YES

The "type" of association is pertinent.
Examples are like Obama saying that Rev Wright is/was his "spiritual leader , personal friend and mentor(he titled one of his books from a phrase used by rev wright.
Or perhaps a real estate deal being brokered for Obama by a man convicted of crooked real estate deals(Resco)
Or perhaps friendship and business sharing with an admitted terrorist.
It is the "depth" of his associations that becomes troubling.

__________________
"Most people can't think, most of the remainder won't think, the small fraction who do think mostly can't do it very well. The extremely tiny fraction who think regularly, accurately, creatively and without self delusion---In the long run these are the only people that count."Robert Heinlein