.net - Getting The Highest Owner Of A ToolStripDropDownItem?

I'm currently working on a project in which at one point, the user may right click a button which brings up a contextMenuStrip. I am already able to find the owner accurately from that strip, and manipulate the button clicked as follows:

Dim myItem As ToolStripMenuItem = CType(sender, ToolStripMenuItem)
Dim cms As ContextMenuStrip = CType(myItem.Owner, ContextMenuStrip)
Dim buttonPressed As DataButton = DirectCast(cms.SourceControl, DataButton)

But now for the tricky part. Within this contextmenuStrip, I have a DropDown menu with multiple items in there. I would assume you would be able to work your way up the ladder doing casts like above in the manner of

ToolStripDrowpDownItem > ToolStripDropDownMenu > ToolStripMenuItem > ContextMenuStrip

Unfortunately, when I try to get the sourcecontrol from this menuStrip, it return Nothing. Any ideas on how I can get the button that was pressed from this toolStripMenuItem? My current code is as follows (in which the sourceControl is Nothing)

Dim myItem As ToolStripDropDownItem = CType(sender, ToolStripDropDownItem)
Dim dropDown As ToolStripDropDownMenu = CType(myItem.Owner, ToolStripDropDownMenu)
Dim menuItem As ToolStripMenuItem = CType(dropDown.OwnerItem, ToolStripMenuItem)
Dim cms As ContextMenuStrip = CType(menuItem.Owner, ContextMenuStrip)
Dim buttonPressed As DataButton = DirectCast(cms.SourceControl, DataButton)

how to go about doing what I did in that first method, but just working my way up from further down the ladder?