Lee later said the establishment of the youth wing reflected concerns by the leadership that the lack of an official channel to engage with the younger generation might lead them to vote for opposition parties and potentially bring the PAP government down.

The handover was largely supported by business analysts, who felt that the importance of the position necessitated the dedication of a full-time minister for Singapore to entrench and promote its role as a financial hub.

Regional economist Song Seng Wun said that with the growing sophistication of the economy and the financial markets' increasing volatility, Lee "may not have the full-time attention" due to his concurrent duties as prime minister.

[52][53][54][55] As part of the Lee government's effort to promote Singapore as an international center for arbitration, the city hosted the leaders of Mainland China and Taiwan for the Ma-Xi meeting on 7 November 2015 and the North Korea–United States summit on 12 June 2018.

As part of the party's leadership succession, the move was widely interpreted as a prelude to Heng succeeding Lee as Singapore's fourth prime minister after the next general election.

Lee's government said that it was necessary to plan ahead for increasing annual recurrent expenses, with Heng Swee Keat saying that the "hike cannot be put off or scrapped" to pay for critical future needs, especially in the healthcare sector.

[62][63][64] In his Budget 2020 speech in February, Heng announced amendments to the GST Voucher Fund Act that would allow grants-in-aid to be given to parents or guardians for infants and children to mitigate their expenses.

[67] Despite concerns by activists and opposition Members of Parliament that the Act would limit free speech under the guise of preventing disinformation, the bill passed by a 72–9 vote on 8 May 2019 after two days' debate.

[71] Social media firms like Facebook expressed concern that the law would grant "broad powers to the Singapore executive branch to compel us to remove content they deem to be false and pro-actively push a government notification to users".

[73][74] Lee and his ministers actively rebutted allegations by overseas media that POFMA is a tool for censorship, saying that "no information or view has been suppressed" as a result of the Act and that the government "has not restricted free debate".

[75] In an interview with The Straits Times, Lee noted that fake news could disrupt society, and that the United States and Europe were struggling to manage the situation, especially in light of alleged Russian interference in recent elections.

[80] With the pandemic pushing Singapore into a recession,[81] the government unveiled four successive stimulus packages intended to keep the economy afloat, the Unity, Resilience, Solidarity and Fortitude budgets.

[82] Following the 2020 Singapore general election, Lee was re-elected in Ang Mo Kio GRC, with the PAP securing 61.23% of the national vote, beginning his fifth successive term as prime minister.

[83] While noting that voters had delivered a clear mandate, Lee wrote in a letter to the party ("rules of prudence") that with the official appointment of a leader of the opposition to reflect ground sentiments for alternative ideals, PAP MPs should expect more vigorous debates and probing questions in Parliament.

[84][85] As a recognition of the Workers' Party's performance in the election and acknowledgement of society's desire for alternative ideas and more robust debate, Lee appointed Pritam Singh as the first official Leader of the Opposition.

[99] The Lee government's policy towards the People's Republic of China has been marked by extensive cooperation in government-to-government projects such as the Suzhou Industrial Park, Tianjin Eco-City and Chongqing Connectivity Initiative.

[100] The China-Singapore Free Trade Agreement, the first of any Asian country with China, came into effect in 2009 and was upgraded in 2018, with new regulations governing e-commerce, fair competition and the environment; Singaporean firms were also granted greater access to Chinese markets, including the legal sector, which has been denied to other nations.

[108] In spite of Chinese pressure and repeated offers of Hainan as an alternative site, Singapore continues to regularly send troops to train in Taiwan under Project Starlight and expects Beijing to respect its right to do so.

[116][117] Singapore has since sought to improve its relations with China, signing a defence agreement in October 2019 to enlarge military exercises with the People's Liberation Army, provide mutual logistics support, and increase exchanges between the two armed forces.

[120] Singapore has traditionally viewed the US as a critical guarantor of stability and security in the Asia-Pacific region and Lee's government has continued that policy, emphasising the US's role as an important counterweight to the rise of China and its increasing military prowess.

[121][122] The two nations have a defence pact[123] dating to the 1990 memorandum of understanding (MoU), which allowed US access to Singapore's air and naval bases and established the Logistics Group Western Pacific at Sembawang Terminal.

[135] Lee was one of the early drafters and a strong advocate of the Trans-Pacific Partnership, which was intended to lower both non-tariff and tariff barriers to trade[136] and establish an investor-state dispute settlement (ISDS) mechanism,[137] and on many occasions urged the U.S. Congress to ratify the deal as soon as possible, adding that not to do so would "affect U.S. standing and credibility" in the world.

To avoid harming the relationship, efforts have been made to isolate unresolved disputes from cross-border cooperation tackling transnational crime, terrorism and drug trafficking; this has resulted in close collaboration between Singapore's and Malaysia's police and security agencies.

[158][159][160] Lee reiterated the legally binding nature of the joint projects, which stipulated compensation to Singapore in the event of a cancellation, but nevertheless acceded to Malaysia's request for an extension to conduct a review.

[161][162] In October 2018, tensions rose when Malaysia extended its Johor Bahru port limits past its 1979 maritime claims into undelimited waters off Singapore's reclaimed Tuas sector.

[164] In April 2019, Transport Minister Khaw Boon Wan and his counterpart Anthony Loke reached a joint agreement to revert to the previous status quo on both disputes.

Prime Minister Goh Chok Tong ordered an immediate investigation into the matter, since although the provision of special discounts or rebates to relatives and associates of directors is permitted under Singapore law, shareholders must approve such transactions.

In 2010, Lee, together with his predecessors, threatened legal action against The New York Times Company, which owns the International Herald Tribune, regarding an op-ed piece titled "All in the Family" of 15 February 2010 by Philip Bowring, a freelance columnist and former editor of the Far Eastern Economic Review.

In response, media rights watchdog Reporters Without Borders wrote an open letter urging Lee and other top Singapore government officials to stop taking "libel actions" against journalists.

[203] In October 2020, Lee took the stand in a four-day trial in the High Court against Leong, who was defended by lawyer Lim Tean, secretary-general of the opposition party Peoples Voice.