Betting $100 Every Day for a Year: Day 259 (NFL Week 2 Picks) Iain MacMillan breaks down how he's betting $100 on NFL Week 2 action on Sunday. 4:18 Now Playing Paused Ad Playing Betting $100 Every Day for a Year: Day 252 (NFL Week 1 Picks) 5:47 Now Playing Paused Ad Playing Betting $100 Every Day for a Year: Day 294 (NFL Week 7 Picks) 4:31 Now Playing Paused Ad Playing Betting $100 Every Day for a Year: Day 266 (NFL Week 3 Picks) 4:17 Now Playing Paused Ad Playing Betting $100 Every Day for a Year: Day 295 (Sports Equinox Bets) 4:05 Now Playing Paused Ad Playing Betting $100 Every Day for a Year: Day 301 (NFL Week 8 Picks) 5:00 Now Playing Paused Ad Playing Betting $100 Every Day for a Year: Day 248 (NFL Picks for Opening Night) 4:19 Now Playing Paused Ad Playing Pro Football Today's Best Bets for NFL Week 2: Bet on Cleveland? 5:02 Now Playing Paused Ad Playing Betting $100 Every Day for a Year: Day 292 (CFB + NHL Picks for Oct. 23) 2:41 Now Playing Paused Ad Playing Betting $100 Every Day for a Year: Day 288 (Monday Night Football Picks) 3:41 Now Playing Paused Ad Playing Betting $100 Every Day for a Year: Day 258 (College Football Picks for Sept. 19) 4:25 Now Playing Paused Ad Playing Betting $100 Every Day for a Year: Day 259 (NFL Week 2 Picks) Sports Illustrated Sun, Sep 20, 2026 Iain MacMillan breaks down how he's betting $100 on NFL Week 2 action on Sunday. Betting $100 Every Day for a Year: Day 259 (NFL Week 2 Picks) Iain MacMillan breaks down how he's betting $100 on NFL Week 2 action on Sunday. 4:18 Now Playing Paused Ad Playing Betting $100 Every Day for a Year: Day 252 (NFL Week 1 Picks) 5:47 Now Playing Paused Ad Playing Betting $100 Every Day for a Year: Day 294 (NFL Week 7 Picks) 4:31 Now Playing Paused Ad Playing Betting $100 Every Day for a Year: Day 266 (NFL Week 3 Picks) 4:17 Now Playing Paused Ad Playing Betting $100 Every Day for a Year: Day 295 (Sports Equinox Bets) 4:05 Now Playing Paused Ad Playing Betting $100 Every Day for a Year: Day 301 (NFL Week 8 Picks) 5:00 Now Playing Paused Ad Playing Betting $100 Every Day for a Year: Day 248 (NFL Picks for Opening Night) 4:19 Now Playing Paused Ad Playing Pro Football Today's Best Bets for NFL Week 2: Bet on Cleveland? 5:02 Now Playing Paused Ad Playing Betting $100 Every Day for a Year: Day 292 (CFB + NHL Picks for Oct. 23) 2:41 Now Playing Paused Ad Playing Betting $100 Every Day for a Year: Day 288 (Monday Night Football Picks) 3:41 Now Playing Paused Ad Playing Betting $100 Every Day for a Year: Day 258 (College Football Picks for Sept. 19) 4:25 Now Playing Paused Ad Playing
