- Seeing Indiana Jones as an old, broken man, desperate to share stories of his glory days to help somebody, anybody, and who is ignored by everyone he meets. His days of adventuring, fighting nazis, and finding the Ark are long gone, and the world has moved on without him. It is now the plastic, artificial, superficial world of early-'90s yuppies with nothing better to do than kvetch about stock prices and fashion, leaving him truly alone.
- Combined with Harsher in Hindsight in the China episode. The last time we chronologically see Indy's mother, she's tearfully caring for little Indy as he's afflicted with a bad fever that almost kills him. Dang. At one point, Indy flat out asks his mother if he's going to die, "like Susie", his sister who died as a very young child. Anna reassures him he won't, but you can see how uncertain she is throughout the episode that she won't lose both her children.
- In "Petrograd, July 1917", Indy befriended a group of young Bolshevik students who decide to join the Russian Revolution. He was unable to stop them from marching into an ambush. One of them died from a gunshot wound.
- Indy's dawning horror during the Treaty of Versailles is going to lead to an even worse war in the future. The fact he's utterly helpless to influence the events happening around him is one of the most depressing moments in the series.
- In the unaired episode "Princeton, 1919" Which became the second half of "Winds of Change" in the recut Indy finally returns home to find his father sitting at his desk, practically where Indy left him, and acting like Indy had simply been gone overnight instead of three years, during which time Indy was fighting in World War I under an assumed name and therefore would have no idea if his only son lived or died. It's not hard to see where Indy got the idea that his father didn't care for him.
- The off-screen death of Indy's childhood governess; after returning from the war and Indy finding out that she passed away, leaving him a farewell letter.
Tear Jerker / The Young Indiana Jones Chronicles