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So I'm working in 2nd Gen. trying to get a Lucky Egg and my technique is the I'm in Route 15 using a max repel with a Lvl. 25 Skiploom at the front with a Lvl. 21 Pidgeotto as my thiefer hunting Chanseys like no other. I've ran into quite a few of them and gotten a thief off each time. Now my question is that if Thief works does it tell you? Like give you a message saying that you've stolen a Lucky Egg and if it doesn't does that mean I have to KO the Chansey to find out? Sorry for writing so much and asking multiple questions!

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I don't believe that it gives you a message that you stole an item. The stolen item will appear on the Pokemon who used thief after the battle has ended (I believe) - so thief only works if the opponent has an item and you have no item.
So yes you need to KO Chansey to find out.

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Use the move thief, it will tell you that you find something! Defeat Chansey! and then you will find the item. it is a certain % of finding the ''lucky egg'' mind. You don't get one every time.

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It will inform you that your Pokemon stole an item. It's very important your Pokemon doesn't already have an item equipped or else you won't steal it.

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You sure this is true for all Pokemon games, including Gold and Silver?