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I have noticed when I transfer a Pokemon holding an item from the 3rd gen games (sapphire, leafgreen, etc) to HG, Diamond, and so on they keep their items. But when I transfer to black/white, they can't keep their items.

I need an explanation for that.
I know the gems for Dialga, Palkia, and Giratina where given to you shortly after you beat the game (black/white).

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The scientist says that you CAN'T transfer Pokemon with items specifically.
I think this is to make sure you can't get overpowering items too early, such as the lucky egg.
Or just gamefreak is being wierd

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Items like heart scales or shards that have no effect on the holder what so ever. Those specifically, I would like to have in my 4th gen games.
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Gen IV differs from V in transferring. So you can't transfer an item over to B/W and B/W2 from a younger gen game.

Source: another question and past experience

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It's to avoid people obtaining items that do not exist in future games, e.g. TMs that are no longer in use (and TMs cannot be held items in Gen V anyway), Masterballs, Exp. Shares, basically making the game much easier for yourself.

Many people used to transfer their rare items from Generation to Generation; in Gen V, your Pokemon will be able to be traded while holding an item (that's how many people trade for evo stones), but you can't do that outside of a generation because Nintendo didn't want people stockpiling rare items and then using them in future games to make it easier.

Even items available in Gen V are not transferrable, because the amount of time involved for coding every item would be a waste of effort. You can obtain most items in Gen V easily (Heart Scales are given once a day by a lady in Driftviel if you show her a Pokemon with the move she asks), and those that you cannot obtain more than a few of, the game was designed to be that way.

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No, you cannot transfer Pokemon with Items. The Game will ask you if the items can be removed so your Pokemon can be transferred anyway. Game Freak did this concept because they want to avoid things to be transsferred that cant be found in Pokemon Black or White, for example TM Dark Pulse.


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