Actually, here's a real one for me.
It was the point where I decided to leave Chaos. Don't get me wrong, everything that's developed from there has gone through its own journey which I'm glad for, but it was heartbreaking for me to leave the clan and the organization that we worked hard to put together.
During the Chaos decline, action was almost non-existent and I we were plagued with inactivity, festering and brewing in our own frustration and non-success by our standards. Our glory days long behind us (not that it mattered), we were excited to get into the fight, and do what we do best ("here come those Chaos bundle of stickss to steamroll the server for 2 hours").
Strategus had left us at each others' throats, confused, angry and unsure where to direct our chagrin. Upper management were having an all out battle royale on the forums, which spilled into the public section of our forums. The once mighty battle cult of Stratia's best had fallen into disarray. Canary (coined "the Fuhrer" by our own Weebo) had taken to an iron hand that (in my opinion) needed to be used for the restructure of the faction.
The old Chaos by now had deteriorated into a faction that accepted any joe dirt off the street with an amicable personality, with no clauses to maintain the high standards which were a prominent strategy - called the "applicant pants." It was a majority rule, and people were overtaken by the group think did not oppose new members out of either disregard or conflict avoidance. The result was the same.
Stagnation, the dilution of combat skill level. The overall reduction across the board on teamwork (Cohesion and Synergy™), and the descent into trolly attitude among bored members who were simply looking for fresh ways to play the game they enjoyed with good company. The Chaos of old had reached a low point, where even its then-highest ranked members lost faith in the future of the Clan. I lost faith in Chaos.
In a way, our exodus from Chaos was beneficial to both our own peace of mind as well as their player base. Most of those who chose to leave Chaos without pledging their allegiance to us decided to make their own short termed clan with no future (as I'm sure they knew during inception). Those who followed us marched away from our own brothers, our home. Those who stayed watched us leave, sad (I'm sure) but hopeful at a chance of a cleaner future.
My decision to leave the clan that I helped found, the decision to leave the leader I helped instate, the decision to leave he whom I had once pledged to support, the decision to leave the brothers I had shed and drew blood with. That moment was the worst cRPG moment.
