the law is not on your side. You assume too much and to casual observers, you are seen as the victim; the large corporations are viewed as greedy and heartless.