Biggest Sports Betting Wins — Wednesday, May 27, 2026
4 notable wins | Total payouts: $136,300 | Total taxes: $39,613
$136,300
Total Payouts
$39,613
Total Taxes
29.1%
Avg Tax Rate
🥇
MLB6-Leg SGP
$106,800
from $200 wager
6-leg SGP on Dodgers vs Padres — $200 turned into $106,800
Source: X/TwitterTax Breakdown (Massachusetts)
Net Profit
$106,600
Federal Tax (24%)
-$25,584
State Tax
-$5,330
Take-Home
$75,686
OBBBA Note: If this bettor had $106,600 in losses elsewhere, they'd still owe $2,558 in 'phantom income' tax under 2026 OBBBA rules.
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NFL13-Leg Parlay
$26,960
from $20 wager
13-leg parlay on Chiefs vs Bills — $20 turned into $26,960
Source: X/TwitterTax Breakdown (VA)
Net Profit
$26,940
Federal Tax (24%)
-$6,466
State Tax
-$1,549
Take-Home
$18,925
OBBBA Note: If this bettor had $26,940 in losses elsewhere, they'd still owe $647 in 'phantom income' tax under 2026 OBBBA rules.
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NHLFutures
$2,500
from $50 wager
futures bet on Knights vs Stars — $50 turned into $2,500
Source: RedditTax Breakdown (Ohio)
Net Profit
$2,450
Federal Tax (24%)
-$588
State Tax
-$86
Take-Home
$1,776
#4
UFCStraight Bet
$40
from $10 wager
moneyline bet on Co-Main Event — $10 turned into $40
Source: RedditTax Breakdown (California)
Net Profit
$30
Federal Tax (24%)
-$7
State Tax
-$3
Take-Home
$20