Putin is a KGB officer who rose to the highest position in his country, then formed a position above that for himself. I’d say he is very calculating.
These are both very smart, ruthless, calculating men. I think the biggest difference is where in the timeline each is currently at, their ultimate goals, and the time they feel they have left to achieve that. Other key differences I would say are cultural, reflecting more on what their goals are and their method of achieving them.