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Quick update - 6/08/82
I also demoted a few items from "strong choices" to the new "honorable mentions" category.
I've been weirdly reluctant to give Mobility Boots a try, and... they are amazing. CDR is a really strong stat on Leona generally, but Mobility Boots are amazing, and you don't really need AS boots with Blade of the Ruined King self-synergizing enough as it is (and with AS marks helping too). Also, runes, masteries, and Spirit Visage can bring your CDR over 30% on their own, thanks to the Spirit Visage buffs a while back.
The main reason for this overhaul is a new item rework: Blade of the Ruined King. It singlehandedly turns Leona into an almost-reasonable duelist. No other item in the game does this, so I would expect more nerfs in the future. But for now, it is actually a viable item to rush on Jungleona. Throw in a pair of Berserker's Greaves and you're doing real DPS, you can solo dragon, and you have a 15% health nuke. It's insanity really.
However, a more conventional hard tank approach can work very well if you're confident that your carries can carry for you. In this case, Sunfire Aegis by itself clears out camps and minion waves about as fast as you need them to. The downside is that your DPS slumps while you wait for the item to finish building, making mid-game jungle clears very slow. :(
One solution is Sunfire Aegis, but it has to be completely finished before any DPS is gained. This is a very awkward solution which will lead to a mid-game income slump unless you get some lucky ganks in.
The newer, smoother fix is Blade of the Ruined King, which is all that Leona could ever really need to clear in a reasonable amount of time, while it also makes her DPS presence in fights noticeable, though a little behind that of most bruisers. Bilgewater Cutlass is pretty good for only getting partway there, and the active for CC might be all you truly need in many cases.
I've tested a bunch of setups in Custom, and these two seem to be the fastest. As of 06/08/13, BotRK is more effective for both clears and teamfight damage, but future nerfs could swing it back in favor of Sunfire Aegis. In any case, the convenience of Bilgewater Cutlass as a partial item is great for Jungleona in any case.
* Strong ganks
* Tons of CC
* Blade of the Ruined King gives much more damage than you're probably used to from Leona
* Sunfire Aegis option keeps clear speed reasonable without loss of tankiness
* Not gold-starved
* Much better duelist mid-to-late game than enemies may be expecting
* Slow first clears
* Blade of the Ruined King option is squishy, and overcoming that with a mid-game Giant's Belt is expensive, making it hard to ward much. It takes about three items to make the BotRK option work without blowing up instantly in teamfights.
* DPS in jungle slows down between the early game and when you finish Sunfire Aegis, if you use Sunfire Aegis as your clearing item
* Having to explain and convince to teammates that you're actually going to jungle Leona can be a pain
* Needs an ally or two in the lane to do much; often can't clean up after a lane wipe, making her a risky pick ( Blade of the Ruined King mitigates this issue a moderate amount)
* Generally team-dependent as always. If you get in a jungle fight, you need your team to chip in to get a win for the team. Don't get caught.
* Gold can get spread thin mid-to-late game if you have to pick up slack when your support doesn't ward. (Every jungler should buy a ward or two each recall anyway, but bad supports can force you to do even more)
(Not an item, but relevant to itemization.)
First off, AS marks are just as essential to Jungleona as they have ever been. The strong synergy with Hunter's Machete makes Jungleona's first clear bearable, and they scale into the late game better than other options.
Sunfire Aegis clears camps very quickly with the 20% bonus from Spirit Stone. However, Sunfire Aegis takes a while to build and does not add any damage before completion. You will have to gank more in the mid-game to compensate for the damage lag if you rush Sunfire.
This is pretty mandatory. You can pick up the red buff at the end of your first clear, but scout around first. The best upgrade by far is Spirit of the Ancient Golem, mostly because it builds out of Giant's Belt and is gold-efficient stats-wise for the next 600 gold.
This item is the only item in the game which can singlehandedly make Leona into a somewhat decent duelist. It's OP and will probably get nerfed soon, but for now it's viable as a rushed item on Jungleona. Consider Bilgewater Cutlass + Spirit of the Ancient Golem mid-game to avoid getting too squishy, or rush the whole blade if you think you can get away with the squishiness. In either case, this is the ONLY non-tank item you need to build. ( Zeal as a sixth item for move speed is also reasonable)
These are incredible. If you just want to play bodyguard and spam peel stuns, then Ionian Boots of Lucidity are good, but a mid-game Spirit Visage and CDR glyphs can get your CDR over 30% on your own. With move5 boots, you can be a lot more aggressive, and 5 seconds isn't actually that long of a time to wait for the passive to kick in. They just aren't any good if you get caught flat-footed, so play smart and avoid skillshots.
- It also might be tempting to build Sightstone, but both Blade of the Ruined King and Sunfire Aegis are difficult to rush if you take such a detour. I'd consider picking up an occasional ward instead.
- Other items are important too, but these are more typical Leona items rather than ones that specifically address how she is going to jungle. The rest of her build consists of big tank items experienced Leona players might build on her anyway, given enough farm. (Well, in longer games anyway; support Leona might end the game with Aegis, boots, and Sightstone half the time...)