Tryndamere is universally acknowledged by trashy players as being the most broken character in the game. He was the first character I ever bought, and I had never seen him in game... I just thought he looked cool to play. Very quickly I realised his potential as an assassin and a pusher with a modicum of feeding. Unfortunately for our pal Trynd, his early game kind of sucks ***, which became painfully apparent when I was asked to mid one game. He's too easy to harass in lane and has no harassment of his own, without committing to a fight. So one day I decided to try jungling, figuring that that would solve my problem of going 1-7-2 before going 20-1-8. It did. I've now gotten fairly used to it, and very rarely do I get my ******y *** kicked. Tryndamere is the best jungler in the game, I'd say, because of his built-in heals, and the potential for getting firstblood at level 3 or 4. At level 6 or 7 (depending on the gold situation) you can start soloing dragon, and as long as your team isn't ******ed, winning the game should be easy.

To recap, Jungle Trynd is based on some simple premises.
-Being harassed in lane when there's nothing you can do about it is hella gay
-Getting firstblood is pretty cool
-Soloing dragon gives your team a massive gold advantage early on
-You're TOTALLY UNPREDICTABLE. You can hit up their jungle for buffs whenever you want. You can gank anyone on the map. If they're afraid of you, they'll play too cautiously. If they aren't afraid of you, they'll die.

I wrote this guide after going 16-0-4 and causing the other team to surrender at 25 or so. The glaring hole in most Trynd builds is the early and mid game, and I figured that if my Jungle build went 16-0-4, other players might be able to get some good ideas for a dominant early game.


Let's begin!

Towards the end of the game, you probably want to sell Wriggles, and you might want to sell your boots. Here are some post-sale alternative builds to use at your discretion.

IN GENERAL:
Phantom Dancer, Phantom Dancer, Beserker's Greaves, Infinity Edge, Bloodthirster, Bloodthirster is an extremely solid build. Excellent movespeed, damage, lifesteal, crit, everything you need on Trynd.

MOVEMENT SPEED IS FOR *******, I NEED TO WRECK ****:
Phantom Dancer, Phantom Dancer, Infinity Edge, Bloodthirster, Bloodthirster, Madred's Bloodrazer. Alternatively, you can sub out Madred's for another Bloodthirster, but Madred's is nice for its armour-busting 4% damage and improved attack speed.

I WANT TO SELL MY BOOTS BUT I STILL WANT TO RUN FAST TO JUKE/BACKDOOR
Phantom Dancer, Phantom Dancer, Infinity Edge, Bloodthirster, Bloodthirster, Youmuu's Ghostblade Very solid. The extra move/attack speed from Youmuu's is great when you know how to pop it.

I WANT TO RUN A MARATHON BAREFOOT LIKE AN ETHIOPIAN OLYMPIAN
Phantom Dancer, Phantom Dancer, Phantom Dancer, Infinity Edge, Bloodthirster, Bloodthirster Very viable because of the insane attack speed you're going to get, and the Phantom Dancer covers for your missing boots in the movement speed department. Not entirely, but you'll still be faster than most.

NOBODY TOOK STARK'S AND I'M KEEPING MY BOOTS BECAUSE I'M ENDORSED BY ADIDAS AND I'M TRYND SO I CAN'T WEAR ONE OF THEIR SHIRTS
Phantom Dancer, Stark's Fervor, Beserker's Greaves, Infinity Edge, Bloodthirster, Bloodthirster This is one of the most overlooked Trynd builds. Stark's Fervor is an awesome item because of the increased attack speed, lifesteal and armour penetrating qualities. If there are one or two more AD carries on your team and you need a boost for teamfights, Stark's is a MUST TAKE. If your Soraka is an *******, Stark's is MUST TAKE. Great item.

THEIR ENTIRE TEAM BUILT THORNMAIL, WHAT THE **** DO I DO
Phantom Dancer, Youmuu's Ghostblade, Black Cleaver, Infinity Edge, Bloodthirster, Bloodthirster Pop Youmuu's and Ghost to run like a normal human being.

I MISS TAKING EXHAUST
Phantom Dancer, Phantom Dancer, Beserker's Greaves, Infinity Edge, Bloodthirster, Hextech Gunblade

Buy a Vampiric Scepter. Run to small Golems. Camp out in the bush so you don't get ganked there (it's happened to me once). At 1:40, Smite one of them and engage in combat. Pop your Q once they die. With any utility points, you should be leveled. Put a point into spin.

Run towards wolves, popping your 'empty' Q as soon as it's cooled down (thanks to the new Fury system and bloodlust rework, you can now use bloodlust without any fury, for a significant heal early on). Spin them. Kill the big one first, but really it doesn't matter.

Go to wraiths. Smite the big one, spin the small ones.

There's a bit of time before golems respawn, so I recommend hitting up one of the lanes for a gank. If you haven't gotten firstblood, don't be discouraged, golems should have respawned.

Wash, rinse, repeat. Keep doing this until you're level 6 or 7ish. Once you hit 1150, you have the option of going back to base and picking up Wriggles. Sometimes I wait until I hit 2070 or so, so I can get Greaves as well.

Solo Dragon. Rejoice as your team collectively gets 1000 gold.

Red buff doesn't really speed up your jungling at all, so I don't get it until I have Wriggles already.

Remember to hit blue buff as early as you can. You can safely do it without Beserker's because chances are good the beneficiary is going to leash it for you. Be VERY careful though and stop hitting it above 600 HP. You never know when your Wriggles might activate, I've KS'd it once because of that and it didn't feel good. I suggest giving your blue buff to your top or mid, and their blue buff to your bot, if possible.

-If you see a Trynd start with Brawler's Gloves, he's probably trash. They've been a lot less good since the rework. Don't get them until you're ready to build a Zeal.
-Because of the Vampiric Scepter, there's little point in getting potions or armour. Save your gold for offensive items.
-Tempted by Avarice Blade? Don't be. It's a waste of gold, unless you're hell-bent on building Youmuu's, which you shouldn't be. It's a much more useful item on Xin or Yi these days.
AMENDMENT: Ryve correctly points out that if you manage the item cooldown, Youmuu's is arguably more useful than Phantom Dancer. Therefore,
Wriggles -> Greaves -> Avarice Blade -> IE -> Phantom Dancer -> Youmuu's -> Bloodthirster is a fully legitimate build order. It really depends on what you want to do. I like the second Phantom Dancer because I find a permanent boost to be more handy than a temporary one (not to mention I can be rather unreliable in terms of popping my Youmuu's intelligently). But really, it's personal preference.

I went for Desolation marks because I rarely purchase armour pen. Armour pen will be useful throughout the entire game.

Crit% seals because other than AS, they're the best value for money.

Attack speed glyphs are virtually the only glyphs of any use to Trynd.


Quint choice explained in comments and quoted here:
-Flat HP is great for the first three levels or so. It makes getting an early firstblood much easier, and it's more noticeable early on than a 2% crit boost, IMO.
-Furor quint is there because it's useful lategame, whereas Malice is only useful early.

Some of you might choose to swap out the Flat HP Quint. This is absolutely fine, of course. I just prefer to have it as extra insurance while vying for that firstblood.

Masteries are your pretty standard jungler ones. Just take your Attack mastery set and put a point into smite. The extra 5% experience from utility is a lot more important than you might think, and speeds up your jungling skill acquisition (with only one point, you level up on small golems, etc.).

The item build for Jungle Trynd is fairly situational, but here's what you ALWAYS want to do:
-Start with a Vampiric Scepter. Otherwise your ability to stay in jungle is decreased. Trynd with a Vampiric Scepter does not b until he has enough gold for an item you need. Simple as that.

Wriggles will give you control of buffs and Dragon right off the bat. Chances are good nobody else rushed it, it's a very solid item in general with the 18% lifesteal, damage and armour, the free ward is great (I usually ward the river across from dragon so I have extra warning to spin out if I need to), and the unique passive is absolutely awesome. Usually I don't try dragon until I have Beserker's though. You might be able to do it depending on your rune setup or whatever, but dragon's built-in slow kind of sucks unless you have SOME AS.

Whether you get a Phantom Dancer or an Infinity Edge next is totally up to you. I used to go for IE immediately but lately I've been getting Phantom Dancer instead, which I think I might prefer... the extra move speed makes not dying that much more possible. After you get the first Dancer and you've completed Infinity Edge, rush another Dancer. After that, get a Bloodthirster, sell Wriggles and get another Bloodthirster (or a Madred's, but I prefer Bloodthirsters because lifesteal essentially makes Trynd immortal) and if you're up to it, you can sell your boots and get either Phantom Dancers or another Bloodthirster.

But again, this is situational. You definitely want to start with Wriggles and Berserker's Greaves, and you definitely want a Phantom Dancer and an Infinity Edge. But if you're getting your *** CC'd to oblivion, you might want to get a Quicksilver Sash. If your team doesn't have a tank, a Frozen Mallet goes a long way towards survivability, and the passive can be very nice for hunting down and killing people. But for the most part, Bloodthirsters are your best friends. When they're maxed out (which isn't hard to do... farm a couple waves and jungle for a sec), that's +100 damage and +25% lifesteal EACH. If you have three of those mofos, that's +300 damage, +75% lifesteal. If you're critting for 1300/hit (which is a lot more believable than you might think), you're getting over 1000 HP back per hit.

GG.

Your basic priority:

Undying Rage > Bloodlust > Chicken > Winspin.

Winspin is great for juking and alright for farming, but other than that its main use is catching up to people so you can chicken them. I like to put a point into all three before pumping Bloodlust, so I can be a versatile ganker that can get in and out of situations easily. Chicken is a godsend against other AD carries or fleeing squishies.

Your basic modus operandi is to winspin into a fight and start critting **********ers. Everyone will start focusing you around this time, so hopefully you're good at hitting R. Pop Ghost, run away with your ridiculous movespeed (you have Phantom Dancers, remember?), and winspin juke the **** out of them. Kill another one or two if you can. Congratulations, you're never going to die again.

These can vary a bit. You might want to take Flash instead of Ghost, but I like Ghost because of its versatility. You can run towards a fight or away from a gank, you can sprint towards a weak tower or you can run through a minion wave to get to their fleeing Lux. Smite is pretty much a must. I've always hated the idea of Smite, but it's definitely one of the most useful summoner abilities in the game. I've thieved Baron/Dragon from the other team with it an inconceivably large number of times. I've probably won games on Baronthiefing alone.

One complaint with it is that it doesn't target Anivia's egg, and I feel like it should. Regardless, you can't go wrong with Ghost/Smite.

Pros
-With your R, good timing of your Q and some half-decent E juking skills, it's entirely possible to go an entire game while A. dealing the most damage, B. taking the most damage C. not dying once.
-You're incredibly adept at assassination. You will outrun any champ except maybe Highlander Yi. You will win every 1v1 and quite a few 1v5s with enough lifesteal.
-There is a wonderful feeling of domination when your build is complete.
-Everyone is scared of you, and they will play accordingly.

Cons
-Really vulnerable to crowd control effects
-not everyone at low ELO knows how to solo a lane, so you might lose an outer turret by jungling.
-you're a bit squishier than most Olaf builds etc., if you don't count your R.
-being a hard carry, there isn't much room for error in how you build. You're a bit wimpy unless you build properly and have a good gold pace.

Rush Wriggles.

Win game.