I understand what you are saying, but what you are referring to is withholding on one paycheck/period. The reason your withholding is typically higher on a bonus when you have a normal job is because you are already in a higher marginal tax bracket (your other income has already put you there). When you have withholding from an employer your compensation and withholdings are reported to you at the end of the year on a W2. You then use that to file your taxes and the amount you had withheld that is over your tax liability is what is refunded to you.
When you are a pro skier with contest winnings it is not the same as being paid on a W2 from an employer. It is essentially the same as being paid as an independent contractor, you have zero amount withheld and then at the end of year your earnings are reported on a 1099. That is then filed on a schedule C and, if you haven't made estimated payments to the IRS (which you have to do if your income is over a certain amount), you pay the tax you owe at year-end on your tax return.
Point is there is zero amount withheld on contest winnings. Yes, I imagine Dale has some income so he isn't starting in a zero percent tax bracket with the $100K, but what I am really trying to say is that he will not be paying his marginal rate (the highest tax bracket you fall in) on all $100K.
Additionally if that $100K is paid to Dale, then redistributed to the other guys at 4bi9, the amount restributed is deductable to Dale as compensation expense to his film crew (then reported as income to who it is redistributed to). Thus further reducing his taxable income and liability. You can use this technique to distribute it amongst everyone to stay in the lowest marginal bracket, further reducing your effective tax rate (tax liability / income). It could even be paid to 4bi9, if it is registered as an LLC or corporation, and depending an how much money 4bi9 earns could be taxed very very little.
Bottom line, if he wins, the government will not be keeping $40K. If they are someone dropped the ball.