Trump's Apprentices? Real Estate's Biggest Jerks

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There are plenty of real estate tycoons, property owners, and developers resorting to jerky moves to keep their real estate dealings running smoothly. Is it any surprise that some of these "schmucky" situations, as Business Week reports, are no big whoop to those who practice them?

Open practitioners like Donald Trump label their one-sided deal-sweeteners as "jerk insurance," which turns out to be a commonly used term for a widely spread practice.

"Jerk insurance" aside, any talk of unpleasant real estate doings gets HousingWatch thinking about all the jerky things real estate honchos do and have done. We've compiled a list of some of the magnates most notorious for being dubbed jerks by anyone from a tenant and business partner, to an ex-wife or brother-in-law.
1. Donald Trump
Easily the most infamous of the bunch. The real estate mogul and reality star is either hated or loved, but regardless the fantastically coiffed brute loves the attention. Bankruptcy many times over won't stop the gawdy, arrogant and often rude Trump. It's likely he isn't just his own biggest fan but also probably the president of his own fan club. Face it: He's too good at keeping relevant. Who else is as good at exacerbating a fight with Rosie O'Donnell or spinning a relationship with Jesse James to stay in the press? Always adding fuel to the fire. Trump's most recent offense: Trump SoHo, a monstrous high-rise condo hotel that's invaded the quaint cobblestoned streets of SoHo.

2. Charles Kushner
It's been four years since the New Jersey real estate magnate turned Manhattan magnate was sentenced to two years in prison for tax evasion, witness tampering, and illegal campaign contributions. He'd pleaded guilty to 18 felonies but his quest to seek revenge on his brother-in-law -- who was helping federal authorities in an investigation against him -- was where the real exemplary behavior played out. Kushner did what anyone would do when family backstabs you, he retaliated by hiring a prostitute to seduce his brother-in-law and then sent a video of the dalliance to his sister. Since then Kushner's kept a lower profile but he's bound to be the grandfather of a little "jerk." His son Jared, owner of the New York Observer, recently married fellow jerk Donald Trump's daughter, Ivanka, keeping it all in the family.

3. Harry Macklowe
Currently a victim of the subprime mortgage crisis, it's been reported that Macklowe is done with real estate. But extreme gains and extreme losses are how Macklowe made his fortune. Back in the 1980s, he famously demolished two welfare hotels near Times Square without filling out the required paperwork, or even turning off the gas. Without warning, he went for wreckage. As a result, Macklowe has to fork over $2 million to compensate for his hasty measures. Macklowe's also proven to be something of liar. He famously promoted the Metropolitan Tower on West 57th Street as a 78-story condo when it was only 65 floors. In the late '90s he was again in the tabloids, this time with Martha Stewart. The two were duking it out about tree and shrubbery removal. Stewart won the much publicized battle.

4. Leona Helmsley
She would probably turn over in her grave if she knew she was behind "The Donald" on this list. The now-deceased "Queen of Mean" was the first female to really own the real estate magnate title. She famously spouted, "Only little people pay taxes," after being charged with tax evasion. In testimony from disgruntled employees the public learned of her many properties, of just how difficult she could be to work for and that, despite her great fortune, Helmsley was notorious for nickel-and-diming everyone from store clerks and contractors to assistants and executive staff. Nevertheless, Helmsley was instrumental in helping her husband run a $5-billion empire.

5. Abe Hirschfeld
The late New York real estate developer made his initial fortune building semi-enclosed "open-air" parking garages, but what gave him most notoriety was being charged with attempted murder at the ripe age of 80. Hirschfeld was convicted of criminal solicitation, after trying to hire a hitman to kill his former business partner because of a "survivor take all" business deal between the two. After serving two years of his three-year sentence, Hirschfeld ran for political office, campaigning as "Honest Abe." Fortunately, he lost to Sen. Chuck Schumer. Also infamous was Howard Stern and Gilbert Gottfried's mocking of Hirschfeld, who it appears was quite a long-winded fellow who liked to hear himself talk.

6. Marc Ecko
The rise and fall of the "Ralph Lauren of hip-hop" has been involved some colossally over-the-top real estate transactions. His business partner Seth Gerszberg was quoted as admitting to spending "six years losing $6 million" after they first built the Ecko brand. After a very impressive recovery, it seems Ecko is in trouble again. After a lousy 2008, it was reported that his retail empire is on the verge of bankruptcy (again), and that his company would be departing its extravagant 23rd Street headquarters. No word yet on whether his 30-acre New Jersey castle, on which he's spent more than $20 million in renovations and updating, is on the market.

7. Sam Zell
When it comes to making money on properties, no accidental fire or eviction can be too morbid for this feisty Chicago developer. Multi-property owner Sam Zell gained his notoriety for his success at hunting down real-estate bargains. He recently bought three Harry Macklowe properties in New York City for $475 million -- half of what Macklowe paid in 2007. He's also quite proud of the nickname "grave dancer" that haters gave him for "dancing on the skeletons of other people's mistakes."

8. Simon Taub
The millionaire made real estate news a few years ago as one half of the real-life "War of the Roses" couple. Unwilling to give his wife a divorce, he convinced a judge to divide his million-dollar Borough Park brownstone in Brooklyn, N.Y., in half, because he didn't want his wife to keep it. The home was split with a Sheetrock wall. Taub who owns several other buildings famously said: "Over my dead body, this house she is not going to get. I will fight for this house with nails and teeth. She will never have it. If she thinks she can stay, then she has to fight until she's 70." Meanwhile Taub, who has claimed bankruptcy, collects hundreds of thousands of dollars in rent from the tenants in his Williamsburg properties.

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