I would say my "Iaconelli Moment" would be when I lost what wouldve been my my PB a bass around 10 lbs or so. I was throwing a buzzbait across a weedy point and the fish broke the water with a strike and missed the lure. I saw the fish and my initial though was around a five pounder. I cast back again and brought it directly over the previous strike point. He struck again and this time he was hooked. the point was only 15 or so feet away from my boat (a pond prowler), inexperienced at the time i reeled as quick as possible and the fish was coming directly at me. At about two feet from the boat he made a U-Turn and came out of the water and thats when I saw the "big one" clearly. In mid air he snapped the line and i was just apalled. I threw my rod in the water out of fury. seconds later I said "oh *****" and jumped out of the boat and grabbed the rod, it was a bad day after that needless to say.
