A 17-year-old Owen Caissie dug into the batter’s box for the Canadian Junior National team late in an exhibition game against the Toronto Blue Jays at TD Ballpark in Dunedin, Fla., on March 12, 2020, with a big opportunity. Caissie, who was hitless on the day, jumped on an early offering from veteran minor league pitcher Connor Overton and crushed it.
“He got it good,” said Canada manager Greg Hamilton.
Caissie got it really good. The left-handed hitting slugger launched the fastball to deep centerfield. The ball cleared the fence and into the batter’s eye of the park for a home run that Hamilton estimates traveled well over 400 feet.
“It was an eye-opener for a lot of people,” Hamilton said.
Caissie has possessed that type of power for a long time. It’s a big reason the San Diego Padres drafted him later that year and why the Chicago Cubs eventually acquired him in a trade. That power is why the 22-year-old is now ranked as the top prospect in Chicago’s organization, according to MLB Pipeline.
“It’s not that surprising that he’s doing well,” Hamilton said.
Hard work leads to a lot of power for Caissie
Caissie has been working on his power for years. When he was a little kid, he hit off a tee that his dad, Jason Caissie, set up in the family’s garage. Owen Caissie watched highlights of Major League Baseball stars, including Barry Bonds and Aaron Judge. He studied their techniques and stances, trying to figure out where they got their power from.
He implemented it into his swing and started recording his hacks so he could evaluate them. When Caissie was just 10, he began getting lessons with coaches from the Fieldhouse Pirates, an elite baseball club in Canada. Jimmy Richardson, the director of baseball operations for the club, could tell Caissie had a big bat right away.
“He had an incredible ability to get the barrel to the ball, even at that age,” Richardson said.
Some of that came from a natural ability. But the bulk of it came from the work Caissie was willing to put in. Even back then, Caissie was willing to work as hard as possible to become a star player. He became a regular at the Pirates’ indoor facility, coming in seven days a week by the time he was just 12.
The work produced big-time results with Caissie clobbering baseballs further than any of the other kids his age. Jason Caissie remembers his son belting one during a game that landed about 60 feet beyond the fence. He estimates it traveled 370 feet. Owen Caissie was just 14 at the time.
The success only made Caissie work harder. He spent most of his days training at the facility. After school, he’d ride his bike over and hit for a few hours. Caissie then got a break when his parents picked him up for dinner. Later in the evening, he returned for practice for several more hours with the Pirates.
Even after those practices ended, Caissie stuck around, sometimes staying as late as midnight to get as many extra swings in as he could. He stayed so late that he sometimes locked the facility for the night. That became the norm throughout high school.
“I didn’t party,” Caissie said. “I didn’t go to a single high school party. I was just in the cage all the time with a bunch of buddies and that’s all we did, really. I wouldn’t have it any other way.”
Caissie’s relentless work ethic paid off. By the time he turned 16, he was popping on the radar of college coaches. The Burlington, Ontario, native traveled to the United States with his teammates from the Pirates to compete in Prep Baseball Report tournaments.
During a dominating performance at one of the tournaments, Caissie earned a scholarship offer from Kentucky. Caissie committed, but it didn’t last. As he got older, his swing got better and his body got bigger. He grew into his frame, shot up several inches and added 25 pounds one season.
The power hitter put his talents on display during the Tournament 12 showcase at Toronto’s Rogers Centre in 2019. Caissie won the event, hitting balls into the second deck of the Blue Jays’ stadium, Hamilton said.
When Caissie reopened his recruitment, some of the top college programs from across the United States started reaching out to him. He eventually committed to Michigan, but Caissie’s stock continued to soar throughout high school. The peak may have come during the exhibition game against the Blue Jays.
He was hitless early in the game. Then he belted the home run against Overton, a long-time minor-league pitcher who eventually went on to pitch in the big leagues. Hamilton believes Caissie showed the ability to not only hit pro pitching, but do it at a high level with a wood bat. He believes that it likely helped Caissie’s draft stock.
Caissie agrees.
“I think it really helped my career,” Caissie said. “Jumpstart it for sure.”
The Padres selected Caissie in the second round of the MLB Draft three months later. But the hard work Caissie was putting in didn’t stop after making it to professional baseball.
Caissie gets traded and continues to deal with trade talk
Caissie was back in Canada training at the Fieldhouse Pirates facility in December of 2020 when his phone rang. It was his agent letting him know he may be traded. Caissie took a few minutes to digest the information. Then he did what he usually does. He went back to work.
“I just got drafted, so I didn’t really have any real connections to the Padres,” Caissie said. “I hadn’t really established a super deep connection with them. So, it was kind of crazy.”
Caissie was part of a deal that sent Zach Davies, Reginald Preciado, Yeison Santana and Ismael Mena to the Cubs for star Yu Darvish and Victor Caratini. The Cubs quickly got a look at the power that Caissie had. During his first season of professional baseball, he hit .302 with 11 doubles and seven homers in 52 games across two levels.
The following season, Caissie helped High-A South Bend to a championship. During one game, he smashed a home run that went out of the stadium and over a workout barn. The ball bounced past two buses in the parking lot and was brought back to the dugout, where it was given to Caissie’s dad.
“He absolutely crushed it,” Jason Caissie said.
That was just a sign of things to come for Caissie, who hit .289 with a .917 OPS and 22 homers for Double-A Tennessee in 2023. He made his Triple-A debut in 2024 and became one of the best hitters in the Cubs organization, hitting .278 with 29 doubles and 19 homers.
The success earned Caissie an invite to play in the 2024 All-Star Futures Game, a contest that features some of the best prospects in Minor League Baseball. An injury kept Caissie from playing in it, but it didn’t slow him down. After the season, Caissie was placed on the 40-man roster by the Cubs.
While Caissie possesses a strong arm, plays some good defense and can run the bases well, it’s his power that makes him so valuable. Cubs officials have said over the years that Caissie has boasted not only some of the best exit velocity numbers in baseball.
“From a bat speed perspective and the way he squares a ball up, I mean, he’s 107, 108 consistently,” said Iowa manager Marty Pevey.
Caissie has continued doing it. Despite battling injuries and a sickness recently, Caissie has put together another strong season in Triple-A. During his first 65 games with Iowa this season, Caissie tallied a .876 OPS with 18 doubles and 12 home runs.
The recent run of success has moved Caissie into the top spot in the organization’s prospect rankings and he was recently invited back to the All-Star Futures Game. With how well he’s performed, Caissie has constantly been at the center of trade rumors the last two seasons.
This season is no different, especially with the Cubs searching for help down the stretch. Caissie is one of the team’s top minor league commodities and could be on the move again before the trade deadline. He’s trying to tune all the talk out and said that last year, he even got rid of his Twitter account.
“I really just try not to look at it and just play baseball because you can try and play GM, but that doesn’t work,” Caissie said. “It never works. You can think what you want to think, but nothing is really set and final until it actually happens or it doesn’t. So, I really just try to play ball and just come to the park every day and have a good attitude.”
That positive approach has been a part of Caissie’s game for a while. Richardson said that following Caissie’s 2023 season, the slugger returned to Canada and traveled with the Pirates for their annual college fall trip. After enduring a full season in the minors, Caissie hopped on a bus with the young players and coaches for about two weeks while they traveled around playing games. The bus rides would sometimes be as long as 12 hours.
Caissie, wanting to help mentor a new wave of Canadian players, gave them advice, picked up meal tabs and even bought a phone battery when one of their phones died. The team would spend as many as 10 hours a day at the field. Caissie voluntarily joined in.
“He’s just a first-class human being,” Richardson said. “He’ll give the shirt off his back if he thought it was going to help somebody.”
Caissie is also an elite worker. Which is why it may be only a matter of time before he finally reaches the big leagues.
“He’s the hardest working person I’ve ever seen in my life at anything,” Richardson said. “I’ve been doing this for 15 years and there is no one that comes close to matching his work ethic that has ever come through our program. We’ve got pro guys from other organizations that come in, in the offseason as well and he’s just wired different than 99% of the population.”
Tommy Birch, the Register’s sports enterprise and features reporter, has been working at the newspaper since 2008. He’s the 2018, 2020 and 2023 Iowa Sportswriter of the Year. Reach him at tbirch@dmreg.com or 515-284-8468
This article originally appeared on Des Moines Register: Iowa Cubs outfielder Owen Caissie one of the organization’s most powerful hitters
Reporting by Tommy Birch, Des Moines Register / Des Moines Register
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