Shushkewich: Past Canadian Futures Showcase HR Derby winners have turned pro

Okotoks Dawgs Academy and Junior National Team grad Tim Piasentin (Coquitlam, B.C.) is presented with the Home Run Derby champion belt by Toronto Blue Jays legends Edwin Encarnacion and Jose Bautista at last year’s Canadian Futures Showcase. Photo: Trevor Fitzpatrick

September 16, 2025

By Tyson Shushkewich

Canadian Baseball Network

The Canadian Futures Showcase begins today, with over 150 of the best high school baseball players from coast to coast descending upon the Rogers Centre.

It will be an action-packed four days as six squads face off against each other before the showcase concludes on Friday with a Home Run Derby and a championship game.

Scouts from big league squads and coaches/recruiting coordinators from post-secondary programs in Canada and the United States will pay close attention to the high school talent. With all of the game action, one particular event that stands out is the Home Run Derby, which precedes the championship game.

Watching dingers fly over the outfield wall is fun for most players. In this case, it’s an exciting event that includes bragging rights for the winner, as well as a prestigious championship belt and trophy bat, and zero hurt feelings for the pitcher. Hitting a home run at the Rogers Centre is a bucket list item for many fans and players alike, and for these teenagers, it’s a feather in the cap of their hopeful early careers in baseball.

However, under the surface, the Home Run Derby has a bit more meaning than just a belt and a bat for those who win the title, regardless of whether they know it or not. With the event’s introduction in 2019 (when it was called the T12 Tournament), there have been four winners crowned:

2019 – Owen Caissie (Burlington, Ont.)

2022 – Myles Naylor (Mississauga, Ont.)

2023 – Nathan Flewelling (Innisfail, Alta.)

2024 – Tim Piasentin (Coquitlam, B.C.)

One thing these winners all have in common?

They all found themselves drafted the following summer by a major league squad.

Caissie was with the Fieldhouse Pirates when he won the inaugural event, blasting 11 home runs in the final round to best Tyler Hinrikus (Waterloo, Ont.). Fast forward to the next summer, and Caissie found himself on the San Diego Padres radar, with the NL West squad drafting the outfielder in the second round. The Burlington product made his big league debut with the Chicago Cubs earlier this year.

Myles Naylor followed suit in 2022 when the event returned, this time in Ottawa at Raymond Chabot Grant Thornton Park due to scheduling conflicts at the Rogers Centre. He smashed 19 total home runs to win the event, clubbing 10 homers in the first round before adding nine more in the championship round to narrowly beat current Blue Jays prospect Sam Shaw (Victoria, B.C.).

Considering he has bragging rights over his brothers, Bo and Josh, when it comes to the derby hardware, the youngest Naylor followed Caissie when it came to the MLB Draft, with the Athletics selecting the Mississauga native in the first round (39th overall) in 2023.

Breaking the Ontario derby winners' streak was Alberta product Nathan Flewelling in 2023, who sent 11 total home runs over the Rogers Centre wall, finishing the championship round with six homers. The Tampa Bay Rays chose him in the third round the following summer.

Last September, the honours went to the West Coast and Tim Piasentin, who split his time between the Okotoks Dawgs and Junior National Team.

The left-handed slugger smacked a total of 22 home runs in the event, which resulted in a total of four rounds because he and Esteban Dessureault (Trois-Rivieres, Que.) kept going the distance, resulting in two overtime, 30-second swing-offs following the first two normal rounds. Piasentin would get the upper hand in the second overtime swing-off, collecting four jacks to Dessureault’s three to take home the honour.

Piasentin was one of the highest-ranking Canucks heading into this year’s big league draft, and the Toronto Blue Jays decided to keep him north of the border, using their fifth-round selection on the slugger.

Looking at the current roster for the 2025 showcase, a few names stick out for the Home Run Derby:

Easton Kitura (Spruce Grove, Alta.) / Vauxhall Jets Academy

Joey Khananisho (Kleinburg, Ont.) / Mississauga Tigers

Robert Omidi (Mississauga, Ont.) / Fieldhouse Pirates

Jalen Jacob (Maple, Ont.) / Ontario Blue Jays

Both Omidi and Jacob have experience in the event, with Omidi knocking six home runs last year while Jacob followed up with eight of his own in the first round before bringing in five more in round two for a total of 13, narrowly missing out on the swing off between Piasentin and Dessureault.

Considering this is one of the biggest showcases for talented high school players in Canada, it makes sense that scouts, coaches, and those across the various baseball circles tune into the games and events, such as the Home Run Derby.

Of course, there is no guarantee that winning the derby results in getting drafted the following summer. But considering each previous winner has found themselves heading into professional baseball the next year, it’s clear that winning the Home Run Derby at the Canadian Futures Showcase carries a lot of weight in the minds of pro baseball teams.

Hit the ball high and far, and many will take notice. Hit the ball high and far at the Rogers Centre, a better chance of receiving a summer bonus.