[Popman]

My very PC boss once told me I should not use the phrase "tar baby" because it came from a time when African-American infants were tarred and feathered.

Fine example of the "Peter Principle"

How stupid does a person have to be to believe that African-American infants were tarred and feathered???

[Williams]

I thought a "tar baby" meant you are identified with a position so indefensible or offensive that it sticks and you can't get it off of you, like tar. Am I wrong?