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1929
 
    
In the general election Harold Macmillan loses Stockton-on-Tees to the Labour candidate, Frederick Riley       
1929
 
     
Harold Macmillan's wife begins a long affair with Conservative MP Robert Boothby, but Harold Macmillan decides against divorce        
1931
 
    
Harold Macmillan recovers the parliamentary seat of Stockton-on-Tees       
1938
 
   
Harold Macmillan publishes The Middle Way, outlining a practical course of political action largely based on the ideas of Keynes      
1938
 
     
After Chamberlain's Munich Agreement, Harold Macmillan becomes a prominent member of a Conservative minority opposing appeasement        
1940
 
    
Winston Churchill gives Harold Macmillan his first ministerial appointment, in the Department of Supply       
1940  May 10
 
Narrative history in HistoryWorld     
After the German invasion of the Netherlands and Belgium, Winston Churchill replaces Chamberlain as the British prime minister       
1942
 
   
Harold Macmillan moves to the Colonial Office, as under-secretary      
1942
 
    
Churchill gives Harold Macmillan an unusual job, negotiating on behalf of the British government in north Africa and reporting directly to Churchill       
1943
 
    
Harold Macmillan reveals his diplomatic skills as a go-between at the Casablanca Conference