Riddle Quest: Journey Through Time

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1.
I was a legendary Yankee known for my record-breaking home runs and was one of the first athletes to obtain a New York Life policy. Who am I?
2.
After my presidency, I served on New York Life’s board of directors. Who am I?
3.
Before founding a competing insurance company, I worked at New York Life. Who am I?
4.
Before I emerged as the renowned New York Life, I bore a different name, whispered in the echoes of history. What was my birth name, or how was I referred to in those bygone days?
5.
Answer: Nautilus