If I could be anyone in history I would want to be… (because..)
If I could choose anyone in history to be my friend/in my class, I would choose… (because…)
Some of our Sages interpret it [the word בְּדֹרֹתָיו] favorably: How much more so if he had lived in a generation of righteous people, he would have been even more righteous. Others interpret it derogatorily: In comparison with his generation he was righteous, but if he had been in Abraham’s generation, he would not have been considered of any importance.
בדורותיו: יש מרבותינו דורשים אותו לשבח, כל שכן שאלו היה בדור צדיקים היה צדיק יותר. ויש שדורשים אותו לגנאי, לפי דורו היה צדיק, ואלו היה בדורו של אברהם לא היה נחשב לכלום:
What advice could we give someone who is always judging themselves in comparison to others?