Biggest Sports Betting Wins — Monday, April 20, 2026
5 notable wins | Total payouts: $333,500 | Total taxes: $92,544
5-leg parlay on Kraken vs Canucks — $500 turned into $254,000
Source: RedditOBBBA Note: If this bettor had $253,500 in losses elsewhere, they'd still owe $6,084 in 'phantom income' tax under 2026 OBBBA rules.
8-leg SGP on Main Event — $200 turned into $42,000
Source: RedditOBBBA Note: If this bettor had $41,800 in losses elsewhere, they'd still owe $1,003 in 'phantom income' tax under 2026 OBBBA rules.
10-leg parlay on Lakers vs Celtics — $20 turned into $22,480
Source: RedditOBBBA Note: If this bettor had $22,460 in losses elsewhere, they'd still owe $539 in 'phantom income' tax under 2026 OBBBA rules.
futures bet on Championship Game — $50 turned into $15,000
Source: X/TwitterOBBBA Note: If this bettor had $14,950 in losses elsewhere, they'd still owe $359 in 'phantom income' tax under 2026 OBBBA rules.
moneyline bet on Cubs vs Cardinals — $10 turned into $20
Source: X/Twitter