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Not Updated For Current Season
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My build is made for a Critical DPS Tryndamere that will start jungling at level 4. He starts off with a brawlers glove and 2 health pots. You shouldn't have to use both at the start unless necessary but try not to.
Once you reach level 4 you need to start jungling, so you should either go back and get health or just start jungling right away if you have the health. If you go back to heal buy an avarice blade and if you have the money start the next one. You should start right off with wolves as you will not take much damage and you can heal with your bloodlust stacks or a health pot if you still have one. (Don't waste money on anymore as you need to save up for your infinity edge.) After wolves go to the witch wraiths and if you have more then 3/4 health with no BL stacks or pots then go get the big troll monster guys. Usually if you have the proper runes you can have about 40% Crit chance while your fighting. If you still have enough health kill the small minions at red buff and make sure you don't die! Recall and buy your next avarice blade and start on your berserker greaves. Continue the jungling starting with wolves almost every time as they deal the least damage and have the least health. Once you get your ultimate (Endless Rage) you should easily be able to get the red buff and should have a crit chance of about 50-60% Crit while fighting. When possible go chase after people who are low health or hold lanes while people are recalling.
Try and stay in the jungle as much and if you are on your way to a lane kill all the jungle monsters in your way. If you get killed in a fight or just have to recall you should buy your boots and start you way onto your Infinity Edge. Don't waste your money on the Cloak of Agility or Pick Axe, as you need to save up for your BF Sword first. By the time you have this you should be cutting into lanes often and getting kills. In most games I have an average of 6/0/3 about and though you shouldn't be dying much because of your Ult, sometimes mage's get a little pesky. They are squishy and in these cases I run about a 10/2/5. Once you have your Infinity Edge you should start on your phantom dancer. Though you need to show up to team fights, try to jungle as much as possible without going back. Kill minions in lanes or monsters in jungle to get health off your stacks, but don't go back very much unless you have to.
Once you have your first Phantom Dancer you should start building a Bloodthirster starting with your Vamperic Scepter instead of the BF Sword in this case. If you are a good Trynd you should be having a decent game no matter what their team is like. You should be attending every team fight and hitting a Critical Stirke almost every attack. Your damage will very for their armor and where you are in the build but over all you should be able to do tons of damage before and especially after you hit your ult. The game from now on is pretty self explanatory. Jungle to heal as you should crit every hit, and don't be afraid to attack minions even at less then 100 health. Your lifesteal at 15% will give you tons of health as it deals off your crit chance. If deal about 500 damage crit then you should have about 80 health per hit on minions. Once you have your other Bloodthrister you will have 30% lifesteal and you can easily solo barron as you will stay from mid to high health. Because you don't need your 3rd phantom dancer at the end you should get armor or magic resist depending on the other teams composition. I prefer Wits End for magic resist and Leviathan gives me extra health, however I don't always go with it.
You need to get rid of your avarice blades and boots whenever you get enough gold to buy a major item, however, do not sell your Avarice blades just to buy a small item for phantom dancor or VS for Bloodthirster, you should only sell them when you buy an item as a whole or a major item like a BF Sword. In short you want them for the extra gold as long as possible.
You shouldn't have to much trouble killing champions in a 3v1 situation, but if you should ever meet a situation that you know you can't kill anyone in, and you will die trying, just run, don't fight. I've seen lots of bad Tryndamere's because they run in and don't kill anyone and die for it. Your passive is very nice early game but it's really not that necessary late game as your Critical chance will already be at 100%.
I don't have much else to comment on but this is a very solid build that will allow you to reck champions 1v2, solo Baron, and stay the #1 most OP champion late game that ever lived. He can turn around games that are 3v5 or 2v3 and he can single handledly wipe a whole team off the earth and out of existence. Good luck with the funnest champion to play and take the privelage of saying the famous dying words: GG