As soon as at least one second of the first round passes in a professional Boxing match that Paul has with one of these people, their option will resolve YES.

When Jake Paul announces his retirement from boxing, all of the other answers will resolve NO. If he dies before this happens, all of the other answers will also resolve NO.

I'm aware that people sometimes come out of retirement and have more fights afterwards, but for the purposes of this market we will take Paul at his word if he announces his retirement.

Any boxing match must be a professional bout in order to count - an exhibition will not count for the purposes of this market. A fight under MMA rules would not count for the purposes of this market.