Early career Kwek's father soon entrusted him with Hong Leong's investments, after determining that he was adept at striking deals. In the late 1960s, amid rising tourism, the Singapore government began encouraging developers to build more hotels in the country. Hong Leong won a tender in 1968 to build its first hotel in Havelock Road (next to the
Singapore River), with a land cost of S$980,000. The 12-storey, 175-room King's Hotel — whose name was reportedly chosen by Kwek himself because "I knew I would be the king of hotels" — took about S$4.7 million and two years to complete. A second tower with 142 additional rooms was later added to the development. In October 1969, Kwek and two other Hong Leong employees joined the board of directors of the struggling real estate developer
City Developments Limited (CDL). Kwek was tasked with overseeing the implementation of a rescue package that would resolve CDL's cash flow problems. In 1972, Hong Leong acquired a majority share of the publicly-listed company. Following the
1973 oil crisis, Hong Leong assumed full control of CDL's management and Kwek became managing director a year later.
Overseas expansion In 1990, Kwek's father was found guilty of breaching the Companies Act, having improperly authorised a real estate company that Hong Leong largely owned to pay another real estate brokerage. He was fined S$5,000 and made to step down as chairman of both CDL and Hong Leong. Kwek took over both roles, while his younger half-brother Leng Joo became CDL's managing director. Under Kwek's leadership, CDL made its first European acquisition—The Gloucester in London—in 1993. In 1994, CDL acquired the
Millenium Hotel (whose name had been deliberately misspelt by owner
Peter Kalikow) in
Lower Manhattan,
New York City for $75 million. Kwek appointed
Hilton Hotels to manage the 561-room property and ordered that its name be changed to "Millennium". A few months later, Kwek purchased the
Hotel Macklowe, also in New York City, for $96 million. A year later, he acquired an adjacent building occupied by the
Newspaper Guild for $3.4 million and converted it into an extension wing of the Hotel Macklowe, which reopened in 1999 as the Millennium Premier New York Times Square. Kwek assumed full leadership of Hong Leong after his father's death in November 1994. In April 1995, Kwek and Saudi investor
Al Waleed bin Talal Al Saud acquired an 80% stake in the
Plaza Hotel (which
Donald Trump owned 51% of) from a
Citibank-led creditor syndicate. The deal was structured around the assumption and restructuring of the Plaza's substantial debt, which had been incurred following the U.S. real estate market crash in the early 1990s; Kwek and Al Waleed contributed just over $100 million in equity. The transaction valued the Plaza at approximately $325 million, significantly below the $407.5 million paid by Trump in 1988 using largely borrowed funds. To commemorate their purchase, Al Waleed gave Kwek a gold-dipped
AK-47 with its
firing pin removed. Following the acquisition, Trump retained a minority interest and a role in marketing and condominium penthouse development at the Plaza. Day-to-day operations were entrusted to Fairmont Hotel Management, in which Al Waleed held a significant stake. Kwek later described Trump's involvement as limited, noting that operational authority rested with the new owners, while Trump's advisory role was given "to pacify him". In August 1995, Kwek secured a £219 million deal to purchase Copthorne Hotels Holdings, which had 16 hotels across the United Kingdom and Europe, from
Aer Lingus. Kwek's string of hotel purchases worldwide attracted public attention, with Louis Kraar of
Fortune calling him the "Mystery Man" who "pays Donald Trump's allowance". By this time, Kwek was already overseeing a portfolio of more than 50 hotels in 11 countries, making him one of the largest hotel owners globally. CDL's Millennium and Copthorne chains were subsequently merged into one entity,
Millennium & Copthorne Hotels, which was listed on the
London Stock Exchange in April 1996—the first Singapore-based group to secure primary listing on the exchange. In November 1999, Kwek closed a $640 million deal to purchase 47
Regal hotels in the United States, which were to be renamed under the Millennium brand. A week later, he announced that CDL would be acquiring the
Seoul Hilton for $213.5 million.
Republic Plaza Republic Plaza originated in the mid-1980s as an ambitious commercial development in Singapore's
central business district, initially conceptualised by
Jones Lang Wootton and promoted by a joint venture led by Japanese trading and construction firms alongside Australian firm Land Equity. However, in 1987, Kwek's father acquired two key land parcels on the planned development site from
OCBC Bank at S$51.3 million. Following negotiations with the original joint venture, CDL secured a 50% stake in Republic Plaza in 1988, with the remaining interests held by
C. Itoh, Land Equity, and
Shimizu Corporation. In 1990, Land Equity exited the project and sold its 20% stake to CDL for S$19.5 million. Construction commenced in late 1991, with foundation works completed a year later and the superstructure rising through 1993 and 1994. In 1996, CDL bought out the remaining stakes of its Japanese partners for S$47 million. At the opening of the S$650 million skyscraper in January 1998, Kwek, who had taken over the project after his father's death, said: "When the economy was facing a slump in the 1980s, CDL held on to its bold vision of establishing a world-class landmark on the Singapore skyline. Today, our flagship building stands as a testimony to our long-term business strategy and the successful handover of CDL's first-generation leaders to the second generation." At the time of its completion, it was the joint-tallest building in Singapore alongside
OUB Centre and
UOB Plaza, with a height of .
The Sail In March 2002, Pontiac Land Group triggered the Singapore government's "reserve list"—state land parcels not immediately launched for sale but kept available for developers to apply for—for a plot of land in
Marina Bay. At Kwek's direction, CDL entered the race, based on the assumption that
weak market conditions would limit competitive bidding. True enough, no other bidders emerged and CDL secured the site with a marginally higher bid of S$288.9 million, just 3 per cent above Pontiac's offer of S$280 million. The site was designated a "white site", allowing flexible use, and initial plans leaned towards office development, consistent with its location in the Downtown Core. However, amid an oversupply of office space—exacerbated by the upcoming
Marina Bay Financial Centre—Kwek abandoned the conventional approach. A potential pre-sale to
Standard Chartered fell through, reinforcing his view that a purely commercial project would be uninspired and poorly timed. Instead, Kwek announced that the project, later named
The Sail @ Marina Bay, would be a waterfront residential development that would inject life and imagination into a subdued market. It would also be the first major residential condominium in the Downtown Core, as well as the tallest residential building in the country. Initial launches were met with overwhelming demand, with nearly all units sold rapidly despite sharply rising prices. Kwek later reflected: "The Sail is my most iconic residential project and the one which I'm most proud of."
Marina Bay Sands In 2004, the Singapore government announced that it would legalise casinos under a new "
integrated resort" policy, with one integrated resort to be built in Marina Bay and another in
Sentosa. While public response was mixed, Kwek expressed early support for the move and decided to bid for the Marina Bay project. CDL ultimately partnered with
Sheldon Adelson's
Las Vegas Sands, taking a 15% stake in a Sands-led consortium which became a leading contender for the project. Kwek was actively involved in shaping the bid, including advocating for increased hotel capacity and supporting the appointment of architect
Moshe Safdie. Kwek also personally modified Safdie's initial designs. However, in early 2006, CDL withdrew from the consortium, officially citing "some requirements associated with the bid." Kwek continued to provide informal advice to Las Vegas Sands on design and development matters, and its bid ultimately succeeded. He later suggested that excessive regulatory disclosure requirements associated with gaming investments had contributed to CDL's withdrawal. At the same time, he noted that "many members of my family didn't like for us to be involved in gaming and gambling."
Legal affairs On 25 February 2025, Kwek filed court papers to address an "attempted coup" by his son and CDL CEO
Sherman Kwek, who had allegedly acted with several board members and directors to seize control of CDL's board. Kwek claimed that his son's group had hastily made significant changes to CDL's board committees and governance, while bypassing the CDL's nomination committee twice to change the composition of the board. According to Kwek, this violated corporate governance principles. He added in a statement: "As a father, firing my son was certainly not an easy decision. I accept that business decisions are difficult and young people may make business mistakes in their careers and that is understandable, but circumventing corporate governance laws is a red line." However, Kwek later withdrew the case and stated in an August 2025 press conference: "We have put past issues behind us, emerging stronger and more unified." ==Wealth and philanthropy==