But by the time Josh's flight landed in San Francisco at 10:30 a.m. PT, the Rockies outfielder had officially entered the event and determined that it would be his older brother who would serve as his pitcher.
"This was totally unexpected, but it was kind of like a dream come true," said Josh, who was officially hired as an assistant baseball coach at Arizona State University on Tuesday. "You do this together in your backyard and then the high school field and then the college field, and now you get to do it on a Major League field. Unbelievable."
Although the recruiting trail he'd navigated over the past month had prevented him from throwing, Josh, who is 30 years old, still had little trouble hitting the sweet spot of his 27-year-old brother's bat in the early going. While hitting five of the first nine pitches he saw over the outfield wall, the Rockies outfielder attained a total that earned him a spot in the semifinal round.
"I haven't thrown any balls at all and then, the next thing you know, you have to throw it right over the plate," Josh said. "I didn't want to take away from his chances of winning. I did OK. He did OK. We had fun."
After hitting eight homers in the semifinals, Holliday had to wait to see if the respectable total would be enough to earn him a spot in the finals. Eventual winner Vladimir Guerrero's late semifinal flurry gave him nine homers, enough to end what was still a memorable family event.
"I wish I could have gone further," Matt said. "But it was awesome, a lot of fun."
What was supposed to be a two-day trip to enjoy his brother's second All-Star selection turned into one that allowed Josh to gain first-hand knowledge of the Major League experience. Within hours after getting to town, he found himself wearing his personalized National League jersey, wearing a new set of spikes and gaining his own All-Star experience with the younger brother that he helped mold into an All-Star.
Throughout the event, the two boys were performing in front of a proud set of parents, who when they awoke, certainly didn't realize how special Monday would prove to be.
"It was an amazing opportunity," Josh said.