Losing fish is often... usually the most memorable part of a trip. The experience is so common for me I can hardly recall the biggest, most disappointing of them. But I do have a couple that my brother lost that I'll never forget. The first was a big brown he hooked on the White River. We drifted over the steep drop of just above Crooked Creek when his rod tip jerked into the water. At first I thought no big deal I'll just turn on the trolling motor, hold the boat in place while he deals with the fish. It looked like a good plan until the fish swam over the drop off and started through long gravel flat upstream. Dan did his best to turn the fish but the gavel flat is hundreds of yards long and the fish seemed to panic. This was black in the day when we would bring down our beater 9.9 hp. outboard and rent river jons. The motor was terrible about flooding if you didn't pull, choke and sweet talk it. I must have done something wrong, the thing wouldn't start we had no chance unless we could chase this fish. Two thirds of the backing was out of the reel when it was obvious he'd have to try to turn the fish or risk losing the line.
The other was in southern Illinois. We were having an hoot pulling big bluegill off of deep beds with our spiders. The biggest bass either of us had ever seen took a hooked gill and all heck broke loose. We have this happen fairly often but this dude would let go of the bluegill maybe it was wedged in its mouth or the spider hook got a grip on a piece of jaw bone. After several jumps and nearly netting it a couple of times a stunned and glossy eyed 8" bluegill poped out. Probably would have been the fish of a lifetime.