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Not Updated For Current Season
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This is the build I've found myself using when I've been experimenting with Trundle. It takes some time to become a true threat, but you definitely can become a key part of your team. He is an excellent ganker with all his movement control and Agony.
Trundle's skills are very situational. They have many uses in different situations because of each having multiple utilities to it, so I'll go trough some of the ways I've found to effectively use them. Keep in mind your passive let's you gain health from everything that dies near you, so you can hug a turret instead of going b. Just don't die.
Rabid Bite - Your main attack. Every 4 seconds(before CDR) you deal bonus damage and apply any on-hit effects like Trinity Force. It is instant while also reseting your attack timer, so if you fail a last hit you can pop it to get a second chance. This should be spammed pretty much, as it also can give you a slight charge.
Contamination - A game changer really. At rank 5 it is 40% movement speed, 60% attack speed, and 40% reduced crowd control effects. It only lasts 8 seconds though. Pop this in a team fight and feel free to mess someone's day up, or use it to chase. Also a great initiator should you build a more tanky Trundle as you take 40% reduced CCs.
Pillar of Filth - Possibly the most fun ability. At rank 5 it decreases all enemies around it's movement speed by 40%. It is also impassable terrain. This is an amazing ability to chaser because of the slow. Great isolator if you can seal off the rest of the team and create a 5v1 or 5v2. Also, can stop a chase and save a team mate, by itself. I've also found you can use it for scouting. Afraid the team is about to gank you? Pillar it. If they're there, they're slowed and cant catch you. If they're not, you can push safely.
Agony - The most situational ability of them all. You siphon a small amount of health, 250 at rank 3, but steal Armor and Magic Resist. Maxing at 25%, then an additional 25% over 6 seconds. In other words, this can turn any tank into a squishy. I like squishies. I'd suggest saving this ability for focusing a tank, or a carry that's built a lot of resistances.
I decided to build Trundle more like a Fighter/Carry. Similar to how you may see an Irelia.
Trinity force is a major item. It solves a lot of your problems, and improves your best aspects. It increases your speed, which when combined with Contamination, makes you give Teemo a run for his money. It gives you mana allowing you to essentially spam his abilities. Health for your tanky side. An on-hit effect for Rabid Bite.
Mercury Treads I put there as I've found it to be the safest bet for me usually. You are somewhat tanky so having a tank item or 2 isn't a bad idea, by far. I'd say adjust this accordingly. Merc treads for general teams, Ninja Tabi for physical heavy teams.
Stark's Fervor and Infinity Edge I have listed as my general transition. However, if your team is doing well, I'd say grab Infinity Edge first. It increases your damage by an incredible amount. Then grab Stark's. However, I find in most games Starks Fervor coming first benefits my team more, and this is a team game.
As for the last 2 items, I very rarely make it this far. I'd say about 10-20% of the time. I have Last whisper and Black Cleaver for damage and Armor Penetration since all of your damage is physical. However, feel free to adjust these as needed. Magic Heavy team? Hexdrinker or Banshee's Veil are good choices. Physical team? Randuin's Omen is a good choice, or Frozen Mallet.
I'm not going to lie, runes have been the hardest part of this. As I find him to be an anti tank, I like the Armor Penetration runes to reduces people's armor to almost 0 around me. The Dodge and MR runes are there so that you can survive more throughout the game. If anyone has any better suggestions please help improve this guide.
-Tips and Tricks-
Trundle is effectively an anti-tank, keep that in mind. He can negate their resistances(and steal them), and he heals from their health. In other words, either way they build he benefits.
Pillar of Filth can be used for scouting as well as slowing people.
By around level 10-11, if your team does not have a jungler, you can solo the dragon easily. After killing him, you also gain 200+ health.
Trundle can jungle very effectively, but I have yet to try it as I usually play with another jungler.
Although Rabid Bite will not hit a turret, it can still boost your damage. Also, it reduces enemy damage by half of the amount you gain.