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.

This month hasn’t been kind to Blue Jays fans.

The Wild Card Series loss in Minneapolis still lingers, and watching the duo of Gabriel Moreno and Lourdes Gurriel Jr. make a run to the World Series with the D-backs hasn’t exactly helped.

Let’s get that clunky conversation out of the way first. Hindsight can be a wonderful thing, but let’s not rewrite history. It’s important to acknowledge the original analysis of any move, and in the days following this trade last December, I viewed it as a sensible enough deal for the Blue Jays that carried an extreme risk.

Daulton Varsho fit the Blue Jays’ vision for their 2023 rebrand so well. They wanted to defend better, run better and do all of the small things right. Varsho checked every box at the time, but then the season started and the grand vision didn’t come together as seamlessly as anyone hoped. The risk all along was that the Blue Jays could lose sleep for a decade over dealing a perennial All-Star catcher at a young age. That might just happen.

There’s a sense of “longing for the one that got away” here, which is understandable. So many prospects break your heart, so it’s difficult to see them shine elsewhere. The boring answer here is that there needs to be some room for a middle ground. Yes, trades need years to be judged, but that doesn’t mean we sit and wait until 2027 to pass any judgment. Year one matters.

Varsho can still be an important piece of what the Blue Jays do, potentially playing a Gold Glove-caliber center field next season, but Moreno has the talent and potential to make this trade a painful one in years two, three, four and beyond.

Now, for the questions facing this Blue Jays team entering a crucial offseason:

Is it time to pivot (again)?

In the simplest terms, the Blue Jays swapped out offense for pitching and defense a year ago. Their pitching and defense was excellent, particularly the rotation, but the bats weren’t enough.

The sensible move here is to move back in the old direction. It’s rare to see teams pivot identities like this, but the Blue Jays clearly need a larger, philosophical change. This lineup needs more power to steal games with, and while some of that must come from within (his name is Vladimir Guerrero Jr.), Toronto needs to bring more in.

Who is Alek Manoah?

A year ago at this time, Manoah was coming off a dominant season and was about to finish third in American League Cy Young Award voting. Today? There’s no certainty that Manoah will open 2024 in the rotation … or with the organization.

Manoah’s season, including his struggles and medical tests late in the summer, was extremely tangled and complicated. Beyond the pitcher, there is a relationship that needs to be rebuilt. If Manoah can come into camp and re-establish himself as a solid back-end starter who eats innings, then everyone wins, but this could go 100 different directions.

There is no bigger variable on this roster right now.

How much can the Blue Jays trust their prospects?

Let’s lump together Davis Schneider, Addison Barger, Orelvis Martinez, Spencer Horwitz and Ernie Clement. Eventually, you can add No. 7 prospect Alan Roden to this list. That’s six names internally, and the Blue Jays should have three or four position player spots to fill.

This organization doesn’t need four of these players to show up to Spring Training as superstars, but someone needs to win a job. Schneider is the likeliest, of course, but beyond the “baseball” side of this, it’s about money.

If the Blue Jays can fill two of their holes internally instead of via free agency, that could save them millions, allowing them to focus their money on landing a star instead of two “good” players. That’s an attractive route for Toronto.

What does "transparency" actually look like?

What finally came out of the Wild Card mess and the move from José Berríos to Yusei Kikuchi in Game 2 was a realization that the Blue Jays need to communicate better.

“There needs to be a higher level of transparency and communication with our players in our preparation and game-planning process,” said team president and CEO Mark Shapiro.

That’s difficult to envision in baseball terms. What does transparency look like on a baseball field, in an actual game? Ideally, the long-term answer is players who look more comfortable and make better in-game adjustments. This will take work from both sides, and there’s a level of trust involved here, particularly for a player like Berríos or the many Blue Jays in their clubhouse who said they were surprised when that move was made.

This is the toughest theme to grasp this offseason and we won’t see results until months into the season, but it’s critical that the organization addresses this in a way that players can feel and understand.

Who is in line for an extension?

Let’s start with Bo Bichette and Guerrero, who are now two seasons away from free agency. That coincides with the back ends of some large contracts and the usual declines that naturally come along with those years for veteran players, so the stakes are high.

“The priority is to sustain the opportunity to win,” Shapiro said. “As it pertains to where individuals fit into that, I’ll leave that to [general manager] Ross [Atkins] to discuss, but we’ve got to do everything possible to keep that window open.”

If the Blue Jays look to extend Guerrero, who are they signing? Guerrero’s camp will rightfully point to his potential and the 2021 season that captured it while the Blue Jays will point to the reality of the past two seasons, which paints the picture of a good hitter who is leaving some potential on the table. That’s how these things work, and the closer Guerrero and Bichette get to free agency, the more appealing it will be for them to hit the open market at their age. Guerrero will be 26 when he hits free agency, and Bichette will be 27.

Danny Jansen belongs in this conversation, too. A free agent after 2024, Jansen needs to be considered alongside these core pieces more often. His injuries are a factor, but with so many of those coming on “bad luck” plays (tipped balls, hit-by-pitches), there’s reason to believe there are healthier days ahead. Jansen is beloved in that clubhouse and by many in the front office. Extending him should be a priority.