GREENWICH, CT — New York Yankees utility man Oswaldo Cabrera is a man of the people and especially the children who want to follow in his footsteps. Imagine a gym filled with kids and parents in the dead of winter in the northeast, packed into an elementary school waiting for a Major League Baseball player to walk through the door.
This was the scene at the JustinTime Baseball clinic at Whitby School in Greenwich, Connecticut, as everyone waited for Cabrera to walk in this past Sunday afternoon.
JustinTime Baseball was created by Justin Sherman to help shape a new generation of players who see baseball as a source of joy, growth, and resilience—lessons they’ll carry far beyond the field. He and Cabrera have a mutual respect for each other as they have done several events previously together, since Sherman followed him every step of the way, even through minor league rehabs.
“So we’re very picky about who we bring aboard, who we hire as a coach in our company, and who we have as a guest coach,” Sherman told Latino Sports. “Now, not only is he (Cabrera) a major leaguer, obviously, that’s also fantastic. He is a phenomenal human being with amazing empathy, energy, and just off-the-charts enthusiasm.”
“We work with a lot of players. I think he’s number one. No doubt about it with the kids.”
Justin Sherman, the founder of JustinTime Baseball, and Yankees utility man Oswaldo Cabrera delivered a memorable Sunday for the youth at Whitby School in Greenwich, Connecticut – Image Credit: Hector Beauchamp/Latino Sports
No matter the wait, the crowd reaction was even better than expected once the 26-year-old Venezuela native walked in, and upon arriving, he immediately apologized for the delay.
Cabrera was double-booked this past weekend at the JustinTime Baseball clinic and the Hall of Fame Signings at the Expo Center in Secaucus, New Jersey. He was running late to JustinTime Baseball because of this, but decided to cancel his flight to Tampa, Florida, so he could spend more time with the kids and the event.
That’s how much JustinTime Baseball means to Cabrera, and making sure each kid gets time to learn something valuable from him.
“This guy (Justin Sherman) helped me so much connect with the kids, with the community in New York, and I’m so glad that I have him in my life because this is one of the biggest key that why people love Oswaldo Cabrera so much because I got people like Justin helping me doing all these things,” Cabrera said of Sherman and JustinTime Baseball.
Sherman, the founder of JustinTime Baseball, is a former college baseball player at SUNY Purchase College. He loves giving kids a strong support system and wants his lessons to instill confidence and belief in all of the children he comes across. He also wants them to keep fighting even if they aren’t the biggest, strongest or fastest kid on the field and keep that confidence high within themselves.
“We started in a backyard six years ago during COVID,” Sherman said, revealing the origins of JustinTime Baseball. “One lesson in a backyard spaced out with masks on on a poly spot, and groups of pods became one to two to three, and then we reached out to some little leagues. One little league, 15 little leagues with 29 coaches and massive expansion geographically as well.”
JustinTime Baseball is based in Westchester County, New York, and its youth baseball and softball programs impact thousands of kids ages 3-13 every year throughout the tri-state area.
Justin Sherman and those at JustinTime Baseball believe every young player thrives when supported with the right tools, encouragement, and environment – Image Credit: JustinTime Baseball
To learn more information, you can check out their official website at JustinTime Baseball.
“I was that kid that was maybe in the middle of the pack to under the pack as far as talent,” Sherman explained. “But I had great coaches, great mentors that believed in me and truly just wanted me to be that person that gives back after. Maybe that kid’s in the middle of the pack, but give them those fundamentals to really excel forward and reach their own potential or even go further than expected.”
Several parents were thrilled for the opportunity to have their kids learn from Cabrera and spoke with Latino Sports about it.
Oswaldo Cabrera showing kids how to properly field a ground ball during their JustinTime Baseball Clinic at Whitby School in Greenwich, Connecticut this past Sunday – Image Credit: Hector Beauchamp/Latino Sports
One mother, Samantha Yustman, said “we signed up pretty fast. We do a lot of JustinTime clinics. We’ve been with Justin since he first started. And as soon as we saw that this was a clinic, we’re big Yankees fans, and I knew it would make my son’s day. So we signed him up as soon as possible.”
Yustman also mentioned that it’s a very cool experience for her son to see Cabrera on television as he tells his friends that he knows him.
“We’re extremely thankful,” Yustman added. “It really sets a great example for these little kids, and it’s something that on the way here, he was like, “This is my dream, to one day be a Yankee. So it’s a great example.”
The Venezuelan utility man expanded on why he really enjoys coming to these types of events.
“We really have fun, but also we try to take care of each and every kid that comes in here and try to put a smile and give them this beautiful moment to keep in their mind for the rest of their lives,” Cabrera said.
Additionally Cabrera answered questions from many kids and demonstrated how he practiced fielding ground balls at a young age. He also took the time to take pictures and sign autographs with everyone at the event who was interested.
Despite his hectic offseason schedule, Oswaldo Cabrera took the time to take a photo and sign an autograph for each fan who was interested no matter the age at the JustinTime Baseball Classic – Image Credit: Hector Beauchamp/Latino Sports
“I mean, my son is six going on seven, but he’s a big six-year-old,” Mike Korn, a father at the event, told Latino Sports. “And being able to be out here, some other kids that are at the same, you know, size and skill level as him is really important.”
“Oswaldo came right up to him when he walked in, and started showing him a couple of moves. So that was really impressive. And just the way that he jumped right in, slapped five with every single kid here, was wonderful.”
A remarkable person going out of his way to do this in such a crucial offseason is the Oswaldo way. While Cabrera continues rehabbing a gruesome injury that saw him break his left ankle last May against the Seattle Mariners, he still finds time for those he sees need it.
“I’m so happy that I’m able to be 100% back this year,” Cabrera said. “I’m working to get stronger, to do a lot of things that I can to help the team get the ring this year. So you can’t imagine how happy I feel about it.”
His background is extensive, and his ability to learn nearly every position on the diamond is uber impressive. He only played two minor league games in right field, yet he robbed a home run in his first career MLB game out there.
This was something that he stressed to the kids as well, that versatility is important to allow the manager more opportunities to put them into the game.
Cabrera’s Road to the Show
Adversity is nothing new to Cabrera, hailing from Guarenas, Venezuela. He had to fight to be recognized by MLB clubs when he was a teenager. His perseverance paid off when he was signed by the Yankees as an international free agent in 2015. He made his MLB debut in 2022, and 2026 will mark his 12th year with the Yankees organization.
A guy who has battled like that is something that really resonates with JustinTime Baseball, and it’s why he is beloved by their entire company.
“I want the players to really be in touch, to literally touch and feel and see that these MLB players had the same journey as you,” Sherman said. “So really to show them what’s possible. That’s really the whole point of these clinics, and to give an amazing, excellent experience with our excellent coaches.”
Oswaldo Cabrera is looking forward to being back on the diamond with his teammates as the Yankees begin the 2026 season in less than a month with spring training starting up – Image Credit: Bill Menzel/Latino Sports
On the diamond, Cabrera has also fought highs and lows, seeing a lot of success in his first season, but taking a step back in 2023. In 2024, he rebounded and helped the Yankees appear in the World Series.
“So proud of everything that’s been happening and, obviously, made me get more motivation about myself to get better and to keep working to stay at this level for a while,” Cabrera said.
The bottom line is that Cabrera is still looking for more, which includes that championship the Yankees have been chasing since 2009.
Oswaldo Cabrera, working his way back to 100% on the diamond, believes this year in the Bronx could make for a special season – Image Credit: Latino Sports
“Every year is different for sure, but I know this year, everybody has the same mentality, and everybody is so committed to make this year happen and do the things that we want, which is to get that ring back to New York,” Cabrera said.
For more information on JustinTime Baseball and Sherman’s clinics, visit JustinTimeBaseball.com and also to keep up on social media, check out his platforms @JustinTimeBaseball on Instagram and @JustinTimeBase1 on Twitter.
He wouldn’t be where he is today without several notable sponsors, which include Chestnut Market, Beau Monde Builders, American Legends, Let’s Go Trivia, Di Paterio Contracting, Slide MVP, Cross River Dental, and Veterinary Emergency Group.
Follow us on Social Media for updates and exclusive content
Instagram: @latinosportsoficial
Facebook: Latino Sports
Twitter: @latinosports
