Buying the Plaza seemed like it might be a road into the Helmsley sphere, but he fucked that up royally, blamed it on Marla, and he lost it in bankruptcy court. Every landlord and hotelier was laughing his or her ass off behind his back.
They were also laughing hysterically when he tried to get NBC out of 30 Rock. He was stretched thin buying thin optioning the Penn Cantral rail yards (largest available piece of land left in Manhattan). Was giving everything but blowjobs (and we're not so sure about that) to build his Trump (of course) Television City, with NBC as prime tenant.
Saw the Sterns make a bid to get them into the Meadowlands, but was too stupid to see Hartz Mountain was just being the foil to help juice things along. NBC was never going to move, but did want to get the rent down, so the Hartz bid appears. NBC got the rent down, Hartz got something they wanted without having to build anything big, and Trump was shocked that NBC could be so stupid. Claimed they turned down the chance of a lifetime not moving to the beautiful new center that the city had already told him he'd never get all the permits, easements, and other things he would need and would take years to build even if he bribed every city employee he could find.
And, the asshole investor who noticed that when he bought a stock, it would go up for a while. Wow! So he borrowed a few bucks to buy penny stocks, sold on the way up, and bragged about how smart he was. Trouble, was, the ol' Pump&Dump he claimed to have invented had been used since before the Tulip Bulb idiocy. And it was already illegal. Wall street saw it, though, had some fun for a week or two and shut it down before the Feds noticed it.
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