Greatsword Thrown weapons combo

[TheFoxWitch]

Basically I play around with unorthodox 5e builds for fun, And one of the most recent is a paladin rogue. While it'd be simple to make a duel wielder with rapiers. I thought it'd be more interesting flavor-wise to make a greatsword wielder who utilizes daggers to use sneak attack once a round. My current thought process is this.
5th level paladin extra attack
Rogue eh at least one.
Thrown weapons fighting style (Draw and throw dagger as part of attack action)

1st round of combat: free object interaction draw greatsword, attack action draw and throw dagger apply sneak attack, second attack swing with greatsword.

since the dagger is never truly "Held" could you still hold onto the greatsword which requires 2 hands?

Let me know what you all think.

[JonBeowulf]

Thrown dagger damage is pretty meh until your sneak attack die becomes interesting and you still need to have one of the conditions that trigger sneak attack.

As far as the interaction... I don't think it's RAW and it's probably not RAI, but I'd have no problem with you temporarily holding the greatsword while you toss a dagger and then wielding it to smack someone. You get the correct amount of attack rolls and the ranged attack is weaker than the melee. Seems fair.

[Gurgeh]

The interaction is absolutely fine RAW and RAI. Two-handed weapons do not require two hands to hold, they require two hands to wield. You only need to have both hands on your greatsword when you are making an attack with it; it's perfectly fine to just hold it in one hand and throw a dagger with your other hand.

Thrown fighting style gives the damage a respectable bump, turning a dagger into a longsword equivalent (and a javelin or handaxe into a glaive equivalent, though they're not compatible with Sneak Attack); the only issue is that as a multiclassed character your sneak attack dice will only be a little dash of extra hurt, rather than a big, impactful pile the way they are for a single-classed rogue.

There is a bit of an issue with your proposed order of actions, though, since your thrown weapon attacks are ranged attacks and will be made at Disadvantage if there's an enemy within 5 feet. If you successfully drop your target with the greatsword then that's fine, but you'll otherwise need to choose: throw at disadvantage, back away and potentially eat an opportunity attack, or attack again at melee range (either with the greatsword or with the dagger if the sneak attack dice are plentiful enough to outweigh the greatsword's higher base damage).

You might want to consider a reach weapon for these reasons; the damage will be lower, but you won't need to force yourself into melee range just to hit harder.

The final issue is that the official Thrown Weapon fighting style from TCoE is exclusive to the Fighter class: the Paladin can only use the UA version. This is doubly difficult since not only will many tables not allow UA, it's also weaker than the TCoE version (only +1 damage rather than +2).

You can get around this with the Fighting Initiate feat or by taking another multiclass dip into Fighter (either of which will let you apply your Paladin fighting style to something else, so there's at least a consolation prize).

[Tanarii]

Unless your DM house rules that switching how many hands you have on a weapon requires an object interaction, that works fine.

[Greywander]

Yes, it works, but as mentioned, the Thrown Weapon fighting style is only available to fighters (edit: and rangers). Personally, I would be fine allowing a player to take it as a paladin style.

You can also use darts instead of daggers, which should work just as well but are cheaper and lighter than daggers, so you can carry more of them. Do still keep a dagger handy, though, in case you need to Sneak Attack from melee. Technically, you can still draw the weapon as part of the attack, even if you aren't throwing it. You can then use your object interaction to sheathe the dagger so you can attack with the greatsword.