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If I gain the Tavern Brawler feat, and use it with a rope as an improvised weapon, can I initiate a Grapple at 20+ feet away (depending on the length of rope)

When you hit a creature with an unarmed strike or improvised weapon on your turn, you can use a bonus action to attempt to grapple the target.

So as an action I attack by whipping the rope out, presumably doing 1d4 damage + strength (up to the DM). Then as a bonus action I initiate the grapple by tugging the rope and having it wind around the opponent.

I envision this as a lasso, but I suppose a grappling hook would work too.

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Even if your DM rules that the rope can hit from 20 feet, your reach is still 5 feet and grappling uses a free hand.

Grapple says:

Using at least one free hand, you try to seize the target by making a grapple check instead of an attack roll: a Strength (Athletics) check contested by the target's Strength (Athletics) or Dexterity (Acrobatics) check (the target chooses the ability to use).

Grapple requires a free hand, and the arm connecting that free hand is almost certainly not 20 feet long. I’m pretty sure the best we can do is the bugbear playable race with 10 foot reach on melee attacks.

Further, there is already an item that does exactly what you are trying to do here, the net:

A Large or smaller creature hit by a net is restrained until it is freed. (Range 5/15).

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  • \$\begingroup\$ So the phrasing to me seems to indicate you are grappling with either the unnamed strike or the improvised weapon that initiated the grapple. And using the specific over generic rule, that would indicate to me that the weapon in this case is what is doing the grappling. Not the free hand. \$\endgroup\$
    – Sam Lacrumb
    Jul 20, 2020 at 3:26
  • \$\begingroup\$ I don’t see that at all in the phrasing, where are you getting that? How are you making a grapple with, say, a bottle of wine used as an improvised club? \$\endgroup\$
    – Thomas Markov
    Jul 20, 2020 at 3:27
  • \$\begingroup\$ I can in fact do that, thanks to martial arts. I can also grapple you with a pen. Watch any Jackie Chan movie and he grapples with all sorts of things. But in this case specifically .. a lasso... dont you think it would make sense? As for the wording: When you hit a creature with an imp weapon on your turn, you can initiate a grapple.. implying with the weapon you struck with... Otherwise you could just initiate the grapple as an action anyway, The feat wouldn't do anything extra. \$\endgroup\$
    – Sam Lacrumb
    Jul 20, 2020 at 3:31
  • \$\begingroup\$ A grapple requires a free hand and nothing in the feat description says otherwise. \$\endgroup\$
    – Thomas Markov
    Jul 20, 2020 at 3:32
  • \$\begingroup\$ Also, you wouldn’t be able to initiate the grapple since you used your action to weapon attack, not grapple. The feat gives you grapple as a bonus action, something that normally takes a full action. \$\endgroup\$
    – Thomas Markov
    Jul 20, 2020 at 3:34

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