Four internal questions the Blue Jays will need to answer this offseason

Looking at Possible Trade Chips this Offseason
While this winter does not boast many names heading to the free agent market, the following offseason is a completely different story.
Hyun Jin Ryu, Matt Chapman, Lourdes Gurriel Jr., Teoscar Hernández, Adam Cimber, Raimel Tapia, and Anthony Bass will all become free agents that year, with the club also needing to decide whether to pick up options on Yimi Garcia (club option at $5 MM) and Whit Merrifield ($18 MM mutual option). Looking at the committed money heading into 2024, the Jays have almost $66 million in luxury tax salary tied up in Springer, Gausman, and Berrios, with another $12 owed to Kikuchi, who will be on the last year of his deal.
Assuming the club picks up Garcia and does not pick up Merrifield, the luxury tax salary will sit at around $80 million, which is a solid chunk of change to play with (not including arbitration). That being said, the Jays should be looking to extend some young stars (as I mentioned earlier) and that will cost a pretty penny.
Looking at the Blue Jays money ahead
Thinking on the high side, if the Jays have Bichette and Guerrero Jr. locked up for $55-$60 million combined, they are sitting at $140 million, but that’s not including other player arbitration values, which will include the likes of Cavan Biggio, Santiago Espinal, Danny Jansen, Jordan Romano, and Alejandro Kirk (again, assuming Bichette and Guerrero are already locked up).
That could push the value up another $30-$40 million to the $170-180 million area, which could tie the hands of the front office when considering extending pending free agents in Chapman, Gurriel Jr., and/or Hernández. All three players will be eligible for the qualifying offer as well, meaning if they leave and don’t come back, the Jays could gain draft pick compensation, but it might be tough to retain all three without having cash/salary space for other areas on the roster unless Rogers is willing to go past the luxury tax.
That being said, the Jays’ front office could move one of Gurriel Jr. or Hernández this offseason, although it would be a tough decision given how they played this past year and how they are revered by the fanbase, but if the money isn’t there to extend them, it might make future moves easier for the franchise. Again, the numbers I put forward are hypothetical (and also rely on the Jays extending two young stars) but even if they don’t sign extensions, they will still command a strong chunk of change in arbitration anyway which will still drive up payroll.
Next. Jays: Another Season in Window of Contention Ends Abruptly. dark
Factor in non-financial decisions like what the Jays will do with three MLB-ready catchers on their roster, and the club might be making some tough moves this offseason.