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I am a rising 2L (class of 2020) looking at Biglaw. My brother stands a good chance at qualifying for the 2020 Olympics, which occur July 24-Aug 9. Would a firm ever let a new associate delay their start date or take time off right at the beginning for something like this? I would like to go and see him compete in person, but he is in the kind of event where he would not just compete once, I would go to Tokyo for a week or more within 2 months of starting at the firm.

You will likely be taking the bar exam at the end of July, 2020. In any regard, most biglaw firms don't start until mid-september at the earliest.

Yeah, if biglaw, most start dates are, at earliest, September but more often around early to late October. If mid law, probably would start around September. Wouldn't worry about this.