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Should you be punished for old social media posts?

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I want to open this up with a quote from a recent article @ Polygon:

"Here’s a thought that may or may not scare the living bejesus out of you: Every forum post, every tweet and every Facebook post you’ve ever made gets collected into a giant ball of garbage that is chained to you, no matter how hard you run. The second you begin to write something online somewhere, you begin to chronicle your own history in a way that is unlikely to bring you anything positive. Instead, it comes with the potential to take everything away."

Recently we're seeing a growing number of instances involving varying degrees of people (celebrities, comedians, sports personalities, politicians, and most recently, a former Verge writer turned NYT editor) receive criticism for past tweets and/or social media posts. This criticism is not only at times - career ending, but it often follows them in some way for the rest of their lives.

I wanted to hear what others think about it. Should a person be judged on their past posts? Should it be looked at on a case by case basis? Is it right to dig through someone's past and expose tweets of a potentially controversial nature? I've also noticed that even if something is deemed OK, the damage is often un-reversible as a quick google search will forever mark you as "the person that said that thing".

I'm sure that I myself have written things in the past that I wouldn't want taken out of context. We all have made jokes unrepresentative of who we are as people or what we believe.

What do ya'll think?