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Swain, Grand General of Noxus
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Swain's first ability is Decrepify. Swain sets his Raven to cripple his enemy, dealing damage over time and slowing the target. Note that Swain is free to move around as the source of the damage is technically the Raven. Also note that the spell is on a tether and can be broken by simply walking out of range. I take Decrepify at level 3 and leave it there.
Swain's second ability is Nevermove. Swain marks target area and after a short delay, enemies in the area are damaged and rooted in place for two seconds. Because of the long cool-down i take Nevermove at level 2 and max it second.
Swain's third ability is Torment. Swain afflicts his target, dealing initial impact damage, damage over time, and causing them to take 8% more damage from Swain's attacks and abilities over the next few seconds. I take Torment at level 1 and max it right away.
Swain's ultimate is Ravenous Flock. Swain transforms, taking the form of a Raven. This ability consumes mana as long as it's active. As long as the ability is active, three Ravens strike out at up to three enemies, prioritizing champions, dealing damage and healing swain for half the damage dealt. As with all ultimates, i take a point in Ravenous Flock at level 6, 11, and 16.
From here, adapt your build. If your dealing with Magic Damage, then pick up a Chalice of Harmony for it's magic resist and mana regen; if your against Cool-Down based Magic Damage, then you may want to skip the Chalice for an early Negatron Cloak and, if you can complete it before the 15 minute mark, upgrade it to Abyssal Mask. If your enemy is a Physical Damage carry, then pick up a Chain Vest.
After, upgrade to Sorcerer's Shoes and finish Rod of Ages (remember to get ROA at or around the 15 minute mark, this will allow a few extra minutes for any necessary changes to your build without taking too much away from ROA's passive).
From here, pick up a Zhonya's Hourglass as the Laning Phase should be ending and the active from Hourglass allows Swain to survive most fights (pay special attention to yourself during the fight as you want to save your Hourglass' active for when/if the enemy starts focusing you). If the Laning Phase is not over or if the game is progressing rather slowly pick up either Chalice of Harmony or Abyssal Mask, whichever you didn't pick up earlier.
Once you have Zhonya's Hourglass, upgrade or pick up Athene's Unholy Grail as this item is essential for Swain, almost more-so than any other item in the build; If you haven't picked up/needed Abyssal Mask, do so now or before Athene's as Swain does need to be relatively close to his targets and the Magic Resist de-buff combined with his Torment allows for extremely high dps (Player's Choice, do NOT pass up on either of these items at this point in the game).
Lastly, finish your build with Rabadon's Deathcap. However, this is the least important item in the build, so don't think twice about replacing it with different items. My top recommendations are an early Moonflair Spellblade, against heavy Crowd-Control teams/champs such as Amumu and Nautilus, and Guardian Angel, for games where you're carrying your team outright and have begun Snowballing out of control/you're the most likely focus for the enemy team.
Swain's natural tankiness and high damage allows for an aggressive early game. Use Torment to harass your opponent, pushing them away from the minions and denying them gold. Upon reaching level 2, look to keep your opponent away by leading them with Nevermove, and at level 3 keep your eye out for potential kills. If you can catch your opponent close enough with Nevermove, open on them with Torment and Decrepify, followed by a couple of auto attacks. If your having trouble rooting enemies with Nevermove, Decrepify's slow makes it easier. Remember, establish your role as a bully and make sure to last hit as many minions as possible to keep your mana up.
Also, buy plenty of Wards and be wary of enemy ganks. Swain's ability to over-bear on his opponents may make for a quick and relatively easy push, but it also makes him a prime target for ganks from enemy champions. If you catch a gank early enough, swing wide of it and attempt to halt it with Nevermove. Failing the root, slow the enemy with Decrepify. Don't worry about fighting back, just get to the safety of the turret and signal for help.
Remember that Swain is not a TRUE Tank and, as such, should not be the first one into the team fights. Once the fight has started, push your way in with Ravenous Flock. Don't worry about using all of your abilities. Tactical use of Nevermove and Decrepify allowa Swain to play somewhat of a Warden, making sure that weak enemies are unable to flee the inevitable end.