Biggest Sports Betting Wins — Thursday, May 28, 2026
5 notable wins | Total payouts: $224,075 | Total taxes: $63,287
$224,075
Total Payouts
$63,287
Total Taxes
28.2%
Avg Tax Rate
🥇
NFL8-Leg Parlay
$194,300
from $100 wager
8-leg parlay on Ravens vs Bengals — $100 turned into $194,300
Source: RedditTax Breakdown (Michigan)
Net Profit
$194,200
Federal Tax (24%)
-$46,608
State Tax
-$8,254
Take-Home
$139,338
OBBBA Note: If this bettor had $194,200 in losses elsewhere, they'd still owe $4,661 in 'phantom income' tax under 2026 OBBBA rules.
🥈
UFC7-Leg SGP
$13,700
from $25 wager
7-leg SGP on Main Event — $25 turned into $13,700
Source: X/TwitterTax Breakdown (Massachusetts)
Net Profit
$13,675
Federal Tax (24%)
-$3,282
State Tax
-$684
Take-Home
$9,709
OBBBA Note: If this bettor had $13,675 in losses elsewhere, they'd still owe $328 in 'phantom income' tax under 2026 OBBBA rules.
🥉
MLB14-Leg Parlay
$11,050
from $10 wager
14-leg parlay on Yankees vs Red Sox — $10 turned into $11,050
Source: RedditTax Breakdown (Colorado)
Net Profit
$11,040
Federal Tax (24%)
-$2,650
State Tax
-$486
Take-Home
$7,904
OBBBA Note: If this bettor had $11,040 in losses elsewhere, they'd still owe $265 in 'phantom income' tax under 2026 OBBBA rules.
#4
NHLStraight Bet
$3,000
from $500 wager
moneyline bet on Panthers vs Maple Leafs — $500 turned into $3,000
Source: X/TwitterTax Breakdown (New York)
Net Profit
$2,500
Federal Tax (24%)
-$600
State Tax
-$171
Take-Home
$1,729
#5
March MadnessFutures
$2,025
from $15 wager
futures bet on Championship Game — $15 turned into $2,025
Source: RedditTax Breakdown (Ohio)
Net Profit
$2,010
Federal Tax (24%)
-$482
State Tax
-$70
Take-Home
$1,458