Parenting

The main problem I have with parenting is discipline. I make plenty of rules and enforce them, and, luckily, I have rule-following children for the most part. The problem is that I like to make my children happy. Tucker has probably received less discipline than the other two. He's the most stubborn of the kids, he's the third so I have less energy to fight with him, and, frankly, he wears me down.
The latest discipline situation revolves around an iPod. Tucker is ahead of the iPod game. He had a shuffle when the original one was out. Then he got a Nano. Next he received an iPod touch for his birthday. The iPod touch now has a spider web-type crack across the screen. It doesn't work well with headphones any more, which is fine because every pair of headphones he gets are chewed up by the cats. Something about the headphones attract the cats. They don't chew on much, but they love headphones.
As many iPods as Tucker has had, he's had twice as many headphones. He leaves them hanging from the computer and the cats get to them. He has also borrowed many pairs from me, Earl and Grace and we've seen those get chewed up too.
Last week before school, Tucker asked if he could borrow my iPod. I have had one iPod. It's a little green shuffle that clips onto my shorts when I run.
I handed it over and he stuck it in his backpack. The next morning when I got ready to run, I realized I didn't have my iPod. I went into the bedroom and looked at the bedside table, thinking Tucker might have listened to it as he fell asleep. Then it would probably be dead, but at least I'd have it. Tucker woke up and I asked where it was.
"I'll get it in the morning," he said.
"This is my morning," I said then went on a run without it.
The weekend passed and I asked Tucker again where it was. He said he put it in the basement beside the computer.
That day, I found the tiny inside of an earphone on the floor by the trashcan.
Sunday night, after a day of fighting about whether he had to go to swim team and whether he had to go to confirmation class, I laid out the boys' money for the week. I give them money so they can buy lunch (or they can pack) or use for spending money.
Tucker shaved off the burgeoning goatee on his chin and came up to show me. He was trying to make amends for all the fighting and the threat of no Xbox.
"Go get my iPod," I told him since I planned to run in the morning.
He brought it to me. The headphones had been chewed up and torn apart.
I took his money from the counter and told him I would use it to buy more headphones. He could have any money that was left over after the headphone purchase. He went to bed without speaking to me.
I know that it's the right thing to do -- make him pay to replace the torn up headphones, but I hate that he's so unhappy. Hopefully, he'll be more responsible with other people's belongings after this, but it's no guarantee.
How about you? Do you ever remember being punished for something that actually made you change your behavior? Does an object lesson like this work? Have you ever punished your kids for something and seen it make a difference in their behavior? I need some hope here.