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This is a bit challenging to phrase, so I'll use an example.

A human wizard with the Tavern Brawler feat gets fed up with a unruly Gnome and snaps off a heavy gate post to stab him with. The DM rules that the post is similar enough to a pike to use its damage dice. Is the Wizard proficient in this improvised Pike?

A related question queries whether or not an improvised weapon deemed similar enough to an actual weapon is still improvised - the consensus was that it was.

If that's the case, the Tavern Brawler feat states:

You are proficient with improvised weapons.

If this too is the case, does this create a loophole of sorts where a character can wield an improvised variant of a weapon they otherwise couldn't use proficiently?

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    \$\begingroup\$ I can't help but notice it's the wizard that took the tavern brawler feat \$\endgroup\$ – MrSpudtastic Oct 31 '19 at 18:55
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    \$\begingroup\$ Personally, I think a Bladesinger Wizard who sings to the gatepost she uses as an improvised pike is a freakin' hilarious concept. \$\endgroup\$ – Rykara Oct 31 '19 at 19:07
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    \$\begingroup\$ "proficiency" on it's own does not mean a lot. The Wizard will be Proficient with Improvised Weapons (as the TB Feat says so). Are you asking if they can be considered Proficient with Pikes, if the DM rules that the gate-post is similar enough to a Pike? \$\endgroup\$ – Black Spike Oct 31 '19 at 21:18
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The key to this answer is in the rule about treating improvised weapons as normal weapons:

At the GM’s option, a character proficient with a weapon can use a similar object as if it were that weapon and use his or her proficiency bonus.

If a character proficient with a weapon can do something and you aren't proficient with a weapon, you can't do that thing. The rule just doesn't apply at all.

In other words, if you have an improvised weapon and aren't proficient with a similar weapon, you don't have the option to treat it as that weapon. Your gatepost just is what it is.

So yes, a wizard with Tavern Brawler can wield a random gate post more proficiently than an actual pike.

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    \$\begingroup\$ "So yes, a wizard with Tavern Brawler can wield a random gate post more proficiently than an actual pike." More proficiently (may add their proficiency Bonus), but for less damage (uses Improvised Weapon damage, rather than pike damage) \$\endgroup\$ – Black Spike Oct 31 '19 at 21:37
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    \$\begingroup\$ I don't think I follow this logic - your quote covers the proficiency aspect, but it does not address this aspect of the rule: "Often, an Improvised Weapon is similar to an actual weapon and can be treated as such." 'Treated as such' to me indicates that you take on its conditions, such as 2-handed, heavy, and damage dice. Your quoted rule only covers proficiency. \$\endgroup\$ – Nicbobo Nov 1 '19 at 0:41
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    \$\begingroup\$ @BlackSpike An improvised weapon considered "similar to an actual weapon" doesn't do that actual weapon's damage? PHB p. 148 says only "an object that bears no resemblance to a weapon deals 1d4 damage". \$\endgroup\$ – aschepler Nov 1 '19 at 14:58
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    \$\begingroup\$ @aschepler you are right. I had missed the "no resemblance" bit, and thought all Improvised Weapons did 1d4. If the DM decides that a Gate Post is a bit like a Pike, then it does Pike damage. You can add your Proficiency Bonus to the Attack Roll if you are Proficient in either Improvised Weapons or Pikes. \$\endgroup\$ – Black Spike Nov 1 '19 at 15:30
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    \$\begingroup\$ It is NOT "basically the real weapon". Look, suppose you grab a pitchfork. First, the DM looks it and says "That's close enough to a trident" and applies the trident stats to it. Then, if you're proficient with tridents, you might be able to count as proficient when you attack with the pitchfork. If you AREN'T proficient with tridents, that option doesn't exist, so it's still an improvised weapon for the purpose of proficiency. At that point Tavern Brawler stands up and says, "Aha! I make you are now proficient with that!" \$\endgroup\$ – Darth Pseudonym Nov 3 '19 at 15:16
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Yes

If someone with the Tavern Brawler is wielding an Improvised Weapon that a GM may allow to be used proficiently with some weapon proficiency per this rule:

Often, an improvised weapon is similar to an actual weapon and can be treated as such. For example, a table leg is akin to a club. At the GM’s option, a character proficient with a weapon can use a similar object as if it were that weapon and use his or her proficiency bonus.

... it is still an improvised weapon, and therefore someone with the Tavern Brawler feat would be proficient.

That being said, it is up to the GM entirely whether or not the improvised weapon can be used as another weapon, meaning the GM is perfectly within their right to say that the object wielded by someone who is not proficient is no longer treated like that weapon. This would mean in the hands of a fighter, the gate post may serve as a pike, but the tavern brawler just uses it as a regular improvised weapon.

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