The Upheaval of Sheldon Solow

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Mr. Katz represented his clients in a countersuit seeking compensation for their legal fees, in which they won what Mr. Katz said was one of the biggest sanctions ever awarded in the State of New York, about $1.3 million, a sum they only were able finally to collect in recent months.

“He took a variety of steps, procedural steps, making motions and frivolous appeals, asking for extensions, to delay having to pay out compensation we won over five years ago,” Mr. Katz said.

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Supporters of Mr. Solow don’t deny that some of his cases have rested on shaky legal arguments or worse. These people say that he has fallen victim to bad legal advice and representation, including his long working relationship with Mr. Dreier.

“I think Sheldon was the victim of Marc Dreier and some other lawyers who charm and flatter him into saying yes to things he shouldn’t be saying yes to,” one attorney who has worked with Mr. Solow for years said. “I think Sheldon is really a wonderful guy; he’s a good guy who means well and who has been a target for a long time. In this business, you have to be tough and strong. It’s a shame he has the reputation that he has.”

Mr. Solow hasn’t helped his own case. Always known as an enigmatic and temperamental man, his increasing reclusiveness in old age has made him something akin to a Howard Hughes for the Manhattan real estate industry. In 2010, Mr. Solow ceased coming into his office at 9 West 57th Street for a period of months, and rumors began to swirl about his health. He eventually returned, and there was never an explanation for the episode. But losses like the Citibank and 380 Madison Avenue cases, and past rifts that are now coming to the fore, such as Mr. Cherniak’s suit, may have drained the characteristic fight and brashness that has defined Mr. Solow’s personality and style of doing business.

Tellingly, people who know him say, Mr. Solow has filed few, if any, lawsuits in recent years.

Not all has been bleak for Mr. Solow, however.

Last year, he hired an agency leasing team at 9 West 57th Street from the real estate services company Jones Lang LaSalle. The group’s lead executive, JLL broker Scott Panzer, has appeared to click with Mr. Solow, finally creating a reliable management and leasing team at a building that had seen a succession of brokerage companies hired and fired and, as a result, had accrued hundreds of thousands of square feet of vacancy in recent years. Last year, Mr. Panzer helped Mr. Solow renew the blue-chip investment companies Apollo Global Management and KKR, 9 West 57th Street’s two largest and most important tenants, for high-priced rents befitting the tower’s exclusivity.

“Sheldon appreciates honesty, and he embraces integrity and ethics,” Mr. Panzer said. “The legend is more intimidating than the actual man.”

Perhaps more importantly, Mr. Solow is now working with his son Stefan in handling his company’s affairs. For years, people who know Mr. Solow said that he insisted on controlling his real estate empire alone. Stefan’s participation may be a sign that he is finally cobbling together a sound succession plan.

And, so far at least, the younger Mr. Solow has shown none of his father’s tendencies as a bruiser in the courtroom.

dgeiger@observer.com