K so here's my thinking:
Say Ernest wins the first one, after winning that first one he decides to throw in $1,000 into each subsequent draw just because. He won money, he's up, he wants to give more to charity, doesn't matter why. These are the subsequent 23 draws and his odds of winning them based on throwing in $1,000 to each, and the ones he won.
| Winnings | Total bought | Odds | |
| $30,380.00 | $60,760.00 | 1.65% | |
| $37,570.00 | $75,140.00 | 1.33% | |
| $54,410.00 | $108,820.00 | 0.92% | |
| $32,960.00 | $65,920.00 | 1.52% | |
| $5,000.00 | $10,000.00 | 10.00% | |
| $10,775.00 | $21,550.00 | 4.64% | |
| $6,070.00 | $12,140.00 | 8.24% | |
| $1,980.00 | $3,960.00 | 25.25% | |
| $31,505.00 | $63,010.00 | 1.59% | |
| $75,125.00 | $150,250.00 | 0.67% | |
| $29,020.00 | $58,040.00 | 1.72% | |
| $11,625.00 | $23,250.00 | 4.30% | Won |
| $6,420.00 | $12,840.00 | 7.79% | |
| $6,710.00 | $13,420.00 | 7.45% | |
| $5,000.00 | $10,000.00 | 10.00% | Won |
| $16,190.00 | $32,380.00 | 3.09% | |
| $5,375.00 | $10,750.00 | 9.30% | |
| $5,885.00 | $11,770.00 | 8.50% | |
| $4,955.00 | $9,910.00 | 10.09% | |
| $5,080.00 | $10,160.00 | 9.84% | |
| $7,065.00 | $14,130.00 | 7.08% | Won |
| $38,220.00 | $76,440.00 | 1.31% | |
| $4,455.00 | $8,910.00 | 11.22% | |
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Suddenly it doesn't look so impossible. Maybe still implausible, but I don't have time to re-learn statistics enough right now to figure out the odds of winning those 3 within those 23.
EDIT:
@GeorgeJETson are you able to figure out the odds of what I laid out there? I did a bit of an approximation and came up with ~11%. I can't remember how to do binomial distributions with varying odds. If that's even the way you would need to go here.
