Fresh off caddieing in last week’s Bermuda Championship, ESPN+ and Golf Channel announcer Doug Smith joins The Loop to tell us about the experience. He’s also played Tony Finau for cash recently (only getting one a side!), so Smith tells us what it’s like to play with Finau. Plus, he has some hilarious stories from the 2000 PGA Championship at Valhalla when he almost took out Jim Furyk in the parking lot and got quite a death stare from Tiger Woods. Plus, the boys celebrate their first Victory Cigar moment in a long time (courtesy of Cuvana) after hitting a college-football total and going a combined 7-2 last week in the NFL.As always, check GolfDigest.com for our full array of gambling content, including picks from our anonymous caddie, Pat Mayo of DraftKings/Mayo Media Network; Rick Gehman of RickRunGood.com; Brandon Gdula of numberFire/FanDuel; and Lee Alldrick of FanShareSports.