Thanks everybody for the help! Here is what I ended up with:

USE DiabloLootSystemClone

Go

DECLARE @counter int

SET @counter = 1

WHILE @counter <= 1000

BEGIN

INSERT ChestItems

SELECT c.ChestID

,i.ItemID

FROM Chests c

CROSS APPLY (SELECT TOP ((ABS(CHECKSUM(NEWID())) % (c.ChestTier * 2)) + 1)

Items.ItemID

FROM Items

WHERE Items.ItemTier = c.ChestTier) i

WHERE c.ChestID = @counter

SET @counter += 1

END

GO

I was having a problem setting the foreign keys on the Items and Chests tables and I'd appreciate some feedback on my implementation. I just ended up creating triggers to set them from the inserted table:

CREATE TRIGGER uAddItemsFK ON ChestItems

AFTER INSERT

AS

BEGIN

UPDATE Items

SET

Items.ChestItemsID = i.ChestItemsID

FROM

Items it

JOIN inserted i

ON it.ItemID = i.ItemID

END

GO

CREATE TRIGGER uAddChestsFK ON ChestItems

AFTER INSERT

AS

BEGIN

UPDATE Chests

SET

Chests.ChestItemsID = i.ChestItemsID

FROM

Chests c

JOIN inserted i

ON c.ChestID = i.ChestID

END

GO

Thanks Again, everybody!