[4] Among the structures that had previously occupied the site were two single room occupancy (SRO) hotels at 143 and 149 West 44th Street, as well as residences.

[9][10] The firm of Gruzen Samton Steinglass had been involved in preliminary designs, but that company was replaced by Perkins & Will during development.

The annex was designed by Stonehill & Taylor[7][11] and Kiat Supattapone;[12] it is known as the Millennium Premier New York Times Square.

[17] Macklowe acquired the unused air rights of the Hudson Theatre to make the original tower taller than would normally be allowed under zoning laws.

[26] Within the original hotel building, the two entrances are connected by a passageway running the entire block, which functions as a privately owned public space.

The walls contain Day-Night, a pair of oil paintings by Carlo Maria Mariani, which depict an awake man and a sleeping woman.

[27] When the hotel passed under Millennium ownership, the restaurant space became the Bugis Street Brasserie and Bar, serving Singaporean cuisine.

[36] The rooms' decorations were designed with a black and tan color scheme, cherry-wood headboards, and Art Deco armchairs.

[18][46] A new deck, dressing rooms, and stage rigging were added to the theater, and a projectionists' booth and a Dolby sound system were installed as part of the conversion.

[3] Macklowe paid Mitran Associates $380,000 to demolish four structures at 143–149 West 44th Street during the night of January 7, 1985;[54] at the time, Sol Goldman was selling him the buildings, but the sale had not yet been finalized.

[57][58] Macklowe had been motivated by a desire to avoid a pending moratorium that would have prevented the demolition or conversion of SROs across the city for 18 months, which would take effect on January 9.

[52][56][59] Macklowe had told John Tassi to tell Eddie Garofalo, who headed Mitran, that the buildings were being demolished on Goldman's behalf.

[56] The city government sought to imprison the responsible parties,[60][61] and Manhattan district attorney Robert Morgenthau indicted both Goldman and Garofalo.

[59][62] Morgenthau sent the case to a grand jury, saying the defendants' failure to disconnect utility lines had constituted reckless endangerment.

[59] Macklowe paid a $2 million fine,[63][64] and the city gave the money to the Franciscans, which used it to fund a development for the homeless.

[65] Initially, Macklowe had been planning an office tower for the site, but that had been delayed due to the controversy over the illegal demolition.

[66] Garofalo was found guilty of reckless endangerment,[67][68] but he was given a conditional discharge absolving him from all charges if he did not get in any other legal trouble for a year.

The New York Daily News reported at the time that the moratorium would prevent the redevelopment of the Lenox Hotel at 149 West 44th Street, which stood in the way of Macklowe's project.

[77] A spokesperson for the New York City Department of Buildings said at the time that, since the SRO moratorium had expired, Macklowe was allowed to develop the site.

[79] Macklowe also received $3.3 million in restitution from the city government after the New York Court of Appeals found the SRO moratorium to be illegal.

[73][82] Harrison J. Goldin, the New York City Comptroller, ordered an investigation into the matter, saying Macklowe had signed a legal agreement in which he had accepted the ban.

[84] Koch had given conflicting explanations, first saying the ban had been revoked through legal channels, then suggested that council members did not read the legislation closely.

[37][38] One of the hotel's promotions included an offering of Broadway tickets and a dinner,[27] while another provided personalized bathrobes with guests' initials.

[46] The theater was to serve as an auditorium for independent events,[18] including corporate meetings, fashion shows, and product launches.

[95] The hotel's management wished to attract fashion shows to the conference center as well, despite the relatively small size of Hudson Theatre's stage.

[100] In September 1994, Chemical arranged to sell the hotel to Kwek Leng Beng of Singaporean chain CDL International for about $100 million.

[103] At that point, half of the hotel's revenue came from conferences; the services included a $100,000 charge for broadcasting an event to live attendees at ten other sites.

[109] CDL had requested a tax abatement for the construction of the Millennium Premier, arguing that it was part of the existing hotel because it did not have separate mechanical system and it was connected to the Hudson Theatre at several locations.

The city initially denied the tax abatement, conceding the Premier annex was separate from the original hotel, and the New York Supreme Court upheld the decision.

"[120] The following year, Goldberger wrote that the lobby "is a spectacular interior set within a mediocre new tower of dark green glass on a stone base that appears to have been designed for another building altogether", though the guest rooms were less impressive to him.