Biggest Sports Betting Wins — Wednesday, May 20, 2026
3 notable wins | Total payouts: $68,000 | Total taxes: $19,979
$68,000
Total Payouts
$19,979
Total Taxes
29.4%
Avg Tax Rate
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MLB4-Leg SGP
$45,000
from $200 wager
4-leg SGP on Dodgers vs Padres — $200 turned into $45,000
Source: RedditTax Breakdown (VA)
Net Profit
$44,800
Federal Tax (24%)
-$10,752
State Tax
-$2,576
Take-Home
$31,472
OBBBA Note: If this bettor had $44,800 in losses elsewhere, they'd still owe $1,075 in 'phantom income' tax under 2026 OBBBA rules.
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NFL13-Leg Parlay
$14,500
from $20 wager
13-leg parlay on Chiefs vs Bills — $20 turned into $14,500
Source: RedditTax Breakdown (Arizona)
Net Profit
$14,480
Federal Tax (24%)
-$3,475
State Tax
-$362
Take-Home
$10,643
OBBBA Note: If this bettor had $14,480 in losses elsewhere, they'd still owe $348 in 'phantom income' tax under 2026 OBBBA rules.
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NHLFutures
$8,500
from $50 wager
futures bet on Knights vs Stars — $50 turned into $8,500
Source: X/TwitterTax Breakdown (California)
Net Profit
$8,450
Federal Tax (24%)
-$2,028
State Tax
-$786
Take-Home
$5,636
OBBBA Note: If this bettor had $8,450 in losses elsewhere, they'd still owe $203 in 'phantom income' tax under 2026 OBBBA rules.