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The Rakaning, the Sickening
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Rakan is a controller type of champion with high mobility and crowd control, with a high skill ceiling. Rakan has probably, tied with bard, one of the best support kits, great mobility and the ability to quickly roam around the map and catch people with his w, Grand Entrance to open up an opportunity for the laner. After getting a few items, he can really turn a teamfight around with his ultimate, The Quickness, and his ultimate works perfectly with any kind of AoE engage the team has to provide, for example, Dragon's Descent or Mega Inferno Bomb.
His laning phase is pretty weak, but he can deny pretty much every trade with his passive, Fey Feathers and Battle Dance. His Gleaming Quill isn't really strong in the early laning phase, because the range is poor and going up to its range will leave you in aa range of both laners.
Every engage by Rakan's team should be started by Rakan, as he has two solids engage and a good disengage.
Greater Quintessence of Ability Power
Rakan disposes of extremely high AP ratios on every skill he has so having 15 supplementary AP in lane does help with sustain and damage.
Greater Mark of Magic Penetration
Magic penetration runes synergize really well with Rakans early game damage that is purely AP.
Greater Glyph of Magic Resist
Magic resistance is a very common rune for many roles and is rather self-explanatory. You take it to avoid the poke and burst from magic damage supports and mid laners.
Greater Seal of Scaling Health
As late game is Rakan's shining moment, scaling health will help him have a bit more of health when ulting in the enemy team, and help his weak mid game.
Wanderer or Savagery
Easy choice, as you won't be hitting anything with your poor aa range and q range, so Wanderer helps a lot to roam.
Runic Affinity , Secret Stash or Assassin
Another simple choice, our jungler won't be giving out buffs to the support, or you can be sneaky with an Ivern jungler and 'accidentally' walk over the circle, but other than that, Runic Affinity is useless. The only potable and good pick would be Secret Stash for the laning phase sustain.
Merciless or Meditation
As Rakan, don't plan on doing any damage early on, so the early mana sustain from Meditation is the choice to make.
Greenfather's Gift , Bandit or Dangerous Game
Dangerous game can already be put aside. Greenfather's gift may look like a tempting offer, but it is only valuable in lane and even there, your range is really limited, so pointless to pick. The gold income from Bandit stacking up with your ancient coin will really get you to your late game spike than Greenfather's Gift .
Precision or Intelligence
Here's an interesting one, the magic penetration would be great, but the cooldown of Rakan's spells are pretty high even in the late game, so an additional 5% works really well on him.
Stormraider's Surge , Thunderlord's Decree or Windspeaker's Blessing
As we won't be bursting 30% of someones health at any point during the game, Stormraider's Surge is out of our choice pool. Thunderlord's Decree would see like a great choice, but the burst potential of Rakan is based off his ability to land a short range with a one second wind-up skillshot, so we can fallback to Windspeaker's Blessing . Windspeaker's really helps out throughout the laning phase up to the late game where he can heal all of his team with a q.
Recovery or Unyielding
As Rakan isn't meant to be a tank, recovery is the best choice here, to give a bit more sustain in lane.
Explorer , Tough Skin or Siegemaster
As we picked up some movement speed in the cunning tree, picking Explorer would stack up the roaming potential and to go drop wards.
Runic Armor or Veteran's Scars
Another easy choice, more regen from Runic Armor and strong healing, where Rakan shines with his double shield and healing.
Insight , Perseverance or Fearless
As bot lane is where the jungler's attention is the most focused, most of the times, and where the summoners are usually all burned during a skirmish, having 15% reduced timers on your summoners spells is really a plus throughout the game.
Gleaming Quill is a really good skillshot in teamfight that has a great healing potential mixed with items, but it isn't worth upgrading before maxing e-w. In lane, you can try and sneak in the bush to aa-q for a potent trade and heal, but you'll mostly be using this is lane when chased to get a healing during your disengage or on a cc'ed target.
Grand Entrance is the main engage you will use in laning phase and to combo after your ult. This spell is your main skillshot and you need to know how to properly use it. Try and center it when going in, since the wind-up takes a bit of time, one second, to trigger the knock-up. Mixed with Battle Dance, you can engage from out of vision of the enemy team by jumping onto your ally and landing your W from close range. With your ult, it is almost impossible to miss your Grand Entrance as you can gather multiple players with your charm and then knock'em all up.
Battle Dance is the best skill of Rakan, where you can really use your mobility to his best. In lane, it can be used as a double shield for your carry, re-shielding them after the three seconds delay, but also to re-position yourself after a successful or not engage on the enemy. In teamfights, you can use ardent censor at it's finest shielding your aa carries, as the healing from your shields themselves will be a lot of sustain, plus their lifesteal. Basically, your Battle Dance is your key to engage and disengage in style, while helping your team with utility.
The Quickness is Rakan's ultimate, which works as Ahri's charm mixed with Master Yi's Highlander movement speed, faster. This skill does a bit of damage by itself, 300 (+50% AP) at max rank which can do a lot of burst if you engage in the whole team. This skill can serve as a good engage for AoE teams, but also disengage as your charm slows enemies and can give enough time for your team to reposition or flee. Care though, as you can easily get bursted down if you engage recklessly.
Flash is an absolute necessary on any support, as it can serve of an engage, a kill secure or disengage, a really useful summoner for both you and your adc.
When you know your lane will be more aggressive and have more pressure on the other laners, it it better to run ignite when you know your duo can kill someone in lane. Also, it's good against high healing team like Vladimir and Warwick.
Exhaust is good against burst champions, such as Lucian, Zed or LeBlanc, so having an exhaust is really useful when fighting them.