Biggest fail I have seen was when we were young. We had my dad, and 5 youngans on a little fish hawk, including me. My brother pulled back to cast a daredevil, gave er a good whip out there, but got snagged up ... on dads ear. He pierced him perfectly. Right in the ear lobe. Was painful watching him pull it out, but he gave a yank, and kept on fishing.
I am notorious for leaving crankbaits all over the bow of my boat when pitching DL. I once holes myself past the barb on one and had to push it through/snip it off and pull it out. Pard did the same on one and passed out when the blood started. The pass-out happened while he was passenger in the truck as it was being backed down the boat ramp, glad he wasn't the backer-upper. Once saw a guy get 2 or 3 (can't recall which) of the barbs on a treble hooked to his finger while the other treble was still hooked to an irate and energetic ~3-4# pike.
I took dads old Yar Craft one day and didn't know the livewell leaked until I couldn't get it up on plane, bilge ran for ~30min.
In the early 2000's I had a Ranger 681vs. The fit/finish was great but it's performance in waves wasn't. There was no "cruising" in that boat. You either ran wide open trimmed to the max or just up on plane with the motor trimmed all the way down. We were wide open on a very nice and relatively calm day when I ran across where several boat wakes were coming together. I made it over the 1st one fine but I speared the 2nd @ ~40+ mph. I saw my trolling motor disappear in a wall of water and ducked behind my single counsel. My passenger however took the full brunt of that wave and it darn near washed him out of the boat. It's was embarrassing.
While on a good Lindy/bouncer bite I had what I assume was one fish that wouldn't bite. I missed a fish 3 times within ~30' worth of trolling. I got mad, said something along the lines of "filth, flarn, flarn, filth, flarn!!!!" (Which is funnier if you've seen Eddie Murphy "Raw". I slammed my rod down only to watch it bounce right into the drink. I reached for the rod, my head, arm, and one shoulder were under water but I did catch it. I broke and eyelet and bent the main spindle on the spinning reel. Passenger who was also the guy I nearly washed out of the boat thought it was awful humorous. I was embarrassed again.
While taking my cousin on his first Canadian fishing trip to LOW, I tried to show off my knowledge of the lake and all the sights I'd found on that stretch of water and managed to misjudge a spot on the lake I'd been through hundreds of times by about 30 feet. I took out my lower unit with a Big Rock on DAY NUMBER ONE!!!!!!!!!!!!! So my cousins first Canadian fishing trip consisted of fishing of the dock for the first 2 days while I spent 4800 bucks getting my motor rebuilt. We still talk about that epic blunder to this day and laugh at it. It wasn't so funny at the time though.
Buddy of mine (yesterday) dropped a crankbait in the bottom of the boat... i bent down to pick it up boat rocked 1 trebel hook stuck in the carpet the other went past the barb into my finger... hadto push Iit through and clip it off... the only time I've done that in 33 years of fishing and i think i can wait to never do it again (didn't pass out but was glad the nephew brought some beer)
Those South Bend hook removers work.... really, really well.
The fail that has had me the most nervous was when me, dad and an uncle were a good 9 miles out and downwind from our ramp on Lake Erie and we had caught our last fish and headed back. Livewell had been left on and overflowed. When I throttled up into the waves; felt a shimmy n shake and motor began to shake- blade sheared off at hub from the extra weight I assume. We managed to remove everything and put on the spare prop and not drop anything in the 25' of water we were in.
Fishing the Red when I was about 13-14 years old. We used to use old spark plugs out of our snowmobiles for weights. I got snagged up and had 20lb test on. I stretched and stretched that line and it wouldn't break. It finally pulled loose and I took a J8 plug right to the kneecap.
Similar scenario. Not many boats around tho. Got done going and realized, I had no tp on the boat ... So there I sit, hangin out. Decide to rip the hood off of my sweatshirt. Job done. Go back to casting daredevils, still flustered from my epic deuce. 1st cast, catch the hood ...
To this day if I'll get asked 'where's your hood' followed by an enormous giggle. Almost 20 years later.
Boat- Fishing by myself (and my dog) one day on the river. Caught a limit of fish and headed back to ramp. Weather was also moving in, and began to rain steadily. Got to ramp, grabbed pickup and trailer, and backed er down. I had the pickup running and dog was in cab of truck. I get get on dock, hop in boat and untie. Now, maybe I should not have untied, but the motor had ran absolutely perfect all afternoon, as well as every single outing before this one. One pull start every time. As I am drifting slowly away from dock, I cannot for the life of me get that motor started.
Pretty soon, I am about a mile downstream. Pickup still running, and pooch still in cab, and me wet. Unfortunately for me, there was only one other boat out that day, and was nowhere to be seen. I cranked and cranked and could not get it going. Panic mode setting in a tad at this point. Probably flooded after awhile, but still not sure why it did not start after those first couple pulls.
Finally stopped raining, and after what seemed to be 2 hours (more like 15 minutes); all of a sudden I hear a boat in the distance. Was never so happy to see another boat in my life! Haha. Flagged em down and they towed me in. Loaded up boat after a big thank you to the towers. After a long ride home, I had to hook boat up to garden hose. Wouldn't you know it motor fired on FIRST pull! Just glad there was another boat, would have made for a completely miserable day! Haha.
Shore: Fishing for pike on Lake Sak in the spring about ten years ago. Was way back in a bay and wanted to get to a shoreline/point that was on the other side. After a long hike around, I decided to take a little shortcut through the way end of the bay what in what I thought would be just a little muddy. After debating, my buddies took the long way around (smart choice). Bound and determined to get to the "spot" faster....I started to walk across with two handfuls of fishing gear and got about 1/2 the way across and sunk in halfway up my shins. I knew when I first started the run, it was not going to end up good for me. No turning back after I started. That mucky crap was like quicksand. Not good. Dropped my tackle box in mud after trying to keep balance. After getting mud pretty much all over myself, I wiggle my legs loose, but lost my shoes in the process. No extra clothes, but buddy had extra pair of boots. Was not very prepared that day, went after school; didnt have all my normal gear. Proceeded to fish on and lick my wounds. I still catch some crap for that one. I learned a very wise lesson that day. DON'T BE STUPID.