I'd say one of the problems in your sentence is the fact that the structures you've used before and after the word "or" are not parallel (i.e. not the same). The use of "whether playing" means "whether he is playing".
There are other problems as well, however. For example, can you really have "extensive experience with the knowledge of poker"? (I'd say no.)
For an example of the way you're trying to use "whether", look here (under "whether...or"):
http://dictionary.cambridge.org/define.asp?key=90189&dict=CALD
"Someone's got to tell her, whether it's you or me."