In the 1980s, Wayne Barrett reported on Donald Trump's dalliance with La Cosa Nostra. as did Michael Isikoff in March, and now David Cay Johnston has broached the almost-forbidden subject. He notes
No other candidate for the White House this year has anything close to Trump’s record of repeated social and business dealings with mobsters, swindlers, and other crooks. Professor Douglas Brinkley, a presidential historian, said the closest historical example would be President Warren G. Harding and Teapot Dome, a bribery and bid-rigging scandal in which the interior secretary went to prison. But even that has a key difference: Harding’s associates were corrupt but otherwise legitimate businessmen, not mobsters and drug dealers.
Still, the "liberal" mainstream media (video above from Thom Hartmann from September) has been loathe to look at the organized crime connections of the fellow who has nearly an even chance of being the next President of the United States.
Steve M. identifies a few possible reasons: it seems like old news; The Sopranos, Scarface, and rap music have made organized crime figures into heroes; and the belief "that you can't make a fortune in East Coast real estate without some ties to the mob. We assume he just had no choice."
One of S.M.'s commenters (sdhays) acknowledges those factors but adds
unlike "violent drug gangs" or cartels, "the mob" is made up of white people. Or, at least, that's the way it's thought of. They're the "respectable" organized crime. It even has a civilized name: "organized crime". So it's a "respectable" cultural fixture of the Northeastern US, especially in NYC.
I'll just add to your point of "the mob" being sexy that the vast majority of Americans do not live in a society where they personally experience "the mob's" existence. We experience it solely through popular culture or the national news out of NYC or Boston. It's distant, and almost from a bygone era, "The Sopranos" not withstanding.
So it all comes back to: the media shouldn't say he has "Mob ties". They should say he has ties to violent criminal organizations. Throw "violent drugs" into it, and you might penetrate the national discussion for a few days.
If the message that Donald Trump has been involved in violent crime is continually repeated, it will penetrate the national consciousness for a few days and become a major issue. Connecting Trump to violent crime should not be difficult, especially now that he has scored the full-hearted endorsement of the National Rifle Association, perhaps America's foremost pro-crime organization. The NRA's opposition to legislation preventing individuals on the terrorist watch list from buying firearms is one place to start, and I'd probably substitute "individuals on the terrorist watch list" to "terrorists." Let 'em squeal.
The primary reason Trump's former dealings with the Italian-American mob has been ignored is there is no tie-in. There is no video, nothing visual to make the connection. The next best thing would be linking Trump's associations to violent criminal organizations involved in drugs. That would be devastating, and nearly effective if drugs were not put into the mix.
Organized crime has become somewhat glamorous. However, Americans remain fearful of violent street crime and the people involved in it.