Pamela Churchill's marriage to Randolph worsens as his gambling, drinking, and reckless spending keep generating debts that his income cannot cover. Pamela asks Winston Churchill for help, and he agrees to pay the couple's bills only if no new debts are incurred, but credit purchases and delayed invoices make that promise impossible. Pamela is then publicly humiliated at Harrods when she learns her credit has been cut off, and she returns to Downing Street in tears.

The financial crisis exposes long-standing family tensions around Randolph. Winston has repeatedly warned Randolph about debt and his habit of insulting people, though he still writes as a loving father. Clementine is less forgiving: she sympathizes with Pamela, admits she distrusts Randolph's behavior, and fears he will someday seriously embarrass his father, especially when drink makes him quarrelsome and volatile. In October Randolph transfers from the 4th Hussars to a new commando unit in Scotland, only to discover that his former fellow officers are relieved to see him go.

With Randolph away, Pamela tries to build an independent household instead of remaining at Chequers on the Churchills' charity. Brendan Bracken finds her a cheap rectory in Hitchin, and Pamela plans a family home there with baby Winston, Diana Churchill and her children, and Nanny Hall. War conditions complicate every practical step: workers disappear, materials are scarce, evacuees fill the large house, and even low rent does not prevent high running costs. Pamela remains affectionate toward Randolph in her letters but also pleads with him to control his spending while he trains among wealthier men.

On October 14, bombs fall near 10 Downing Street during dinner, blowing out windows and destroying the kitchen and a sitting room; the Treasury is also badly damaged, and the Carlton Club takes a direct hit, though its diners narrowly escape serious injury. As the government prepares to withdraw to Chequers, Winston abruptly realizes the cat Nelson has been left behind and orders the convoy back so the frightened animal can be rescued before the journey resumes.

On October 19, John Colville drives back into Whitehall under bombing, sees the fires that can guide enemy aircraft, and dodges incendiaries before reaching No. 10 and sheltering in Churchill's reinforced dining room. At Chequers that same night, Winston sits in a rare state of exhaustion and discouragement with Pug Ismay, weighed down by the failed Dakar expedition, mounting U-boat losses, and relentless raids. Then his mood suddenly reverses: he leaps up declaring that he can do it, summons lights and secretaries, and recovers the energy that has sustained his wartime leadership.