Singapore, once under 144 years of British rule since its establishment by Sir Stamford Raffles in 1819, became a part of Malaysia in 1963. This union came about after the merger of the Federation of Malaya with former British colonies, including Singapore, marking the end of British colonial rule in the island state. However, Singapore's inclusion was controversial due to its large Chinese population, which threatened the racial balance in Malaysia. Politicians from Singapore, such as David Marshall, had previously sought a merger, but concerns about maintaining Malay political dominance kept it from realization. The idea of merger gained traction, largely due to fears of an independent Singapore potentially falling under hostile influence and the rising nationalistic tendencies of neighboring Indonesia.

Despite initial hopes, political and economic disagreements between Singapore and the federal government of Malaysia began to surface. The Malaysian government, led by the United Malays National Organisation (UMNO), and Singapore's People's Action Party (PAP) had conflicting views on racial policies. UMNO emphasized special privileges for Malays and indigenous populations, while the PAP advocated for equal treatment of all races. Economic disputes also arose, particularly over Singapore's financial contributions to the federal government and the establishment of a common market.

Racial tensions escalated within the union, culminating in the 1964 race riots. The Chinese in Singapore were discontented with the Malaysian government's affirmative action policies favoring Malays. This discontent was further inflamed by provocations from the Malaysian government, accusing the PAP of mistreating Malays. Major riots broke out in July and September of 1964, disrupting daily life and causing significant casualties.

Externally, Indonesia's President Sukarno was vehemently against the formation of the Federation of Malaysia. He initiated a state of "Konfrontasi" or Confrontation against Malaysia, involving both military actions and subversive activities. This included an attack on MacDonald House in Singapore by Indonesian commandos in 1965, which resulted in three deaths.

The combination of internal discord and external threats made Singapore's position within Malaysia untenable. This series of events and challenges eventually led to Singapore's exit from Malaysia in 1965, allowing it to become an independent nation.