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Leona is my main champ and I jungle withe her from time to time when we have a support in a team or just feel like it :)
I usually start with Cloth Armor and a W and I clear everything at the first run with enough HP to gank after golems. Lately tried to experimenting with starting at wreiths and feel that its even better for her.
Agree that there are better junglers out there but even though Leona is not a bad pick. At least when you pick her enemy team expects a support and try to counter her, and are always suprised when they spy a smite at loading screen. :) BUT she is VERY team oriented and need a team mate to gank or finish off low hp enemy.
Well written and explained. How about alternate starting items ? I take Regrowth Pendant for a quick Philo stone and it works well... +1
What kind of clear times do you get? You'll probably need AS marks and a hard pull. It's a bit slow even with the setup I use here (well, not super-slow at 1, but it doesn't get much faster later on, either). Falling behind in exp is a risk if you can't clear the camps out in a reasonable amount of time.
Leona is just too slow, and doesn't speed up as she levels up. Her kit relies on teammates for damage. Her only strong point is her ganks - but with no health sustain (not even a shield), she has to constantly watch her health as she goes through the jungle, because if she ganks when low, she can throw the gank. Alistar is faster, can gank just as well, and probably has a better transition thanks to his ultimate. Heck, even Taric is faster than her and has equally strong ganks.
No on the long sword start...
It's strictly a farming item, and it rapidly pays for itself. Try it before you knock it.