Of all Chekhov's plays, The Cherry Orchard is most marked by the coming revolution. The fate of the old Ranevskaya family estate marks the crumbling of an old aristocratic order. Transposing it to a deeply divided America – divided over race and by class, between Donald Trump and Hilary Clinton – writer and critic Bonnie Greer suggests a new revolution is looming into view.

She turns the Ranevskaya estate into the Hotel Cerise, a once glamorous holiday destination for aspiring African Americans, now fallen out of fashion and into disrepair. Inherited from a white slave master generations earlier, it's now the property of Anita Mountjoy (Ellen Thomas), a bouji black matriarch whose wealth has insulated her family from the realities faced by many black Americans. Arguably, the Mountjoys are part of the problem: part of a wealthy elite in an unassailable economy. This hotel built "by us, for us" is now out of reach of its intended clientele, and their cherry orchard is staffed by undocumented migrant workers, presumably underpaid and off-book. Operations manager Karim (Abhin Galeya), an aspiring Latin American, has his own rescue plan for the property. He's lined up a load of investors ready to turn it into a global brand, trading on its history by exoticising it.

Set in the weeks leading up to the election, the final phase of Barack Obama's presidency, The Hotel Cerise frames a wide-ranging debate over racial politics. Alexis Rodney's teacher Toussaint can reclaim his African name and preach Malcolm X-style resistance, while Corey Montague-Sholay's shirty employee TK proclaims his patriotism after seeing his best friend killed in Afghanistan – yet both are driven by the same Black Lives Matter movement, while both disagreeing with its methods.

Both mourn the black deaths on the streets – each of them, to Anita's mind, a presidential assassination by proxy. Greer encompasses the spectrum of attitudes around America's retreat on race: the way the hope around Obama's election eight years ago, which seemed to herald a "country healed," has given way to a civil war of sorts. The threat of Trump's election hangs over the sawing down of the cherry trees outside; both dismantle something hard-won and precious.

Too often, however, there's a mismatch between the play, its people and its politics. In finding contemporary equivalents, Greer reduces rich, rounded characters to one-note political standpoints. Where Chekhov's act out of their convictions and characters, Greer's are largely pulled along by plot. None of them feel like real people, still less contemporary Americans, in their actions, and, accordingly, the emotional heft of the play – that minor key quality tinged with loss – feels reedy and thin. Ellen Cairns' flimsy design doesn't help much. When even the hotel itself feels unreal – and not just because the décor is a fairytale forest of copper cornicing – its hard to invest in the idea that anything's at stake. The idea of America is; the Hotel Cerise, less so.

The Hotel Cerise runs at Theatre Royal Stratford East until 12 November.