Though today he is hailed as one of Britain's greatest leaders, throughout his career, Winston Churchill was an outsider, accumulating a reputation for bad judgement and untrustworthiness. Only risk-takers and fellow outsiders would back him - but these strong and often feuding personalities proved to be vital to his decision-making in war and peace alike. Winston's Bandits provides, for the first time, a detailed account of his greatest friendships. These friends were Max Aitken, Lord Beaverbrook, a press baron who craved power but only on his own terms; Frederick Lindemann, later Lord Cherwell, an ascetic and quarrelsome scientist who believed in Churchill's intellectual genius; Brendan Bracken, an Irishman from a humble background who reinvented himself as a major force in financial publishing and gave Churchill unconditional support; the young Bob Boothby, who would earn notoriety for adventurous sexual conduct and dubious financial dealings; Randolph Churchill, who was often a disappointment and burden to his father; and Duncan Sandys, who reaped the full benefits of being Churchill's son-in-law in his political career. Together, they were Winston's bandits. This remarkable book explores how Churchill's relationships with these forceful and intriguing sparring partners provide the key to understanding his greatest triumphs and disasters.