Biggest Sports Betting Wins — Monday, May 25, 2026
5 notable wins | Total payouts: $410,000 | Total taxes: $110,698
$410,000
Total Payouts
$110,698
Total Taxes
27.0%
Avg Tax Rate
🥇
NHL11-Leg Parlay
$380,000
from $500 wager
11-leg parlay on Rangers vs Bruins — $500 turned into $380,000
Source: RedditTax Breakdown (Pennsylvania)
Net Profit
$379,500
Federal Tax (24%)
-$91,080
State Tax
-$11,651
Take-Home
$276,769
OBBBA Note: If this bettor had $379,500 in losses elsewhere, they'd still owe $9,108 in 'phantom income' tax under 2026 OBBBA rules.
🥈
March Madness5-Leg Parlay
$22,000
from $50 wager
5-leg parlay on First Round Upset — $50 turned into $22,000
Source: X/TwitterTax Breakdown (Arizona)
Net Profit
$21,950
Federal Tax (24%)
-$5,268
State Tax
-$549
Take-Home
$16,133
OBBBA Note: If this bettor had $21,950 in losses elsewhere, they'd still owe $527 in 'phantom income' tax under 2026 OBBBA rules.
🥉
NBA4-Leg SGP
$5,400
from $20 wager
4-leg SGP on Warriors vs Nuggets — $20 turned into $5,400
Source: RedditTax Breakdown (Illinois)
Net Profit
$5,380
Federal Tax (24%)
-$1,291
State Tax
-$266
Take-Home
$3,823
OBBBA Note: If this bettor had $5,380 in losses elsewhere, they'd still owe $129 in 'phantom income' tax under 2026 OBBBA rules.
#4
MLBFutures
$2,200
from $10 wager
futures bet on Astros vs Rangers — $10 turned into $2,200
Source: X/TwitterTax Breakdown (Florida)
Net Profit
$2,190
Federal Tax (24%)
-$526
State Tax (no tax)
$0
Take-Home
$1,664
#5
UFCStraight Bet
$400
from $200 wager
moneyline bet on Co-Main Event — $200 turned into $400
Source: RedditTax Breakdown (California)
Net Profit
$200
Federal Tax (24%)
-$48
State Tax
-$19
Take-Home
$133