I haven't used the latest version of Telerik, but to my knowledge there is no build in solution for this so you will need to write it yourself.
You can add/overwrite some eventhandlers for the dragBegin(onMouseDown) and dragEnd(onMouseUp). In the dragBegin you should store the current mouse coordinates for future use, javascript array or json in a hidden field would be my choice. In the dragEnd do the same for the 2d coordinate.
Next you have 2 coordinates, and you can draw a line between them by using one of many different jQuery plugins, or write your own (
Wikipedia Bresenham[
^] and plot small divs).
This will however be harder if the listview can be scrolled in, because then you will need to factor in the scroll height of both lists and use some offset calculations.
There might be other/better ways, but this is the way I would probably do it.
Hope this helps you get started :-)