Blue Jays Nation’s Top 20 Canadian Baseball Prospects for 2025 – #7: Myles Naylor

Blue Jays Nation’s countdown of the top Canadian baseball prospects continues with a familiar last name who could be in for a breakout season in 2025.

#7 Myles Naylor

Hometown: Mississauga, Ont.

Organization: The Athletics

Position: SS/3B/2B

Acquired: 1st round, 2023 draft (OAK)

When the Oakland A’s drafted Myles Naylor in the 2023 draft, a third and final Naylor brother joined professional baseball. All three attended St. Joan of Arc Catholic School in Mississauga, Ont. and played for the Ontario Blue Jays, with the elder two quickly making a name for themselves at the highest level.

Josh was taken first back in 2015 (12th overall) followed by Bo in 2018 (28th). Despite Myles being selected 39th, his at-slot signing bonus of $2.2M was comparable with his brothers, who signed for $2.25M and 2.58M, respectively. The Naylors will try to become just the 16th trio of brothers to play in the Major Leagues, with the latest being Yadier, Jose, and Bengie Molina. As the Society of American Baseball Research explains, there’s also been one quartet of brothers (the O’Neills) as well as one quintet (the Delahantys).

With Josh and Bo developing into starters in their first couple of years in the major leagues, it’s fair to assume that Myles won’t be too far behind. However, his struggles in his first taste of pro ball may lead to him taking longer than expected to reach the major leagues.

Hey @CleGuardians, we’ve got a Naylor who can hit homers too 💪

No. 8 @Athletics prospect Myles Naylor — younger brother of Josh and Bo — drills a three-run shot for the @stocktonports. pic.twitter.com/NQVeTiVYjE

— Minor League Baseball (@MiLB) May 1, 2024

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Naylor’s professional career thus far

It’s not very often that teams end up pushing their draft picks to affiliated ball in the same year that they were drafted. The Athletics saw an advanced enough approach from Naylor to move him to single-A after just two games in Rookie Ball. Across 32 games in Stockton, the then 18-year-old slashed .208/.280/.375 while struggling with strikeouts (39.4% strikeout rate).

In his first full season last year, he slashed .191/.321/.322, with a 34.7% strikeout rate. One positive was his overly selective eye at the plate, as he managed a 15.8 BB%, but still saw a K rate above 30%. Although the numbers may be underwhelming, it’s important to note that the youngest Naylor brother was over two years younger than his competition in single-A, on average.

It remains to be seen which position Naylor will ultimately settle into. He played all but one game at shortstop in 2023 but logged 14 starts at second base in 2024 (compared to 89 at shortstop). It’s worth monitoring whether the six-foot-two, 195-pounder logs any starts at third base as he fills into his body in the coming seasons.

Naylor’s ceiling

Although he wasn’t expected to have the same bat-to-ball skills as his brothers, his power potential had scouts excited coming into the draft, especially for a middle infielder. That power hasn’t translated to many home runs thus far, but there’s hope that his numbers may reflect his talent in the coming years.

Prospect of the day #1: Myles Naylor, No. 9 prospect in the A’s system…

Brother of Josh & Bo, ‘23 CB pick. 10 HR, 69 BB, 137 K in 96 MiLB games this year.

Bringing this series back! pic.twitter.com/OSxS2Uu69p

— Sam Fosberg (@discussbaseball) August 13, 2024

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It’s clear that he has the potential to develop into a major league starter, but he will have to prove himself at several spots before he can work his way up. The biggest thing for him to reduce his strikeout rate will be to have a better handle on off-speed pitches, where a lot of his swing and miss came on last year. Given his patient approach at the plate, a reasonable increase in his contact rate could allow him to take off in 2025.

The Mississauga natives’ defensive skills may allow him to stick at shortstop for the short term, but a move to third base appears to be best for him in the long run. It may take a couple of years, but if all breaks well, the youngest Naylor could settle in as a 20-25 home run guy who gets on-base at a high clip and plays quality infield defense.

Where does he play in 2025?

Given his struggles in Stockton over the last season, it’s fair to assume that he may be ticketed for a return to single-A. If he does well over the first month of the season, it shouldn’t be too long before he’s moved up to high-A.

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