Pretty much the best choice for a starting item right now against any AD-based champ. It's sell back is one of the highest in the game so you lose 90 gold to gain an incredibly safer lane. If I don't take this it's cause im against ranged or AP.
The single most important item on Tryndamere early on. Movement speed to stick to and evade targets, attack speed to bolster his passive and take advantage of his AD steroid. It just boosts all his options for the least gold investment, get these early.
Strong choice for a later game pair of boots. You can sell the 'zerkers and switch to these later on if your team fight's not going to well based on enemy CC. Ideally we used to pick Tryndamere against teams without a ton of cc but the CC creep that league has suffered makes these boots more and more appealing every patch.
Your sustain items. Only make cutlass if you want to build a BoTRK but I personally think BT is better for carrying and team fighting. I don't make botrk on Tryndamere since I prefer to teamfight with him and BT is better in teamfights.
In season 3 these don't grant lifesteal as well as the sell-back amount has gone down so we lose more gold now - so they're even less appealing then they were before. I likely wont be making these pretty much ever.
Zeal-derivatives are really strong on Tryndamere, one day I hope PD will become a more competitive choice on Tryndamere again, but currently it seems to fall behind Shiv for less gold.
Ghostblade is basically everything that Blade of The Ruined King is, except this item feels much better than BotRK on Tryndamere. Theres no 'on hit' effect, but it has higher base AD, 20 ArPen and 15% crit which more than outweighs the ruined king passive, and the active on this has twice the duration of ruined king and only half the cooldown (45 seconds instead of ruined kings 90). During active you have the same attack speed as ruined king as well. This item isn't as good for raw tower pushing, but you should be getting good at the game and learning how to do things besides pushing towers on Tryndamere anyway nerds.
Shiv is a really good split push item, but it's also got a lot of synergy with Tryndamere's kit in general. Since the proc can critically strike, it offers quite a bit of power. The crit proc also scales with Critical Strike damage so picking up an Infinity Edge will increase the power of this item too.
Huge armor penetration but nothing else - because of this we usually build this only in response to what the enemy team is building. You may need to build this before finishing your Infinity Edge depending on what the enemy team is making, if not, it's almost always a necessity after the IE.
Infinity edge by itself has a lot of major weaknesses, but combine with statikk shiv you get around the main issue of ivesting tons of gold into damage without having armorpen which made IE rushing tradtionally bad. Since shiv deals magic damage that also scales with IE's passive, it's now much more viable to go for an early IE combined with SS.
The best lifesteal Item for Teamfighting, it grants the most damage on critical strikes and the shield and higher lifesteal percentage helps keep you alive during team fights and helps delay the use of your ultimate which extends your life span in fights.
Good for split pushing, it got its on-hit % buffed awhile ago but the lifesteal got nerfed. It's good for 1v1 duels but underwhelming in team fights where you should be targeting carries who have low HP pools thus making the % current HP passive significantly less powerful.
Less damage on crits than a bloodthirster, less lifesteal than a bloodthirster, less utility than botrk, more expensive than botrk and less expensive than a BT but not by that much. Honestly this item doesn't do anything better than BT or Botrk in my opinion and is the worst lifesteal option right now. You don't need it for split pushing and the AoE damage doesn't benefit from critical strikes, generally speaking BT is better for team fights (more LS, damage and a shield) and botrk is better for splitting (attack speed, cheaper and some utility on active).
A great endgame item for Tryndamere if the enemy team is saving hard CC's or exhausts for you, and the active now grants movespeed so you can catch up to people easier after being CC'd. That and the item now grants damage which means you dont actually have to let your DPS build suffer from making this now!
An absolutely fantastic late game addition. It's similar to the old 'Cloak and Dagger' only it provides movespeed, AD and a much larger amount of attack speed. You'll want to build this in response to either A) The enemy team is applying lots of crowd control to you in fights and you need a way to stick better or B) The enemy team is building items like Randuins and Frozen Heart in which case you'll want this for the AD/ATS to offeset that weakness. You can make this before IE depending how the game is going but you may want to wait until after last whisper since you should have your phantom dancer already.
Tryndamere with two lives is pretty scary. You can make this late game if you think it's a good choice. Sometimes the frozen mallet is better (against burst/ap damage) and sometimes the GA is better (against strong enemy AD carries).
A mediocre item in terms of survival, you pay a lot for very little defensive bonus. The only reason for this item really is the on-hit slow. Think of it like having red buff at all times. It helps a ton at kite prevention but I'm not sure this is really the ideal item for most games. A possible usefulness but outshined by other items quite often.
A lot less attractive after the attack speed has been taken off it, it could be a possible 6th item but I don't see why it's better then any of the other options. Leave it to the supports for the most case.
General preferred enchanment. Not really worth making till super late game but it's decent. The main argument is whether to get this or Furor and my argument is this. The furor provides a movespeed boost that is much stronger than this, but only if you're in melee range and abilty to get an auto-attack off. Now here's the dilema, if you're in melee range you didn't need the movespeed to begin with. Thus when you're out of melee range - the time you need that movespeed to catch up - you simply cannot because you dont have the bonus or any way of attaining it. Thus Alacrity is my choice since the boost is always there.