There is no hidden meaning in the phrase "pitch and toss" found in Rudyard Kipling's poem "If."
Pitch and toss is a game which was begun in the United Kingdom. It is played all over the world.
The game (also known as Pitching Pennies, Pitchy, or Jingles) is simple. Players all face a wall with different denominations of coins. Each player takes their turn tossing their coin at the wall. The person who is able to land their coin closest to the wall (face up) wins all of the money thrown in the round. Another way to play is for all players to place a bet (put money into a pile) and then toss for the pile. The person closest to the wall with a coin face up wins the entire pot.
The use of this game in Kipling's poem refers to the fact that one must be able to play without having a feeling of loss to be successful.
If you can make one heap of all your winnings
And risk it on one turn of pitch-and-toss,
And lose, and start again at your beginnings
And never breath a word about your loss;
According to eNotes summary on stanza three, the game illustrates the fact that a person must regard wins and losses as not being something permanent in life.
The advice provided in stanza three fits in with the theme of the poem, which is to advise a young man of the qualities he has to strive for and acquire in order to become a morally upright and respected human being.
"Pitch and toss" alludes to a game of chance—as the two previous posts indicate. What the speaker suggests is that true moral value and courage lies in the ability to risk everything that has been gained and not complain once it is lost but to rebuild from scratch and regain what has been lost. Such an act suggests a paradox, for the speaker essentially states that any young man worth his salt will not cry over spilled milk. He will instead be happy regardless of the outcome of his actions and have the courage and determination to recreate what has been lost.
The mere act of risking everything to gain a greater advantage was, in the type of paternalistic society in which the poem is set, seen as a remarkable display of manliness. A man was supposed to be morally upright and loyal to his family, his king, and his country and give everything as proof of his commitment. Such a man did not make excuses for his failures but had the vigor, drive, and bravery to recreate and face whatever trials and tribulations life may throw at him.
In essence then "pitch and toss" is a phrase which symbolizes the vagaries of life. The term alludes to the uncertainty that one faces—nothing is guaranteed. The expectation as expressed in the poem is that if one should wish to be judged capable as a man, one should be able to deal with whatever destiny brings into one's path, and one should not be afraid of taking risks no matter what the perceived outcome might be.
I beleive that it is a game on with you bet on money.