Never really had a high-dollar screw-up myself, but I've been on jobs where the following happened:
New school, fire alarm system was not commissioned, but HVAC guys turned on the heating system. Since the fire dampers were closed, they blew up a lot of their ductwork.
3-story motel, addressible fire alarm system. Someone terminated the 120v supply on the screws for the detection system. Every pull, smoke, heat, duct etc. had to be replaced.
Digging a pier for a street light, the guy operating the derrick truck was digging exactly where he was told. Hit a 24" water main and barely got the truck out before the street collapsed.
Trenching around a parking lot for a motel, stinger got hold of the plastic gas line that ran under the (concreted) parking lot. Line was so new, it was not marked by locators. Gas company tried to hit us up for it, but backed down and replaced it (and part of the parking lot) on their dime.
And the Real Biggie: (This is true, I swear!) Old, 3-story house, had been converted to 6 apartments over the years. City got hold of it and was converting back to SFD. Walked out to van parked on street, and found water running along curb. Then more water. And more water. Pretty soon, I had to step out of the torrent. Plumbers were digging in new supply and broke the water main with their bucket. An hour after the city repaired it, they hit two fiber optic lines. Oops. No 911 for 3 counties. And if their day hadn't gone bad enough, here's the real kick-in-the-pants: Coming back from lunch, I turned the corner and saw a blue haze in the air. Thinking someone was burning yard debris, I parked and got out. I immediately was hit by the strong smell of natural gas.
Yep... plumbers hit the gas line. And not just any gas line.... a high-pressure line. Oh, and that's not all. Nearby was a commercial construction site that was doing dirt work. Since they didn't have access off the main streets, they got permission from the city to use one side street for the dump trucks to enter, and another side street for them to exit. No exceptions. So, when the plumbers hit the gas line, they effectively shut that job down 'cuz the gas company closed off all the streets in the area.
So the plumbers were on the hook for the water main break, the 2 fiber optic lines, and the gas line fiasco. That included the repair, paying for the lost gas (yes, they can calculate the amount of gas lost and bill accordingly), as well as the two operators on the job site and 18 dump truck drivers who had to sit for several hours.