In the 1960s, Air Canada and the Canadian government played a pivotal role in bolstering British West Indian Airways (BWIA) to become the Caribbean’s regional carrier. By 1967, the Trinidad and Tobago (TT) government had advanced $15,255,816 to sustain BWIA’s operations, recognizing the urgent need for fleet expansion and financial restructuring. However, BWIA faced more than just financial challenges. A 1966 memorandum from BWIA’s chairman highlighted critical deficiencies in top management, engineering, planning, and accounting expertise, as well as a severe shortage of experienced pilots. The chairman concluded that BWIA needed a financially strong partner with the ability to provide managerial and staffing support. Acting on this advice, the TT government sought suitable partners, leading to a proposal from Canada on May 23, 1967. The Canadian government, after reviewing BWIA’s situation, proposed a comprehensive corporate association between Air Canada and BWIA. Key elements of the proposal included designating BWIA as the regional carrier for the Commonwealth Caribbean, allowing Canada to acquire up to 49% of BWIA shares, appointing a majority of BWIA’s board of directors, and negotiating multilateral air agreements. The TT government, optimistic about BWIA’s potential, had envisioned it as a regional carrier since 1961, when it salvaged the airline. Despite initial efforts to persuade other West Indian territories to join BWIA, the airline’s transformation into a regional carrier was a complex and collaborative endeavor involving multiple governments and stakeholders.