Now fielding the pop fly on artificial turf as a participant in the Urban Youth Academy's Coaches Clinic at Wesley Barrow Stadium, Montgomery turned to a legend.
University of New Orleans coach Ron Maestri -- the first man to lead a Louisiana team to the College World Series -- instructed Montgomery to anticipate the hop before it happens.
Montgomery followed suit, fielding the next ball cleanly before taking his cuts in the batting cage.
Maestri and a group of his Privateer players joined coaches and players from LSU, Grambling and Southern as instructors for the two-hour clinic, which was followed by a college and career fair attended by five universities and two companies.
A baseball player since he was 9 years old, Montgomery joked that his high school team is virtually unheard of, but clinics and events at the Urban Youth Academy refine his fundamentals and helps his chances of landing a coveted spot on a college baseball roster.
"It's nice to bring their wisdom to us," Montgomery said. "You learn from them, and they're a big help in my baseball career."
It's a luxury Karr head baseball coach Donnie Russell only wishes he had as he ascended the baseball ranks in the mid 1990s.
A former Grambling catcher, Russell preached consistency and an easygoing nature to the handful of his players who attended the clinic, as he sensed most were anxious at the prospect of playing in front of Maestri and his counterparts.
"It was kind of tough for us, but we're making sure these kids get seen and get noticed," Russell said. "They were nervous that college coaches were going to be out there, but I told them, 'Do what you do every day. Go out there and have fun.'"
Opened in November 2012, the New Orleans Urban Youth Academy already has 1,150 registered players and averages 60 kids training and working at the field per day, according to New Orleans director Eddie Davis.
Davis, who grew up with Russell and played All-Star baseball with him, laughed that the South is more known for its football prowess, but asserted the fervent interest in baseball was the impetus for the Academy's opening, before adding that clinics and fairs like Saturday's only serve to preach that it's about more than just baseball.
That idea was on display Saturday as a student broadcast team served as the public-address announcers for the clinic, and that same group ran all the technology in the press box. Davis also said he sees kids more interested in umpiring and field maintenance, and -- most importantly -- a college education.
"The quicker we can have these kids find out what they enjoy and what they love, the better off they're going to be," Davis said.
Andrea Palmer, who watched her two sons, Aaron and Andreas, participate in the clinic, marveled at the all-in-one afternoon that promised to impart both baseball and life lessons to her boys.
A native of San Francisco, Palmer said the initial move to New Orleans was a shock after her upbringing in the baseball-crazy Bay Area, but the Urban Youth Academy has provided her family more than she could have envisioned.
"They take young kids and develop them and work with them," Palmer said. "Teaching them the basics, the foundation. This is an opportunity that's unheard of, and something we have to take advantage of."
"I just can't believe they're doing all this here," she added. "I wish more people were here to take advantage of it."
The kids and parents who do utilize the Academy are at an advantage, according to MLB vice president of youth and facility development Darrell Miller, who said the league knew it had to pour more resources into the talent-rich New Orleans region.
Miller was excited at the college presence at both the clinic and fair, heeding to the mantra he's set forth for all Urban Youth Academies.
"When you pick up a baseball, you pick up a book," Miller said. "That's our new mantra. These guys understand that they go hand in hand."
For Palmer, that's all she wanted to hear. With a 27-year-old daughter already graduated from college, Palmer understands how difficult it can be to make that journey.
And if it took all night, she was determined to show Aaron and Andreas what the schools present had to offer.
"Look, this could go on all night, and I wouldn't leave this spot," Palmer said. "I just can't believe they're doing all this here."