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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.
Trundle is designed to be anti-tank but with this build it adds the ability to not be nuked while you eat tanks, the nukes won't be able to destroy you.
The first item bought is the regrowth pendent, as this is step one towards Warmongs. This will allow you to lane for longer if you are laneing or regain the much needed health while waiting for the jungle respawn. After that You will want to start looking towards the late game against any tanks. If there are more then 2 nuke magic users such as Ryze, Annie, and Lux: go with Mercury's Treads instead of Ninja Tabi, as it will give you the dodge bonus to avoid some up-close shots while you eat tanks and anything else that gets in your way.
Next is the Force of Nature:
Force of Nature is a great item as it gives you a huge amount of health regain and movement speed. Oh! It also gives you 76 Magic Resistance! This will be huge when you go to eat Shen when Ryze pops out of the bushes and tries to blast you, but oh wait! You are almost unaffected by it because you have 3k health and so much resistance that it bounces harmlessly to the floor. Then you eat Shen, who tries to jump away, but pillar cuts him off, slows him down, and you feast some more, Ryze trys to help him more with his pitiful normal attack, but lets face it, it sucks.
The Sunfire Cape is the tank essential because tanks do not do much damage naturally. To help a tank become a solo push up the top lane while everyone is in a stand off mid, you need the 40 damage/second. The extra life and armor are also nice, but the extra 40 damage aura is what you actually need. BONUS: While you are eating - stealing armor, damage, resistances, from your victim, he will be taking the damage too, and even if you are just close enough, but not able to hit, you will still be damaging that champion. So Shen shoots at you, you bite him, he blades you, which does nothing as it is magic damage, and tries to jump away, you bit him, pillar him. Ryze jumps close enough to you to strike, you eat Shen again, and as your attention is on Shen, Ryze is taking damage, which you then turn to Ryze and eat him too.
This item gives health and Mana to you. The mana isn't what we are after, but it helps. With the extra health, you can now take on Shen and Ryze. Eat Shen, steal all of his good attributes, then eat Ryze, who's nuke will probably taken by Banshee's Veil. After he runs, you chase, once again, Pillar, and have a Ryze dessert with your Shen Dinner.
This gives the ending health and damage. The damage isn't big, but the slowing of targets is. This late in the game you will be in team fights and you will be the anchor of it all. Who ever you hit first and slow will be who the team kills first. Make sure you choose the biggest baddy first. The Morekiesers, Shens, Cho'Goths, and other tanks are a must. You will make them soft and with the tank missing, the squishies will fall fast.