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So as far as Gankplank goes there are a lot of things that need to be said. First of all. He is squishy as all get out. I mean that. You will have long green bars that fall apart when a Shen looks at you funny. That being said. There are a lot of things he does have going for him.
Early game farm lord. - You should be able to last hit most creep per wave with that pistol. It should be remarkable how fast you make the cash money.
Early game great harass. - The pirate is not a carry and you SHOULD NOT PLAY HIM LIKE ONE. You are an anti-carry which means that if you go mid that is absolutely okay but not meant to be for anything other than shutting the other guy down early. And I mean he should die at level 6 or at least be forced to pack his bags and go home. If he doesn't. You have failed.
Damned fine bait. - Lets say that they are chasing you. Let them blow their stun, let them. I said that. Let them hit you. Then scurvy and tap your ghostblade and get the hell out of dodge. And then turn around and glock them in the face when your tank of choice or really ballsy/epic Pantheon hops ontop of their skull.
Great scaling damage - With this build in particular not only will you be getting critical hits a majority of the time but you will be doing consistent damage throughout the game. So much so that they will most often run away crying because you took a quarter of their tanks hitpoints because he's not finished with his Warmog's yet.
Late game unexpected carry slaughter - Since you are an anticarry. YOU ARE NOT TO INITIATE THE TEAM FIGHT. EVER. Unless you're dropping the HMS Awesome's balls on their head. If that's the case... STILL DO NOT RUN IN THERE. Again. Squishy as hell. However, once the tank runs in you are to climb out of the grass and two-piece their carry. Yes. That's right. You will hopefully kill them in two hits.
Map presence. - Hey look! A really huge creep-wave trying to take your top tower because they've been too busy as a team to kill it although it's 30 minutes into the game. Ka-Boom. Drop that **** and keep on being the pirate. You'll make mad duckets and experience out the wazoo. Do not however use this to stop your team from farming if they are nearby. You make plenty of money just being a pirate.
Most of all. You are never. Under any circumstance. Ever. Supposed to stack. Avarice blades. I have never found another pirate player EVER come close to the amount of success I have had by stacking those useless wall-hangers. You are a pirate and you are the damage. Therefore. Get some. The crit chance wont matter if it's only doing around 500 at level 18. Doing 1400 is much MUCH more satisfying and overall aids your team far more.
IF you do go mid. That's great. Play conservative enough to stay alive but harass them enough with your hilariously high crit chance and deal their carry a bit of something to think about. If it's someone like Tristana. Good. They don't deal enough damage early game to not warrant taking a couple of shots to hit them with the grog-soaked blade. That DOT is an extra 50 true dmg at level 1. Use it. Don't get stupid and think that you're a melee character because you're not until you get the Ghostblade but use it when you can. That glock is supposed to be rolling as often as humanly possible. Primarily to make bank off of their creep but as importantly to keep their carry on it's toes.
Other things to think about at this stage....
Is my scurvy up? If the answer is no. You have a problem. Yes. Use it to heal when it's level 2 and you're hanging out by your tower being pushed in glocking creep. DO NOT HOWEVER have it down when their jungling Warwick is CLEARLY going to be level 6 soon and for some reason their Tristana is getting ballsy... It's about awareness. If you're in a teamgame make sure that they call MIA's, if there is a jungler and you're ignoring him as a team, PAY ATTENTION to how screwed you will be if that cleanse is not up. All about keeping on your toes while you keep them on theirs.
The early item build for this is without question. There is not a better item to get. The critical chance on brawlers gloves means **** if you cannot keep the glock rolling. That's why the chalice is so important. You will never have mana problems. Ever. Feel free to spam the snot out of it once you have aquired it. Boots of mobility are what you want because they should be running from you, not the other way around, if it is the other way around you have overextended without support and deserve to wall the plank you failure. However, the pirate is forgiving in that you can scurvy out and have a chance of survival. Most certainly with the ghostblade to be tapped. You will move at lightning speeds. It will be comical. Especially when they run right into the HMS Awesome's balls that you so conveniently drop in your jogging path.
Only characters that can keep up with you are a Rammus while rolling, A Singed with ghost and insanity poison on, and a Mundo who's Ballsed out and Ghosting your way with his final on. If these are your followers... Run. And MEAN IT. Don't hang out and lure them. Just run. They mean to chase you and have the means to do it. If it's an Annie, or basically anything other than those obnoxiously fast tanks, play it cool and bait for your team.
That being said go for the brutalizer after or right before the chalice depending on how things are scaling up, meaning, have you made two kills yet unexpectedly due to them failing to hit you because you exhausted them and ripped them to shreds? Or... have they failed to kill you yet and you are still farming rather well.
However those two are key. Don't ignore them. The Brutalizer is an upgraded pickaxe with awesome strapped onto it with the price-tag of 1337 on it. Yeah. It's Leet.
Then the ghostblade which makes your auto attack a viable option if it's a squishy and you have the balls to take them in a 1 on 1. Which you should. Annie for instance. Let's say you hang out in the bushes until she blows an incinerate and an inferno and you have a guess that Tibbers is not ready to pounce on your soul. Next spell being a stun or not. Go after her. You run like the wind and start the auto attack process. Which means.
Auto Attack until...
Glock again when it's up.
Continue to Auto Attack until the Ghostblade wears off.
Wait... Are they still alive? Something went wrong. Probably Shen. F**King Shen.
Pop Scurvy during this process if things look grim between health but certainly if they blow a stun considering it's a scaling sizable heal for 380 at max level and will catch them with the "WHERE DID THAT HEALTH COME FROM?" look on their face. It's nice.
After the Ghostblade work the IE getting the cloak first, then the BF if you can afford it outright and finish up with the other 1350 between the pickaxe and the recipe. Once this is done it's leaning towards the later stages of the game. We are talking around 14-15 or so hopefully if you've farmed well and eaten towers alive with the ghostblade active. That being said other people are starting to catch up to the lololol amounts of damage that you're pumping out and in fact may try to put their pointy, firey bits inside of you in the next inevitable team fight.
Onto the mallet. I used to get a warmogs because the regen is hilarius and having a super fat pirate is funny but downright something felt wrong. It was the fact that I nearly forgot that the on-hit effects apply. Heheheh. Soak that in. Those pesky bastards always running away from that teamfight you clearly won but two of them want to play the nuthug the tower game and hold on til the team comes back to life? NERP. Shoot them with this and hey look. They can't move as well. And you caught up so you're auto-attacking them... more slow. Ohhh the doom. Taste their tasty doom.
NO ESCAPE. EVER. It's nice.
Then after wards get the Atma's others would prescribe other items and I would call them failures. They can go stack Avarice blades. Here we play the Win-beard as prophesied by Condon. Enough crit chance to laugh, and now you have Armor, a decent gut to plug around in a team fight meaning you wont be one shot usually between the Magic resistance on the chalice and the armor from the Atma's hell. You might even live. :) Especially that scurvy trick.
Enjoy yourselves and please. Do not disgrace the pirate. The pirate is a team character. You are to build to support the team and slaughter the carry. Doing otherwise is failure.