Not quite, maybe your taking the wrong connotation with the word gambling.
For instance against Chelsea Neto did not expect WJ to win a Header and flick it onso did not make a run beyond and 'Gamble' on the flick on.
Its not following in on a Shot Gambling on a spill from Keeper. It was evident a few timesagainst Palace, Moutinho's corner, no one Gambled onthe ball missing everyone and bouncing middle of the goal 5 yards out.
Best example was Andy Gray at Wembley gambled (his words) on Needham and Shilton screwing up.
No manager will base his team on Gambling, what he will do in a team meeting is showing highlights and telling players to expect the ball to reach them.