PEORIA, Ariz. – Baseball has a way of writing a family’s story.
This one begins with James Passilla, a right-handed-hitting shortstop who started his professional career in the Cincinnati Reds' system in Moultrie, Ga., in 1956. Stints in New York, New Mexico, Washington, Florida, Illinois and South Carolina were to come during his Minor League tenure before he hung up his cleats and transitioned into his second career working for Disney in Florida.
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Passilla had a daughter, Connie, who then had a baseball-loving son in her own right. Which is where Carson Montgomery enters the picture. A native of Windermere, Florida, just 10 miles from Disney World, the 6-foot-3 hurler has long been an intriguing prospect. He was the No. 34 prospect in the 2020 Draft class and hailed as the top prep arm in the perpetually stacked Florida ranks, but complications from the Covid-19 pandemic and his strong commitment to Florida State led to him going undrafted in the shortened five-round format.
Notable high school names from that Draft class who've already made their mark in the big leagues include Pete Crow-Armstrong, Masyn Winn and Colt Keith.
Also a part of that class – but also choosing instead to go onto college – was Enrique Bradfield Jr., now the Orioles’ No. 4 prospect. Montgomery and Bradfield met on the Florida prep scene as amateurs and then played together both in the PDP League and on the USA collegiate national team in 2022. They’ve been reunited in the Fall League with Peoria as Bradfield has had a center-field seat to watch the Padres right-hander.
“He's always had the ability to get on the mound and pump some good fuel,” said Bradfield. “Obviously, he’s continuing to just hone his craft. His secondaries have gotten a lot better. He fills up the zone. He's making guys swing-and-miss. He's putting the ball in our hands behind him and we're able to take care of that. So he's doing exactly what he needs to do.”
Coming out of high school, Montgomery was able to routinely pump his heater into the upper 90s. He looked destined to be a frontline starter for the Seminoles, but he battled his command mightily once he arrived on campus. The strikeout stuff was there over parts of three seasons (10.1 K/9), but so were the walks (5.9 BB/9). When the Padres came calling in the 11th round of the 2023 Draft, Montgomery – now the No. 211 Draft prospect in his class – inked a deal.
“I loved it there,” Montgomery said of his time in Tallahassee. “I don't regret it at all, it was absolutely a great experience going to Florida State.”
Pitching in the ACC also set the stage for Montgomery’s transition to pro ball. San Diego started his first campaign in the Single-A California League in 2024 and watched him strike out 10 of the first 30 batters he faced. But there was one problem: his right elbow was barking. After more than two months of deliberation and trying to avoid it, Montgomery underwent Tommy John surgery, ending his '24 and '25 campaigns. Or so he thought.
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Montgomery didn’t make it back in time to pitch during the '25 Minor League regular season, but Padres prospects have a unique advantage: if tabbed to participate in the Fall League, they get to continue their rehab at the club’s complex in Peoria while also getting to face some premier prospect competition. It’s a win-win opportunity for those looking to make up for lost time.
Through his first four outings for the Javelinas, Montgomery turned in a 1.74 ERA and has seen the velocity on his sinking fastball rebound into the mid 90s.
“Every day is different coming back from Tommy John,” said Montgomery. “Some days, I'm completely dialed in. Some days, I don't feel like I have it. But just trying to get more consistent with the way I'm feeling is kind of a goal.”
Montgomery has certainly had time to refine, revamp and tinker, going 18 months between in-game reps. He has been primarily a sinker/slider pitcher against righties in the AFL, while also sprinkling in his changeup against lefties. But more than results or sequencing or pitch shapes, it's been the journey to get back to this spot that he’s cherished the most.
“What other time in your career do you get a full year to kind of work in the weight room and just not have to worry about competition for once?” said Montgomery. “Kind of just work on getting yourself better – diet, weight room, getting bigger, faster, stronger. I think that's the positive side of things if you do it right, and I feel like I did a pretty good job and our training staff did a pretty good job.”
When a given Draft concludes, there’s often talk about picks who could be viewed as “steals.” Injuries always complicate things, but the Padres – who've overhauled their Top 30 Prospects list the past few seasons chasing Major League roster improvements – can hang their hat on getting a former top Draft prospect into their system.
“He definitely looks a lot better than he did when he was younger,” said Bradfield. “That's a compliment to his work ethic, just the maturity of growing up and refining your stuff as you go along this journey.”
Said Montgomery: “I feel like composure is [the big] thing. It definitely came with more innings and more experience. I feel like as a young guy, [you] kind of ride the highs and lows a little more when things are going well and feeling good, and then when things don't go so well, sometimes you get down in the dumps. But learning to not worry about results as much and more about the process and if you feel good – that's really what matters at the end of the day.”