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After falling short of 90 wins and stumbling out of the playoffs in two contests, the Blue Jays have some work to do this winter.

They've got holes in the lineup, plenty of pending free agents, and some relationships to repair with key players. Here are three of Toronto's biggest challenges this offseason:

1. Figuring Out Third Base

Even with his up-and-down season, Matt Chapman's pending free agency will leave the biggest hole in Toronto's 26-man roster this winter. The 30-year-old posted seasons of 3.5 and 4.4 WAR in his two years with the Jays, leaving Toronto with some real production to replace if Chapman cashes in elsewhere this offseason.

Cavan Biggio, Santiago Espinal, and Davis Schneider all chipped in at 3B last year, but none seem like a 162-game solution at the position. Prospects Orelvis Martinez and Addison Barger hit well in Toronto's upper minors in 2023, but handing the 3B keys to a raw rookie would be bold for a team hoping for a World Series run. So, the Jays will likely go outside the organization to address third base — but the pickings there are slim.

Beyond Chapman, the free agent class thins fast at the hot corner. Guys like Max Muncy, Justin Turner, and Jeimer Candelario are better suited at 1B or DH, leaving Gio Urshela as the only regular third baseman expected to hit the open market who posted higher than 2.0 WAR in the past two seasons, combined. 

Toronto can hit the trade market, but they won't be alone in that department either. There are several other competing teams that will need new 3B this winter — the Cubs, Yankees, Giants, and Diamondbacks to name a few.

2. Navigating The Payroll

The Blue Jays increased their Opening Day payroll by over $30 million each of the past two seasons, but that rapid spending growth may start to slow in 2024. Team CEO Mark Shapiro noted he expects Toronto's payroll "to stay in the same area," during his season-end press conference last week, signaling the Jays will probably come in close to the $209 million mark they opened 2023 at again next season.

It's a high number, for sure, ranking seventh in baseball. But, it's going to force Ross Atkins and company to get creative this winter. 

Given significant projected arbitration raises for players like Vladimir Guerrero Jr., Jordan Romano, and others, much of the room freed up from the departures of Chapman, Brandon Belt, Hyun Jin Ryu, and Kevin Kiermaier is already spoken for. Even already-inked players like Kevin Gausman, Chris Bassitt, and Bo Bichette will see raises of at least $3 million next season, due to deal structures.

Barring any major non-tenders, the Jays' 2024 26-man payroll is currently projected to sit just under $190 million — $19 million off their 2023 Opening Day mark. If the budget stays in the same range as last year, free agency can't be the solution for all of Toronto's roster holes this winter.

3. The Alek Manoah Situation

It's safe to say Alek Manoah's 2023 season didn't go as planned.

The young starter posted a 5.87 ERA in 19 starts, was optioned to the minors twice, and was nowhere near the MLB team for the final month of the season and playoff push.

While Manoah willingly reported to the team's Florida Complex when he was first optioned in the middle of the season, when the team sent him back to the minors in early August things didn't go as smoothly. The righty initially didn't report to Triple-A Buffalo and never pitched for the Bisons. Eventually, the righty's season ended with shoulder injections the team wasn't in complete agreement with.

“Any time a pitcher of his success is optioned, it’s a very difficult thing to stomach and he disagreed with the decision,” Atkins said after the 2023 season. “So that created some frustration.”

It's nearly impossible to say how the Jays can or should manage the Manoah situation this offseason. He hasn't asked for a trade, Atkins confirmed last week, but can the Jays reasonably expect him to come back and perform in 2024? If he's 2022 Manoah, who posted a 2.24 ERA and almost won the Cy Young, the Jays need to have a rotation spot available to him. If he's 2023 Manoah, they need other options.

If the Jays decide to enter 2024 with a rotation spot earmarked for Manoah, they'll need to have plenty of flexible backup plans and pitching depth. Bowden Francis and Rickey Tiedemann could be those options, but the Jays probably need to add some more depth this winter while simultaneously repairing things with Manoah.