Can I get on some of this sweet action? For $300, I'll go to sleep whenever you say!

Put on an audiobook (free on YT) with stories to listen to. He doesn’t have to sleep but lie as quiet and still as if he was asleep and listening to the stories. I had the same problem as a kid.

sounds like your kid wants quality time with you, sad trying to buy him off when he just wants you to tell him a story. they're not young forever, my oldest is 19 now and know how fast time flies

You are actually lucky he didn’t take the cash. Were you going to come up with $300 ever night? Really bad idea on multiple levels… You are the parent, act like one instead of resorting to bribery. You can take away privileges and that costs you nothing and doesn’t set you up for continued bribery. When my daughter was 4 or 5 years old I showed her on the clock when bedtime was to be. But I anticipated she’d want to stretch it out so I just made the target 15 minutes before my real expectation and then gave her the extra 15 minutes every night when she asked for it. That solved a lot of problems. The other thing was she didn’t like the dark and I had a night light in her room that was moderately bright for a nightlight. Try to understand the real issue and anticipate it. When my children were young I read a story every night at bedtime and it was a good bonding experience and it helped them relax. 9 might be a little old for story time, but it depends on the child… Oh and if child takes medication for ADD that will cause a sleeping problem and you have to be careful when they take the medication.

He’s 9. You’re bribing him with $300 cash? My son is 6 and autistic and has trouble keeping a sleep schedule, but even I know that bribes typically consist of a Kinder egg (it’s how I used to get through grocery store trips and the COVID shot.) Kids don’t need much in terms of bribes.

Maybe something happened that scared him?

And another example of how NOT to parent. You're supposed to be the boss of your kid, not the other way around.