It seems like everyone has an opinion on this, or an opinion of the people involved. Putting that all aside, the security camera video evidence is crystal clear.
https://youtu.be/KaQwdSekfQg
At the 1:35 mark you can see the O'Leary's boat appear, with its lights on. At 1:53, it hits the other boat. At 2:10, the other boat begins turning on its lights.
Regardless of who has money and who doesn't, the one thing that cannot be disputed is that the boat Mrs O'Leary hit did not have its lights on. The court got it right, fault lies with the operator of the second boat.
Everything else is just window dressing.