A new prime minister, a prorogued parliament and a winter election: the second half of 2019 left the Caribbean community asking what Brexit Britain would mean for those whose belonging had already been questioned once

Briefing
- Boris Johnson becomes Prime Minister on 24 July 2019.
- Parliament prorogued; Supreme Court rules prorogation unlawful in September.
- December election delivers Johnson a large majority; Brexit now certain.
- Windrush compensation paid to fewer than 100 people by year’s end.
- Caribbean community uncertainty about post-Brexit immigration status grows.
On 24 July 2019, Boris Johnson entered Downing Street as Prime Minister and delivered a speech in which he promised to deliver Brexit by 31 October, do or die. His arrival had been anticipated by those who had watched his political career and his record on race with some caution. As Mayor of London, he had maintained a reasonable relationship with the city’s diverse communities. As a journalist, he had written columns that some found entertaining and others found contemptible. His record on issues directly affecting the Caribbean community — the Windrush scandal, the hostile environment policies, the immigration bureaucracy that had stripped British citizens of their rights — was not one of particular advocacy. The Caribbean community in Hackney and Handsworth and Toxteth watched his arrival at Number Ten with scepticism that was measured and specific.
The second half of 2019 was dominated by Brexit. Johnson prorogued parliament in September, an act the Supreme Court ruled unlawful. He negotiated a withdrawal agreement, had it endorsed by a December election in which the Conservatives won an 80-seat majority, and set the date of Britain’s departure from the European Union. For the Jamaican and Caribbean community in Britain, Brexit was not primarily a trade or regulatory question. It was a question about what kind of country Britain was becoming, and what it meant for people whose right to be there had already been challenged, contested and, in the Windrush case, actively denied.
Brexit and the Caribbean Status Question
The formal legal position was clear: Caribbean-British citizens, like all British citizens, were not affected by Brexit in terms of their right to live and work in the United Kingdom. They were not European Union citizens exercising EU freedom of movement rights. Their citizenship predated Brexit and was not contingent on EU membership. But the Windrush scandal had established, with devastating clarity, that formal legal positions and lived experience were not always the same thing. The Caribbean community had been formally, legally British for generations. And yet thousands had been wrongly classified as undocumented, denied healthcare, lost their jobs and, in some cases, been deported.
The lesson that the community had learned from Windrush was that formal status was not the same as security. If the Home Office could, through administrative failure and institutional indifference, strip documented British citizens of their rights, then the anxieties produced by Brexit — about a future in which immigration control was to be significantly tightened, in which the government had made clear that lower net migration was a priority — were not irrational. Community organisations in Hackney, in Birmingham and in Manchester reported increased demand for immigration advice from people who were unambiguously British but who, after Windrush, were no longer certain that their documentation was sufficient to protect them.
The Compensation Scheme: Fewer Than 100 Paid
The Windrush Compensation Scheme had been operating since April 2019. By the end of 2019, it had paid out to fewer than 100 of the estimated 15,000 people expected to be eligible. The figure, when it emerged in parliamentary written answers, was met with a mixture of fury and exhausted recognition by those who had been warning since the scheme’s launch that it was designed in ways that would prevent most eligible people from accessing it. The requirement that claimants prove specific losses through documentary evidence — losses that had often gone unrecorded, in transactions that were informal, in a period when the state had actively refused to recognise the people making them as legal — was structurally inadequate to the nature of the harm.
Community legal advocates, who had been lobbying for changes to the scheme since its inception, continued to press the Home Office. Some improvements were made. The documentary requirements were eased in certain respects. The government commissioned a review of the scheme. But the pace remained, by the assessment of those working with claimants, incompatible with the age and health of the people waiting. The Windrush generation — those who had come to Britain in the 1950s, 60s and 70s — were now elderly. Time was not a neutral factor in this process.
Jamaica: Elections and Diaspora Connections
Jamaica marked its 57th year of independence on 6 August 2019. The Holness government was managing an economy that had been showing signs of improvement — debt reduction, modest growth, low inflation — while grappling with persistent challenges around crime, poverty and youth unemployment. The annual Jamaica Diaspora UK conference provided a formal space for engagement between the island’s government and its British diaspora, with discussions focused on investment, remittances, cultural programming and, increasingly, the political questions of constitutional change and republic status.
The republic debate had quietened somewhat since its more active phase in the early 2010s, but it had not disappeared. In the context of post-Brexit uncertainty and the continuing Windrush fallout, conversations about what Jamaicans’ relationship with Britain should look like — formally as well as culturally — had gained new relevance. The Jamaican diaspora in Hackney, watching the December election deliver another Conservative government with a large majority and an explicit commitment to taking back control of borders, was drawing its own conclusions.
The Home Office would soon be tasked with implementing the post-Brexit immigration system, the points-based scheme that would, from January 2021, apply to all non-British migrants including those from the European Union. The Caribbean community’s relationship with that institution had been defined, in the preceding years, by scandal and by failure. The question of whether a new immigration system, designed and implemented by an institution that had recently been found to be institutionally racist in its treatment of long-settled Caribbean British citizens, could be trusted to be fair and humane, was one that the community was asking with considerable urgency as 2019 drew to its fraught close.
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