Extensions? Retool? What lies ahead for Blue Jays in 2024

This story was excerpted from Keegan Matheson’s Blue Jays Beat newsletter. To read the full newsletter, click here. And subscribe to get it regularly in your inbox.

TORONTO -- There are 65 days until the Trade Deadline on July 30.

That’s a big day for any organization, any year, but this one feels like it could be a true pivot point for the Blue Jays as an organization.

Now 23-28 two months into the season with an offense that’s dragged behind this club like an anchor, the Blue Jays have these 65 days -- or most of them, anyways -- to get back on track and avoid some uncomfortable decisions. This roster is absolutely built in a way that could allow one more run with this current core in 2025, but this roster also needs to convince the front office of that, first.

Earlier this week, our Mark Feinsand spoke with an AL executive who believes the Blue Jays could move one of Vladimir Guerrero Jr. or Bo Bichette this summer.

“I don’t think they’re opposed to it,” an AL executive told Feinsand. “They’ve talked to teams about it. The asks were ridiculous, but I think they’re going to try to retool a lot, and using those guys to get pieces may be the way to do it.”

The stakes aren’t usually this high in late May. To say that their window is closing is too simple and too rigid, but the window is certainly a different size and shape than it was two years ago. The Blue Jays have so much to consider over these next two months, both in the short and long term.

Push, pivot or pull back?
This road splits into three paths … eventually.

In all of this, we must remember 2015, when the Blue Jays were 50-51 on July 28. They traded for Troy Tulowitzki and David Price, among others, and went 43-18 the rest of the way, an unforgettable stretch of baseball in this city. This current roster would need to show this front office a lot in the coming two months to justify such an aggressive push, and this organization’s appetite for risk doesn’t feel nearly as large as it did back then, but you know what they say about desperate times. …

If the Blue Jays find themselves on the outside looking in? That’s when this gets trickier. Would the Blue Jays be so bold as to move on from Vladdy or Bichette? Or would they choose to deal pending free agents for one last crack with this core in 2025?

Free agents after 2024: Yusei Kikuchi, Danny Jansen, Yimi Garcia, Justin Turner, Kevin Kiermaier, Trevor Richards

Free agents after 2025: Guerrero Jr., Bichette, Chris Bassitt, Jordan Romano, Chad Green, Tim Mayza, Cavan Biggio

This can still go in so many different directions, but you don’t need to squint to see that the Blue Jays could take an off-ramp soon if things don’t improve.

What about extensions?
Extension talks with Kikuchi or Jansen, as examples, are extremely unlikely amid all of this.

Kikuchi has earned himself a nice market this coming winter and Jansen, if he stays healthy, will hit free agency at his peak. The Blue Jays could use both back -- particularly Jansen, who is so important to this franchise -- but the market will set the price, not the Blue Jays.

The more interesting decisions come a year from now, of course. Guerrero still feels like the likelier of the two to stay in Toronto, for what it’s worth, but unless Guerrero miraculously rediscovers his 2021 form, his market won’t be close to what we expected a couple of years ago. That’s already feeling like a situation where the Blue Jays could slowly let his market play out.

Who’s next? The farm system
There have been a few success stories on the prospect front this season, particularly in Buffalo, but this system entered the season ranked No. 24 by MLB Pipeline and that hasn’t changed much.

“We’ve had some really encouraging things in Double-A [New Hampshire] and Triple-A [Buffalo], but had some young pitchers get hurt,” said general manager Ross Atkins. “On the offensive side, it’s really encouraging. Some of our pitching is doing well, but obviously our higher guys have taken some injury hits.”

The Blue Jays are stacking up some high-upside prospects -- think Arjun Nimmala (No. 3 prospect), Enmanuel Bonilla (No. 8), Landen Maroudis (No. 12) -- but they need more and more and more. Regardless of how the next 18 months play out, the Blue Jays need to position themselves better for the seasons beyond that and it begins on the farm.

Do the Blue Jays believe they have their next Bichette? If not, they need to find him.