re: Rank these events in terms of historical significance

Pearl harbor
Great Depression
Covid ( may end up being higher in the end)
9/11
JFK

Maybe 2008 (not much worse than typical recessions that occur every 10 years or so)

No one cares about Katrina outside the Gulf Coast

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Would rank the Great Depression higher because not only did it occur in the US but also world wide and set up what would become WWII later on

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WWII would definitely be the top of the list, absolutely. If one goes back and says "this wouldn't happen if this wouldn't have happened, and that makes the first thing more important," you could get back to a stock broker stumping his toe and subsequently causing the great depression. I choose to look at the individual happenings. WWII by far.

I'm older than you. 2008 was nothing like the Great Depression, or perhaps the GD wasn't as bad as history writers make it out to be?
Sure, there was a real estate bubble burst and the government bailed out the auto industry, but there was the dot.com bust less than 10 years prior that really knocked the stock market to pieces. Then before that was the 1987 stock market crash. It all depends on where you are working and how bad it really is. For some, the late 2000's were boom years.
People jokingly define a recession is when you have a friend laid off, a depression is when you are laid off.

Pearl Harbor
9/11
Great Depression
JFK Assassination
Katrina
Recession of 2008
Covid

Some of y'all slept thru history classes.

How is Katrina even on this list?

1. Great Depression
2. Pearl Harbor
3. 9/11
4. JFK Assassination
5. Great Recession of 2008
6. Hurricane Katrina

And it's still too soon to assess the overall historical significance of the 2020 Covid-19 Pandemic as it's still happening.

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We’d all be speaking German right now if the D-Day invasion had a different outcome and the German won.

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No, we wouldn't have. Hitler had no imperial aspirations beyond mainland Europe. He desperately wanted peace with the British Empire because he believed them a stabilizing force in the world. I'm not trying to be a Hitler apologist by any stretch, but people need to realize that Hitler had limits to his ambitions and aspirations. He never once considered crossing the Atlantic to invade the United States. He couldn't even if he wanted to because the German surface navy, aside from a few pocket battleships and battle cruisers, was virtually non-existent. You also have to realize that by mid-1944 the German military was a shell of its former self. They were pretty much done as an offensive fighting unit and could do no better than to sue for peace should they have won the Battle of Normandy. And that likely wouldn't have gone over well because they still had the Soviet Union to contend with on the Eastern Front. The disaster at Kursk in the summer of 1943 sealed Nazi Germany's fate. No victory over the Allies on D-Day would have stopped the inevitable collapse of their government.

Great depression and C19. Everything else