To reproduce:
- Click the InsertMergeFiled button before setting the data source.
- Set the data source.
- Click the button again.
- There are no items in it.
 

Workaround:
Friend Class MyRichTextEditorRibbonBar
    Inherits RichTextEditorRibbonBar



    Protected Overrides Sub dropDownButtonInsertMergeField_DropDownOpening(sender As Object, e As CancelEventArgs)
        MyBase.dropDownButtonInsertMergeField_DropDownOpening(sender, e)
        If Me.dropDownButtonInsertMergeField.Items.Count = 0 Then
            Me.dropDownButtonInsertMergeField.Items.Add(New RadItem)
        End If
    End Sub

End Class