Always start out with Dorans Shield instead of a brawlers glove and a health pot and a mana pot because the armor in the beginning makes you able to sustain in lane longer which is great for Gangplank. After the getting the Dorans Shield, I prefer the Berserkers Greaves over the Ionian Boots because CDR in the beginning is not needed for Gangplank no matter what people say; more attack speed, more crits, more kills. Manamune, is a no-no to get on a Gangplank, the spamming, is not that great with Gangplank, it takes a while to stack and overall, having the "extra" mana for spamming, is not needed because mid to late game, you have enough mana and should be able to conserve the way you want. So instead of rushing tear and what not, go Zeal and then Executioners Calling in that order because Zeal for attack and movement speed, and Executioners for life steal and double passive equals OP status. After getting your Executioners, start building your Infinity Edge like normal because that is the main item you need for him. Once you have your IE, complete your Phantom Dancer for more crits and after that, build your Trinity Force, because the extra movement speed is amazing and all you have to do in team fight is pop Raise Morale and then hit someone with a crit and they die. What most people disagree with is the, Tiamat. The Tiamat is your friend because it procs off of your Parley and if the enemy team is low and close together, you can probably drop their own team with one shot. Towards late game, you going to want to upgrade that Executioners for more and more life steal and damage so upgrade it to a Bloodthirster and you should have around 400 attack damage and if you can't get it soon, then just stick with your Executioners because it will sustain the whole game.

I always start off with Parley first for the early damage is really good for getting that last shot on minions and champs because your passive applies onto them which is really good. Once lvl 2, get Scurvy right after no matter what because it rids of CC and heals. Get Scurvy again at lvl 3 for more healing and then get Raise Morale,