Unlike the majority of dramas about Churchill, the focus of the series is on the middle of his political career, rather than his specific contributions in World War II. So, the story begins with not just Churchill out of office, but his party out of government: Labour is in power and Ramsay MacDonald is prime minister. Churchill's party, the Conservatives, is led by Stanley Baldwin (Peter Barkworth).
Churchill is restless without anything to do except be in opposition, and he soon alienates Baldwin by his extremely angry opposition to Indian independence, which Baldwin is cautiously in favour of. Churchill courts the support of the two most powerful newspaper publishers in Britain, Lord Rothermere and Lord Beaverbrook, which further annoys Baldwin. In the 1929 Wall Street Crash, Churchill's investments are wiped out, leaving him short of money, and in a further wobble in his fortunes, during a lecture tour of the United States he gets hit by a car in a New York street and is badly hurt.
The combination of the Great Depression and political differences within the country leads Ramsay MacDonald to form the National Government, a coalition government featuring Labour, Liberal and Conservative politicians in the cabinet, including Baldwin and Neville Chamberlain (Eric Porter). Baldwin appears to promise Churchill a place in the government in return for his support, but Churchill doesn't get one, and Churchill ruefully has to admit that Baldwin never really promised him one anyway, and that the general perception of him is that his political career is over.
Churchill struggles to stay relevant. In a fight over tariffs on British exports to India, which form part of the proposed Government of India Act, Secretary of State for India Samuel Hoare (Edward Woodward) finds out through underhanded means that Manchester cotton barons aim to oppose the bill. He manages to persuade them to drop their opposition, with the promises of a few baubles and a knighthood for one of them. Churchill finds out about this, and accuses Hoare of breaching parliamentary privilege. Hoare is on the ropes, but gets out of it by simply not releasing all his papers to the committee investigating the matter. What makes it worse is that although Churchill is genuinely opposed to Indian independence, he also loathes Hoare, and everyone knows it, making the whole thing look like personal animosity rather than a matter of principle.
In 1935, Baldwin succeeds MacDonald as prime minister. Churchill is more powerless than ever, and what's more, his beloved cousin Charles 'Sunny' Marlborough dies of cancer. He becomes depressed.
Then, while on holiday in the south of France, he's approached by a Foreign Office official, Ralph Wigram (Paul Freeman), who's deeply concerned about the German military build-up. Wigram is the first of various officials who start feeding Churchill information about both German preparedness for war and British unpreparedness.
Churchill starts to raise the issue in the House of Commons, to the displeasure of Baldwin and Neville Chamberlain, Baldwin's Chancellor of the Exchequer. Then arises the matter of King Edward VIII's intention to marry his lover, the American divorcee Wallis Simpson: Baldwin and the rest of the government are dead against this, because Edward as head of the Church of England isn't allowed to marry a divorced woman (the Church not recognising divorce), but Churchill is stubbornly loyal to the King and insists on pleading his case in the House. Churchill's enemy Samuel Hoare lets this happen, knowing that Churchill's popularity will suffer as a result, as indeed it does: Churchill is shouted down by the rest of the government.
Baldwin retires soon after, relieved to be free of the burden of government, and he and Churchill part on respectful terms. Chamberlain replaces him, insisting that he will never give Churchill a cabinet position. Soon after that, the extent of Nazi ambitions in Europe becomes clear as the Germans annex Austria. Chamberlain meets with Hitler and becomes convinced that he can be reasoned with, but few others think so: even Samuel Hoare turns on him. Chamberlain enlists a new sidekick in senior civil servant Sir Horace Wilson, who tries to keep Chamberlain's policy of appeasement on course. But Hitler proves to be a different sort of politician from anything Chamberlain is used to, promising Chamberlain one thing in person and then breaking his promise the next day. Chamberlain admits that Hitler cannot be reasoned with, and pledges the UK to come to the aid of Poland, should it be invaded by Germany. Sure enough, the Germans invade Poland, and Chamberlain announces that Britain is at war with Germany. He meets with Churchill and offers him his old job from World War One: First Lord of the Admiralty. Churchill accepts, and tells Chamberlain that Britain and its allies will defeat Germany.
The Wilderness Years is notable for both its detailed and fairly accurate representation of a part of Churchill's career; its relative honesty about the less attractive sides of his character, such as his devotion to imperialism and his contempt for the cause of Indian independence (although it softpedals his almost manic hatred, at this period, of anything even slightly resembling socialism); and for Robert Hardy's charismatic, BAFTA-nominated portrayal of Churchill. Its impact was such that there wouldn't be another Churchill-centred TV drama until 2002's The Gathering Storm, starring Albert Finney, which is very much a potted version of The Wilderness Years minus the bits where Churchill comes over in a bad light.
Hardy became so associated with playing Churchill that he went on to play him as a supporting character in three more 80s dramas: War and Remembrance, The Woman He Loved, which was about the abdication of Edward VIII, and Bomber Harris, about the leader of RAF Bomber Command, Arthur Harris. (Later in life he played Churchill again, twice.)
Winston Churchill: The Wilderness Years provides examples of the following tropes:
- Anti-Villain: Baldwin, who is not convinced that there will be war with Germany and who's exasperated with Churchill's constant calls for military build-up in Britain. With hindsight, it comes across as complacency on his part.
- The Cassandra: Deconstructed. Churchill repeatedly produces evidence that Germany is arming itself for war, and plenty of people agree with him, but the people who really need to agree with him (Baldwin and Chamberlain) have their own reasons for not doing anything about it (Baldwin thinks that Britain can't afford to arm itself for a war that may not happen, and Chamberlain believes that Hitler is a reasonable man who can be compromised with) and Churchill gets depressed that his warnings are being unheeded.
- Cigar Chomper: Churchill is seldom seen without one. The end titles roll over an image of his cigar smouldering away in an ashtray.
- The Dragon: Samuel Hoare is this to Stanley Baldwin, and then to Chamberlain, until he has his Reformed, but Not Tamed moment.
- Failure Hero: Ralph Wigram, whose sense of doom about the scale of the German military build-up causes him to commit suicide.
- Impoverished Patrician: Churchill comes from a distinguished family (his ancestor was the first Duke of Marlborough, whose biography Churchill is writing during the series) but he lives far above his means and is constantly running out of money.
- Ineffectual Sympathetic Villain: Neville Chamberlain.
- Jerkass Has a Point: Baldwin is absolutely right, on constitutional grounds, to oppose Edward VIII's desire to marry Mrs Simpson. Churchill, who supports the King, is blinded by his monarchist tendencies.
- Kavorka Man: Lord Derby, who's large and pushing 60, but when one of the Manchester cotton men goes to his hotel room to pass him secret information, is seen to be entertaining a young blonde woman clad in lingerie.
- Kid Has a Point: About halfway through the series, a group of schoolboys ask Churchill questions about his career in politics, and one of them innocently observes that his career is now over. Which, given that he was formerly Home Secretary and First Lord of the Admiralty, and is now over 60 and just an MP, is entirely reasonable.
- Opinion Flip Flop: Clementine gives Winston a The Reason You Suck speech about how selfish he is and how everyone else in the family has sacrificed themselves in one way or another, to support his political ambitions, which have led him to irrelevance and powerlessness at the age of over sixty—and then turns around and tells him that he has to go on, and they all believe it'll happen.
- Politically Incorrect Hero: Churchill won't entertain for a moment the idea that India ought to be independent.
- Reformed, but Not Tamed: Samuel Hoare spends the entire series being a scheming Jerkass opposed to Churchill, until he becomes convinced that Germany really is a threat, whereupon he becomes a Jerkass to Chamberlain instead.
- The Reliable One: Brendan Bracken, to Churchill. When Churchill loses his journalism gig with the Evening Standard and is facing bankruptcy because of the loss of his American investments, Bracken finds a friendly businessman who will cover Churchill's losses and gets him a new gig writing for the Daily Mail.
- Surprise Car Crash: Churchill gets out of a cab in New York City and is hit by another cab.
- We Used to Be Friends: Churchill and Bracken, after their falling out. Subverted in that they make it up.
- "Well Done, Son" Guy: Churchill is this to Bracken, to the extent that Bracken has a picture of Churchill in his home and tends to ask people if they think that there's a resemblance between them. Churchill takes this to be an implication that Bracken is his illegitimate son, is not pleased, and falls out with him.
