I'm trying to think of games that can be pokemon related, involve strategy, and can have gambles.

OK... Try this one then...
Pokemon Roullete. Modfied to include strategy.
Player A and Player B both agree to this in thread, and a number of points is chosen. (This number will be X)
Player A PMs the dealer with one of the following: Bulbasaur - Chikorita - Treecko - Turtwig.
Player A then distributes X points amongst those 4 pokemon.
Plyaer B then distributes X points amongst 2 of those 4 pokemon.
The dealer reveals which pokemon Player A selected. If both players put points on that pokemon, then all points are distributed in a ratio as close as possible to the ratio of points on that pokemon. If only one player put points on that pokemon, that player receives all the points. If neither player put points on that pokemon, the points are split equally between the players.
The process is repeated with Player A and Player B switching places.

As an example.
Blade and Rossy agree to play, each using 20 points. I will be dealer. Blade PMs me Treecko, and posts as follows:
Bulbasaur: 6
Chikorita: 8
Treecko: 6
Turtwig: 0
Rossy then decides that Blade clearly chose either Chikorita, but to be safe, he'll also bet on Treecko, since it's one of the ones that Blade put 6 on. He puts 12 points on Chikorita and 8 points on Treecko.
I reveal that Blade actually selected Treecko. Since the points on Treecko were 8 from rossy and 6 from Blade, the points are distributed 11 to rossy, and 9 to blade.

If, instead, Rossy put the 8 points on Bulbasaur (and the 12 points on Chikorita), Blade would have received all 20 points.