Mens Shoes: Podcast #717: The Fraught, Relatable Relationship Between Winston Churchill and His Son

Winston Churchill once said of his only son: “I love Randolph, but I don’t like him.” It’s a sentiment many a parent with a tumultuous relationship with one of their children can relate to, and well describes both how Winston felt about Randolph, and how Randolph felt about his father.

My guest today details Winston and Randolph’s incredibly close and yet terribly complex and combustible relationship in his book, Churchill & Son. His name is Josh Ireland, and we begin our discussion with how Winston’s own harsh and neglectful father influenced his decision to be a much more involved and ultimately indulgent family man, and the way he spoiled a son who was already inclined towards appalling behavior. Josh describes the manner in which Winston and Randolph both bonded and fought, and the effect the trouble Randolph caused had on the relationship between Winston and his wife. We then get into how World War II, and the way Winston may have encouraged Randolph’s wife to cheat on him with an American diplomat, affected Randolph’s relationship with his father for the worse. Josh explains the outsized expectations Winston had for Randolph, the points at which father and son respectively realized they’d never be fulfilled, and the lesson to be taken from their story about the cost of parents imposing their own dreams on their children. We end our conversation by discussing why it is that the children of great leaders rarely turn out well themselves, for, as Randolph himself observed, “Nothing grows in the shadow of a great oak tree.”

If reading this in an email, click the title of the post to listen to the show.

Show Highlights

Why was Josh interested in tackling the relationship between Winston and Randolph What was Churchill’s relationship with his father like?Why did Churchill still revere his father in spit of the terrible treatment?How that terrible childhood impacted the future leader’s abilities and ambition Where is Churchill at in life when he marries and has children?What was Winston like a father? Why was the relationship between Winston and Randolph so fraught?What about Clementine, Randolph’s mother? What was their relationship like?How WWII impacted Churchill’s relations with his kids Why did the PM decide he needed Randolph by his side?Randolph’s first wife, Pamela, and how Winston took advantage of themWhat happened after the war? What did Josh learn about fatherhood from studying this relationship?

Resources/Articles/People Mentioned in Podcast

Rogue Heroes by Ben MacintyreHow Churchill (and London) Survived the Blitz of 1940The Audacious Life of Winston ChurchillThe Making of Winston ChurchillThe Winston Churchill School of AdulthoodChartwellStalin’s Daughter