In 1988 he ran against Democratic nominee Michael Dukakis.
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Michael Dukakis(when he ran against Bush I)
was portrayed as soft on crime.
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The ad was intended to picture Dukakis as soft on crime, and it worked.
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Dukakis always regretted not fighting back,
a typical Democratic approach to appear above it all or mistakenly thinking it will just die if they pay no attention to it.
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Aspects of Ivy stereotyping were illustrated during the 1988 presidential election, when George H. W. Bush(Yale'48)
derided Michael Dukakis(graduate of Harvard Law School) for having"foreign-policy views born in Harvard Yard's boutique.