Mine isn't all that 'shameful' depending on who you are but it was very on the fence for me.
I'm a soloer by nature but on fridays my one friend joins in for some high seas shenanigans. We were coasting down for the night which means hes going to do something to drag me back in for 2 more hours...So I'm sitting on an outpost around midnight hoping we might actually call it a night on time for once when I foolishly muse over the fact that we managed a little bit of everything that night but no pvp. So he takes the ship out without me....
Speed up this part but we take turns having our games freeze(so luckily our ship was in tact with one of us being online at all times) and by the time we are regrouped I am back on the ship from relogging and he has drifted us towards an active skull fort...and it just ends...with a single sloop at it.
Now whether or not to attack said sloop depends on who you are but as a hardcore soloer and someone with little interest in skull forts I would normally never do this but somehow he has convinced me to go for it...
So one attempted anchor drop on us and one successful anchor drop later(the guy had mouse and keyboard speed so he got the better of us) we respawn, kill him, and make for the outpost that they stopped out...really it's their own fault they should have kept going while we were out not stop at the outpost right next to where they anchor dropped us...
As we approach the anchor dropper goes back into the water...not sure why we havent stopped, and his partner tries to pull out fast but we come up alongside him, open fire killing him...but the dang ship coast turns around Dagger Tooth and slames and wedges itself between the beach and the rocks perfectly setting itself to never sink...seeing this I sneak ashore(using a storm that just hit as cover...I'm talking the outpost was the center of the storm type rain). My friend distracts them with constant cannon fire I slip aboard and start throwing stuff on the beach and hiding it in the bushes and behind rocks. We dance off and on with the crew, I get about half of there stuff hidden before they find me. Eventually they get their ship unwedged and sink my friend cause I'm the sailor in our group. I let them do it so I can sell off some of the more expensive loot and that walk from the backside of the island is a pain.
My friend abandons ship and we clash on the island a few more times before they finally kill us off and we respawn at our ship a distance away. We make are way back and see the sloop speeding from the outpost and avoiding our return. We find the rest of our loot in the bushes, they never found it, and cash in. I have heard that skull fort payouts aren't necessarily worth the time investment to solo...well they really aren't worth the time investment to steal either...
While I admit to it being a rather epic story with combat, thievery, and hidden loot and should I take the time to flush it out with proper pirate narration would be an interesting read...part of me feels dirty. It may work for some people...but it wasn't the type of pirate I wanted to be...