Timothy Brown, a former firefighter, sued to prevent construction of the community center so close to the site of the September 11 attacks.

In February 2011, several prospective buyers of condominiums in the building, including French soccer star Olivier Dacourt, sued the developers in federal court, claiming that they had been tricked into buying the condos by the "deceptive" sales figures, and that the number of apartments sold at Trump Soho had been "fraudulently misrepresented."

[18][19] Several years later, the case was described as "a watershed case in the world of condo litigation ... [C]ondo attorneys said that developers are now far more reluctant to disclose sales information to buyers’ attorneys, for fear of legal repercussions if they turn out to be wrong.”[20] Following the 2007–2008 financial crisis, Bailey used the Interstate Land Sales Full Disclosure Act of 1968 to relieve purchasers of Sky View Parc, a $1 billion condominium complex in Queens, of their contractual obligations to purchase, and obtained the largest residential condominium settlement in New York history.

In a well reported familial celebrity case Scarlett Johansson fired her daughter, Melanie Sloan, as her agent and subsequently entered into a realty dispute.

Prior to Ms. Sloan's dismissal, she had entered a contract to buy a two-bedroom apartment on West 43rd Street, Manhattan, New York.

Using the reasoning that she no longer had the funds to purchase the apartment after her daughter had fired her, Ms. Sloan sued the sellers for her entire deposit back.

The tenant, a memorabilia collector, was attempting to sell the white suit John Lennon wore on the cover of the Beatles’ “Abbey Road” album.

The suspension was imposed for undignified conduct (including telling a party suing Bailey's client that he "should commit suicide") and for threatening criminal charges to obtain an advantage in a civil matter.

[37] In 2011, Bailey wrote Finding The Uncommon Deal: A Top New York Lawyer Explains How to Buy a Home for the Lowest Possible Price.

The book gained Bailey the 2012 "First Time Author" award granted by the National Association of Real Estate Editors.

[38] Bailey has written a children’s book, Home, which was named a Silver winner in the category Picture Book/Early Reader by Literary Classics.