The Scot left a 10-foot putt worth $85,000 on the high side of the eighth hole and was feeling its effects afterwards. Even though he's made millions in his long career, Montgomerie said the money was on his mind as he stood over the putt.
'That's why I probably missed it,' he said. 'If I'd not thought of the money, I would have knocked it in.'
Canadian Stephen Ames was the only player other than Daly to win a skin on the first day. His birdie on the third hole was worth $15,000. Retief Goosen and Geoff Ogilvy were also shut out.
The final six holes of the day were carried over, which means $315,000 is up for grabs Tuesday.
When the players return to the 10th tee, they'll be playing that hole for $125,000.
'I put a bad stroke on (the putt) really,' Montgomerie said. 'I missed it but never mind. It means there's more in the pot for the 10th hole.'
When the holes start carrying over, things get a little more serious at this lighthearted event.
The first nine holes were easygoing. Montgomerie and Ames each had a vocal group of followers on Monday and Daly did his best to entertain everyone else.
He drove the 390-yard second hole before making a birdie to take his two skins. He also drove it over the green on the 341-yard fifth hole.
'He can practically drive every green, which is what he was doing today,' Ames said. 'The idea of this format is to entertain everybody out there.
'Giving him the opportunity of driving the greens is what it's all about.'
The five players combined for 16 birdies, especially refreshing for the players coming off the tough conditions they faced at the U.S. Open in Oakmont, Pa., over the weekend.
'Perfect,' Ogilvy said. 'Even the practice rounds are brutal in the U.S. Open. It's nice to have some fun and actually make some birdies.'