There was a subsequent tweet by JC on March 11, 2019 that says as a DM, he allows the bonus action of Shield Master to happen after you make at least one attack with the attack action, because making one attack fulfills the action’s basic definition on p192 of the PHB. If you have extra attack, you decide which of the attacks the bonus action follows.
you can take your bonus action whenever you want on your turn, unless the bonus action’s timing is specified.
(bold added by me)
This is the part of the sentence relevant to OP. In the case of both shield master and tavern brawler, the timing of the bonus action is specified. Whether or not we choose to follow Jeremy's controversial RAI regarding shield master, his clarification provides for tavern brawler to allow a bonus action grapple attempt after either attack in an extra attack situation, just as Deshiba hypothesized in the original post. My response was to Javier_Phenergan's post #9 and also to DxJxC's post #11 agreeing with Javier for what I feel is a conclusion that falls in contrast to the rule's intention.
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"Not all those who wander are lost"
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There was a subsequent tweet by JC on March 11, 2019 that says as a DM, he allows the bonus action of Shield Master to happen after you make at least one attack with the attack action, because making one attack fulfills the action’s basic definition on p192 of the PHB. If you have extra attack, you decide which of the attacks the bonus action follows.
(bold added by me)
This is the part of the sentence relevant to OP. In the case of both shield master and tavern brawler, the timing of the bonus action is specified. Whether or not we choose to follow Jeremy's controversial RAI regarding shield master, his clarification provides for tavern brawler to allow a bonus action grapple attempt after either attack in an extra attack situation, just as Deshiba hypothesized in the original post. My response was to Javier_Phenergan's post #9 and also to DxJxC's post #11 agreeing with Javier for what I feel is a conclusion that falls in contrast to the rule's intention.
"Not all those who wander are lost"