"I just said, 'What are you always doing over there with that?'" recalled Bailey, who spent three seasons with the A's. "And he kind of explained that he started a charity for pediatric cancer research and awareness. I said, 'Is there anything I can do to help?'"
Four years later and Breslow's Strike 3 Foundation, with the help of Bailey, now a board member, had raised $740,000 toward childhood cancer research. And that's not counting Monday's event.
Most of the Red Sox's squad of 25 was in attendance at Alden Castle in Brookline on Monday night for Sip Happens, which invited participants to taste wine, enjoy fine dining, mingle with Red Sox players and place bids on auction items ranging from vacation packages to a Les Paul guitar signed by the entire team.
With an all-volunteer staff supporting Breslow's Strike 3 Foundation, which includes Breslow's fiancee, Kelly Shaffer, and a generous donation made from a variety of local vendors, it allows for a heavy portion of proceeds to be donated to charitable causes.
Even after the Sox had just returned from Detroit, where they lost three of four to the Tigers, and the record-setting heat was clearly getting the best of the air-conditioning in the old, brick-covered building, Sox players filtered in to support Breslow on one of their rare days off.
"We have a pretty close team, so I have a lot of guys here to support," said Dustin Pedroia, who abandoned the suit in the evening heat in favor a cream-colored button-down shirt. "Bres with his cause, it's been fun. We're just having a good time. We're all enjoying the day off and doing it together."
Breslow started the foundation in part because his older sister, Leslie, was diagnosed with thyroid cancer when Craig was 11 years old. Leslie has been cancer-free for more than 20 years, but Craig has continued to support the cause.
"My life was affected pretty drastically when my sister was diagnosed with cancer," the Red Sox lefty said. "I was young. I didn't totally understand what that meant. It was a pretty scary time for me and the rest of my family."
Breslow learned quickly that starting a charity would be a lot of work. He routinely puts in 20 hours or more each week toward running it.
"Here's a guy that wakes up in the morning and does his work, and then goes to work," Bailey said. "Every waking moment is Strike 3. Then he goes to the field and there's a break from that. He enjoys it because then it takes his mind away from the game as well. It really speaks to the passion he has about the cause."
Jon Lester, who was diagnosed with cancer when he was 21, was treated and is now cancer free, runs his own charity, NVRQT (Never Quit).
"Me and Bres have a lot of similar aspirations as far as raising money for cancer awareness and different things," Lester said. "So it's a good thing for us to come out and support him and be involved in this. Especially him being a home-grown guy [from New Haven, Conn.], there's a lot of good things he's done up here the last couple of years."