I have actually put a fair bit of thought into the biggest tragedy in my life. The real answer is that I haven't really ever had to deal with tragedy in the normal sense of the word. You could probably say I'm one of the luckiest people ever in that regard. I grew up in Boulder, CO. My parents are married, and have always had more than enough to support my brother and I. They made sure we got to play the sports we wanted, and they are hands-down the most supportive parents you have ever met. I went to great schools, and a great university to finish it off. All four of my grandparents saw me graduate college. Now I race for a living.
Now, don't get me wrong, bad things happen. My son was in a Med-Evac helicopter when he was 3 weeks old because they thought he might have a mal-rotation in his intestines. It was the scariest night and day of my life, but it turns out he was fine, he just needed to fight a virus. I will never forget leaving the NICU at Children’s and thinking how lucky I was. Most families that are there don't leave, or at least not for good.
My wife and I spent six months pouring our souls and life savings into a home renovation, only to stay in it for 7 nights before it was wrecked in a 100-year flood. It sounds really bad, and again, it was really scary and stressful. My wife was 6 months pregnant, but kind of like leaving the hospital, we had flood insurance and were made whole in the end. Lots of people lost everything in that flood.
I guess the worst tragedy I have been impacted by was when one of my former college roommates died 3 years ago. He had struggled with substance abuse for a while, but had just become a father and seemed to have everything on the right track. Then I got a call from one of my other buddies that brought me to tears in the middle of IKEA. Young people pass away all the time, way before they should, I had just never experienced it. So for the first funeral I have ever attended to be for a college swim buddy who wasn't even 30 yet, it shook me a bit. It also taught me that we have to live every day the best we can. It made me better about keeping in touch with the people close to me, and really trying to get the most out of everything life has to offer. He made a huge impact on my life, and maybe an even greater one when he left us way too soon.