First of all, let me explain how the timeline orders the items - the items are sorted by StartDate first and then by Duration. Then, every item is positioned using the following logic - in case there is space for the item in the first row, it is positioned in the first row; if not, the item checks is there is space in the second row to show without overlapping other items; and so on. That is why, in case your items do not overlap, all will be positioned in the first row. In your particular case, five rows are enough in order to show all items and that is why, the timeline orders the items only in five rows. The basic idea behind this ordering, is that the items are displayed as close to the time line as possible.
Currently, there is no easy way to influence the positioning algorithm but we are always looking for customer feedback. Can you explain you idea in greater detail - how do you expect the items to be positioned? It will be great if you can send us a couple of screenshots, demonstrating your idea as well.
the Telerik team
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