Q:

What does "life plays tricks on him" mean?

What does this statement mean?

Life plays tricks on him.

Is it similar to

He has a twisted fate.

A:

Both of the statements are idioms and have similar meanings.
Life plays tricks on him means that he often has to deal with unexpected events that seem to force him to make changes to his plans.  
In the second idiom twisted generally means cruel or perverse.  The first idiom would seem like an understatement for someone with a twisted fate.  
The first would infer the frequently encounters obstacles but can be dealt with like the loss of a job.  The second infers something much worse.

