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Not Updated For Current Season
The masteries shown here are not yet updated for the current season, the guide author needs to set up the new masteries. As such, they will be different than the masteries you see in-game.
For items, the stats that Gangplank needs to fulfill his support damage role are: Armor Penetration, Cooldown Reduction, Chance to crit, Damage and Health (among other forms of survivability). The described item build attempts to maximize all of these things.
Stage 1 (starting items):
Goals: Farm with Smite and Parrrley. Try and stay in your lane long enough to get to Stage 2 items.
Commentary: Starting mana regen remains about the same. Health regen suffers, but you make up for it with an extra health potion. Early game crit chance is dramatically less than before, but with the right lane partner, you should still be able to grab some early kills, especially now that you have so much armor penetration to start. Melee is quite viable in a lot of level 1-3 situations. Look for when your lane opponents overextend themselves. Most players won't expect Melee + Parrrley + Ghost to drop them before they return to the safety of their tower. Health potions will be your primary source of HP regen for the remainder of the laning phase. Buy more when needed.
Goals: Use Smite and grab Golem buff. Begin using Parrrley non-stop to farm and harass your lane opponents. Establish lane control. Be mindful of other lanes that could use a Cannon Barrage to gank or push down a tower, or to thwart enemy ganks in other lanes.
Commentary: With the improved damage scaling on Parrrley, I have decided it is most prudent to rush an Infinity Edge. Missing out on chance to crit is okay so long as you can make Parrrley non-crit for a fair amount of damage early on. You can upgrade the Meki Pendant to a Chalice of Harmony, but I find I don't need it that much early. Later in the game, if I have 500 gold laying around, I will upgrade the to a Chalice for a little extra magic resist. Finishing an Infinity Edge fast (before 20 minutes if you can) is the way to go. The faster you get it, the more likely you are to snowball on the enemy.
Goals: Team battles and pushes will start taking place, make sure to Parrrley the enemy DPS and use Raise Morale when appropriate. Use Cannon Barrage once the enemy is committed to the fight. Continue to grab golem buff if possible.
Commentary: Finish that Infinity Edge asap to take advantage of the buffed damage scaling. Even though you are no longer doing magic damage with parrrley, you still cannot neglect the awesome potential of cannon barrage, and hence should get Sorcerer's Shoes in anticipation of upcoming team battles. Other boots provide marginal benefit to Gangplank at this point in the game. It works well to grab it around the time that your Cannon Barrage hits level 2. Build up your chance to crit by grabbing another Cloak of Agility.
* OR *
Goals: The enemy's natural armor should be increasing now beyond your current penetration capabilities. Build a Last Whisper to keep up with their armor growth. Get your crit chance up more by grabbing another Cloak of Agility or Zeal. The Cloak of Agility gives you more chance to crit, the Zeal gives you some movespeed and a number of Stage 5 build options. Try to end the game now with your team, if possible. Your tremendous mid-game advantage will start wearing off. A well-executed Cannon Barrage could help win your team the game here. Winning one big team battle usually results in the enemy losing one or more inhibitors.
Commentary: Basically this part of the game is about grabbing more damage, armor pen, and chance to crit. This is the core build. Most games should end here. If the game doesn't end you will need to make some end-game decisions. Be prepared for Stage 5. HP and survivability will be crucial in this next stage.
Stage 5 (when the game just won't end):
* OR *
Goals: Games can be decided upon how well you can use Cannon Barrage; Don't let your team down. Your mid-game advantage should be wearing off by now, and you will need a serious HP boost to keep doing damage. Gangplank will need HP and a targeted slow at this point because of his new dependence on doing melee damage in addition to parrrley. Sell the Chalice and grab a Phage. At this point you have several options, depending on how you built in Stage 4:
* OR *
+ /or/ /or/ /or/
Commentary: In general, you want: Core build + Frozen Mallet/Trinity Force + Phantom Dancer/Other Defense Items. Trinity Force can actually give you a viable damage boost. In my opinion, since the nerf to Sheen, an early Sheen is no longer viable, but getting a Trinity Force in a late game situation could greatly improve your odds of winning. It's obviously all quite situational at that point. Stage 4 will determine how you build in Stage 5.