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Jeremy E Crawford says here that (emphasis added by me):

The intent is that the druid uses the bonus in the beast's stat block for ANY proficiency the druid LACKS.

Meaning if the druid has the proficiency he can use it.

Weapon Master says I can choose four weapons to gain proficiency with.

If I choose claw, bite, sting and slam, would this allow me to add my proficiency bonus instead of the animal's to my attack rolls?

Are they weapons I can pick for the Weapon Master feat?

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  • \$\begingroup\$ @Airatome That's probably best developed within a full answer, if possible. In comments it can only be a conversation (which comments here aren't designed for). \$\endgroup\$ – SevenSidedDie Dec 24 '17 at 4:47
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No.

Weapon Master (as amended in the PHB Errata):

You gain proficiency with four weapons of your choice. Each one must be a simple or a martial weapon.

The natural attacks of beasts are not made using simple or martial weapons.

In any case, the game statistics of a druid using the Wild Shape class feature are explicitly stated to be that of the the beast plus a limited list of the game statistics of the druid's normal form. That list, as other answers spell out, doesn't include weapon proficiencies.

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    \$\begingroup\$ The bolded text is found in the errata of the PHB. \$\endgroup\$ – daze413 Dec 24 '17 at 6:40
  • \$\begingroup\$ Is it really that hard to believe a druid couldn't spend an hour a day as a lion training his natural attacks, just like a fighter does? \$\endgroup\$ – Voromir Kadien Dec 24 '17 at 17:35
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    \$\begingroup\$ @VoromirKadien I'm just telling you what the rules say. In any case, most beasts already include a proficiency bonus in their attacks (for example, a lion with a Strength bonus of +3 makes claw attacks at +5), so that really represents the level of skill you're talking about already. \$\endgroup\$ – Marq Dec 24 '17 at 18:48
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The question is moot.

When you Wild Shape into a creature, you do not retain any weapon proficiencies you normally have. From the text of Wild Shape:

You also retain all of your skill and saving throw proficiencies, in addition to gaining those of the creature. If the creature has the same proficiency as you and the bonus in its stat block is higher than yours, use the creature's bonus instead of yours.

Even if you were able to gain proficiency in natural weapons you do not have, there is no way to transfer that proficiency when you polymorph into a form with those natural weapons.

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  • \$\begingroup\$ That's not what Jeremy E Crawford the rules guru said in his tweet. And the next sentence in the Wild shape ability seems to imply you use your own bonuses if they're higher. \$\endgroup\$ – Voromir Kadien Dec 24 '17 at 16:07
  • \$\begingroup\$ @Voromir Where does Crawford say that weapon proficiencies are kept? \$\endgroup\$ – SevenSidedDie Dec 24 '17 at 16:46
  • \$\begingroup\$ see the link in the post. There are 2 tweets I only quoted the one I thought relevant \$\endgroup\$ – Voromir Kadien Dec 24 '17 at 17:05
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    \$\begingroup\$ Those tweets don't say what you appear to believe they say. When in beast form, the druid does not keep weapon proficiencies; therefore the druid does lack them and uses the beast's. \$\endgroup\$ – SevenSidedDie Dec 24 '17 at 18:52
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The stat blocks for all beasts already include their proficiency bonuses. They are already proficient with their natural weapons. Characters are also proficient with their unarmed strikes. Character races that have claws and such (tabaxi and tortles, etc.) are described that their claws are considered unarmed strikes, with which they are proficient. If a character casts Alter Self and grows claws, he is proficient with those. I would simply rule that a shapechanged Druid has his own proficiency bonus with all his attacks (in place of the animal form's proficiency).

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    \$\begingroup\$ Which is true, but the OP wants to use his own proficiency, not the beasts'. \$\endgroup\$ – Miniman Dec 25 '17 at 3:57

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