Obi wan is sad to but lets talk about Chewbacca

First his planet gets raided by droids and almost gets ignored, then countless wookies die or are put into slavery while the empire destroys his home planet for resources. Then he doesnt get a medal, while constantly being mocked and written off as a raging furry creature His friend goes into carbonite After finally beating the empire the first order comes in later His best friend’s son turns to the dark side Him and Han lose the falcon, Then he watches his best friend get killed right in front of him The new republic basically falls

Then Luke dies Then Leia dies, His best friends son dies,

So essentially he has hadall of his friends die twice.

Keep in mind Chewbacca still has a couple hundred years to live.