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Something you said made me realize I've been thinking of the Shield Master bonus shove all wrong. I've always read the feat as meaning you must first make some attack and then may use the bonus action. You are saying that you could take the bonus action first and then make the attacks - the need to take the attack action is fulfilled by simply stating that is what is happening and then may play out multiple attacks and bonus actions in any order. This really opens up my options.

I also never made the connection that a Grapple is an attack, and thus receives Advantage! OMG

Grappler builds will have a very strong Strength(Athletics), better than a normal attack for most characters. So the shield shove to prone followed by an Advantage Grapple is pretty dang optimized.

I will contest you on the opponent being prone and grappled isn't really at that much of an disadvantage. If they have multiple attacks, then simply attacking (the grappler or anyone within reach) is totally fine and will be close to the normal attacks in combat. Being prone doesn't grant Disadvantage (capital "D"). It is a disadvantage (small "d") in that options to gain Advantage become much more limited, but it doesn't explicitly make the prone attacker have to roll twice and take the worse result. It is also a disadvantage (small "d") since the grappler will have Advantage on his attacks against you. A great option is to use one attack to shove your grappler prone and then grapple them. Now neither has Advantage and is stuck prone. Or just keep attacking and dealing damage. If you are paired up with a Rogue, you are still granting the Rogue Sneak Attack damage.

Yeah man. That's the deal, you can use that bonus action anytime, before your regular action, after... whatever. So, with Shield Mastery, use that bonus action to Shove them down, get Advantage, grapple them, and then listen to the lamentations of their women as you beat the life out of them. However, even if J were to rule that you literally have to attack first in order to get that Shield Mastery bonus Shove, it's still worth going for the Prone/Grapple.

As far as the Prone status, from 'Appendix A' in the PHB, characters affected by Prone:

--The creature has disadvantage on attack rolls.
--An attack roll against the creature has advantage

Seems pretty damn clear to me! Once you're 20th level, this means that you'll be rolling 6-8 attack dice per turn, using the best of the four as part of Advantage rules, while the defender is rolling 0-8 attack dice per turn using the worst of those rolls per Disadvantage rules. More on that below.

As far as using Push to end that grapple, wellllll... you better have a good Athletics now, hadn't you? Meaning the end result is that the broken game mechanic gives a huge edge to STR builds, and in the classic game with weird monsters and shit, it gives a huge advantage because monsters aren't rocking Athletics or Acrobatics in any real way. You can find stuff online regarding how DM's find Grappler builds frustrating to deal with, because of the broken mechanic.

The bottom line is that 1 vs 1, the character with the most Athletics skill is going to either:

(1) Force their opponent into trying to escape Prone/Grappled status half the time

OR

(2) Force their Prone opponent into fighting under threat of Advantage from attack, and Disadvantage when they attack the Grappler.

Now, the real bitch is that these kinds of broken mechanics destroy diversity in games (which is why, for example, online video games take great pains to ensure balance in the game, or else, sooner or later, everyone is running around as the same character, and then the boredom and stale factor kicks in.

A great example of brokenology is the D&D fighter build. Let's compare two fighters, both level 11. One is STR 20-Athletics with Expertise, the other is DEX 20-Acrobatics with Expertise (the new DEX rules for using weapons introduced to allow diversity in the game, realistically allowing that agile characters could be as threatening as STR characters-- good move game makers, bravo there-- you got rid of the "have to be an steroid jacked monster" to be a threat, only choice for fighters. moving on, in the simplest terms, these two fighters (STR guy and DEX guy) both have respective skills at level 11 that are +13.

So, they're even. However, there is one big disparity in this case: the DEX guy can't inflict this Prone/Grapple hell, which only costs 1 attack to inflict by the Grappler. And, when DEX is Prone/Grappled, it will cost him all of his attacks to try and escape. Uh oh... suddenly the DEX guy is at a significant disadvantage. There is a game mechanic that allows STR guys to eat his attacks.

What this means, and this is one example of why the Grappler's Manual author refers to grappling as "mechanically unfair", is because it creates this massive imbalance in the game. In this case, with two prime time Fighters, one Athletics the other Acrobatics, the math works out where the Grappler will create the Prone/Grappled status on the DEX guy 50% of the time, forcing them to give up all of their attacks when it happens (literally translating to losing half of their attacks), to try and escape that Prone/Grapple hell or...

Just lie there and suck it up, accepting Disadvantage on his own attack rolls while granting the Grappler Advantage on theirs. Also a shitty play for DEX guy. Extravagantly broken, because we now have a situation that the STR guy can create 50% of the time, which will force DEX to lose all of their attacks every other round, or fighting from Prone/Grapple hell.

So, the STR gets to keep his AC to defend vs DEX guy. DEX guy... well, STR guy simply gets to ignore DEX's AC via the grapple rules, create the Prone/Grapple hell (ignoring AC the whole way), then beat DEX while he listens to the sweet music of the lamentations of the women. Which, with Athletics and Acrobatics being equal, will happen 50% of the time. You don't have to be good at math to get where that's going to lead.

These broken mechanics aren't as salient now though, because guys like Qiu only have one attack. Once we get up there in levels though, the significant advantage of the Grappler build will become far more salient. Which is why the guy that wrote the manual called grappling mechanically unfair. He knows it's a huge advantage easily exploited against certain game mechanics (monsters and non-STR build characters).

I guess what I was speaking to was the advantage portion of what you said, you can use the attack action to make the grapple check but because there is no attack roll, advantage from being prone or restrained wouldn't come into play for the grapple check.

Oh man. I must have read the appendix description for prone a half dozen times when reading up on grapple and the game mechanics of it.
Somehow I had it in my head that prone didn't impose Disadvantage and just managed to not read that bullet point. Willful blindness? That changes everything as you describe it.

I do think I have to agree with Ox on the advantage for the grapple. Prone grants advantage on attack rolls, not ability checks. Grapple attacks are made with contested ability checks. So then in that case it kindof doesnt matter if grapple or shove come first, their rolls are not influenced by one another.

Right. Athletics is a skill check, used for skills like running, swimming, climbing, heavy lifting, etc. However, for some knucklehead reason, the wizards who wrote the 5e rules decided to convert it to an attack for grappling and combat, meaning in this case grapple is an attack and no longer just an ability check. This is actually what makes the mechanic broken. Grapple is an attack... that uses an ability check, and ignores all of the combat mechanics?

Instinctively, based on the combat mechanics that do make sense, you guys are still perceiving grappling (via Atheltics) as an ability check, when in fact for the purposes of combat Athletics has been converted into an attack. Another of the real broken parts of this is that it allows Expertise to be introduced into combat mechanics, really allowing some sincere nuttery to take place in generating completely unbalanced advantages for the Grappler. CB knew to take Expertise for Athletics, and no doubt was fully aware of the devastating advantage it would give him, especially the higher level Qiu gets. At our current level the benefit of Expertise is an additional +2 to the Grapple roll. At 17th level it will mean an additional +6, since Expertise doubles your proficiency for the check. Oh shit!

At the top level, the Grappler with a 20 STR and Expertise will rock out with a Grapple attack that gets +17 to the roll. Plus 17 to the roll. Hell, CB, you should take Rogue to level 11 for Reliable Talent. With that in place (safe assumption of 20 STR by then), by 17th level any Grapple attack you make that rolls below a 10 will count as a 10, meaning every Grapple you do will result in a range of minimum 27, up to a top end roll of 37 (what!). Of course, Reliable Talent is for ability checks... and Athletics is an ability check... but in this case it's an attack during combat... and... well... you see... oh fuck. Now what?

And this is the part where you kind of think to yourself "game designers, wtf were you thinking? You didn't keep shit simple, you complicated the hell out of it."

Following the above Expertise logic, this means that any defender (with identical STR or DEX as compared to the grappler's STR) who doesn't possess Expertise in Acrobatics (to defend vs grapple) or Athletics (to defend against and use grapple against others) is at a tremendous disadvantage. And may the Gods of Dice and RNGesus smile upon them if they happened to not even take Athletics or Acrobatics as a proficiency at all, because now, even if the defender has a 20 STR or DEX, the Expertise grappler gets (+17 minus the defender's 5 for 20 STR/DEX) a total of +12 to their Grapple attack. This is a huge reason why Grapple is broken, as it completely ignores the combat mechanics of the game, allowing for unbelievably lopsided dice rolls to occur.

The above is a big part of why the Grappler's Manual author called grappling mechanically unfair. He might have been the first person to figure it out (extraordinarily doubtful in a world with 7 billion people). However, his writing is the most visible on the internet, and does a good job of revealing how grappling is screwed up (of course encouraging the the Church of Grappling to take full Advantage- ha!). And that broken mechanic is the root linked to all of the other brokenness (eating the defender's attacks as they try to escape Prone/Grapple, creating the Advantage/Disadvantage aka Prone/Grapple Hell).

Taking it another step, in any environment with natural dangers (falling heights, lava, tiger pit, etc) the Grappler just needs to grab his guy with +17 to the roll and toss him into 'Environmental Danger X'. Screw all of those turns of combat... just throw that guy into the ravine with the gators. Hmmm... how high is Fingol's place?

Everything else uses AC and Saving Throws. Maneuvers from Battle Master is an excellent example of how Grappling should have been handled. First you make contact with your attack roll vs AC, then the target resists with a STR or DEX saving throw. Easy. Attack, saving throw. Done.

As far as AC for grappling purposes, if you really want simplicity, you could just state that the AC is what it is for grappling. "Well Bob, for heavy armor we could always allow that it makes the grapple effort more difficult due to the weight or added bulk." Simple. Much simpler than throwing out the core rules just for the special snowflake that they think grapple should be, leading to combat mechanics getting lopsided and broken.

Ultimately for me, it's this basic: the rules for grapple could have been kept simple and still made sense, easily borrowing from the concept for Battle Master's Maneuvers (great examples are the Maneuvers Pushing Attack and Trip Attack). With Maneuvers the game design team knocked it out of the park... with grapple they just threw a wrench in the works.

Attack, saving throw, done. Or, if you really must: Attack, ability checks, then done. The key is to avoid creating a situation wherein the grappler gets to completely skip the AC part of the mechanic, due to all of the above reasons.

Sage advice is that Grapple is an ability check, not an attack roll: http://www.sageadvice.eu/2015/06/08/shove-grapple-attacks/

Grapple is an attack action, but the roll to determine its success is an ability check roll. Since prone applies disadvantage on specifically to attack rolls (and not more generally attack actions), grappling a prone opponent doesn't grant advantage.

Well alright then CB, I can buy that since Sage is the D&D authority (and that one really left some room for interpretation, so it's easy for me to go with Sage). Still though, the Grappler is without a doubt broken as a game mechanic, with or without that little bit of Advantage for the grapple (which can be gotten in other ways). In the end, it's far too easy for the Grappler build to create the Grapple/Prone Hell, which leads to a massive imbalance in how combat plays out (obviously I've hit those details enough).

Interestingly enough, I know that in the past the Grapple attack required a hit first to make contact (not to mention the defender got an opportunity attack first, wherein a hit would cancel the grapple), which I think connects to what you said: "grabbing hold of some guy whirling a sword around at you seems like a dangerous thing to do and maybe isn't simulated by the rules all that well."