Losing in the playoffs means a long offseason of asking questions and wondering what might have been. That’s especially true for a team like the Chicago White Sox, who squandered a 2-0 lead in the ALDS and will now be watching the rest of the postseason from home.

A lot went right for the White Sox in 2026. In many ways, it was a magical season, even if it ended in frustrating fashion. That being said, White Sox fans can’t help but feel like this team could have done more with the opportunity in front of them.

After all, being one win away from the ALCS doesn’t come around very often. And had Chicago approached things differently at the trade deadline, for example, we might be talking about a very different outcome right now.

The past is the past, though. All the White Sox front office can do now is prepare for the future.

But as we turn our attention to 2027, there’s plenty of uncertainty surrounding Major League Baseball. Between the possibility of a lockout and questions about what the free-agent and trade markets will look like this winter, it’s difficult to predict exactly how the offseason will unfold.

Regardless of those circumstances, there are plenty of major questions staring the White Sox directly in the face.

There’s an elephant in the room when it comes to Munetaka Murakami, the Japanese sensation who looked like one of baseball’s most prolific power hitters during the early stages of 2026.

At the All-Star break, it felt like a no-brainer that the White Sox should extend Murakami long-term and build around him as one of the faces of the franchise.

But now there are serious doubts, and for good reason.

From the beginning of August through the end of the regular season, Murakami appeared in 53 games for the White Sox and hit just .156. He also struck out in nearly half of his at-bats, recording 92 punchouts in 192 at-bats during that final stretch.

Unfortunately, some of those struggles carried over into the postseason.

Murakami showed just how capable he is of changing a game with one swing in Game 1 of the ALDS, launching a two-run home run off Parker Messick. The rest of the series, though, showcased the ugly side of Murakami’s game.

In Games 3 through 5, as the White Sox squandered their series lead, Murakami went just 1-for-11 with eight strikeouts.

That included a bases-loaded opportunity with two outs in Game 5, when Guardians reliever Eric Sabrowski took the simple approach of throwing fastballs right over the plate and watching Murakami swing through them for a strikeout.

The more we saw of Murakami, the more concerning his contact issues became. And as we head into the offseason, those struggles make the possibility of a contract extension much more difficult to navigate.

The White Sox don’t know exactly what Murakami is at this point. I’m not sure anybody does.

Is this simply a matter of Murakami needing to make adjustments over the offseason to look more like the hitter we saw in the first half? Or has the league adjusted to him in a way that could make a batting average below the Mendoza Line the norm moving forward?

Would Chicago be comfortable giving Murakami a five-year, $100 million contract right now? I’m not sure I would be. And I’m not convinced Murakami would accept much less when he has the opportunity to bet on himself in 2027.

Some White Sox fans have suggested that Murakami’s second-half struggles could actually benefit the organization in the long run. If his disappointing finish allows Chicago to negotiate a cheaper extension, perhaps the White Sox could secure a team-friendly deal that pays dividends for years to come.

I understand the thought process, but I’m not sure that’s a realistic outcome from Murakami’s perspective.

He obviously wants to be paid like one of Major League Baseball’s biggest stars. And if he genuinely believes he has 45-home-run seasons and the kind of production we’ve seen from players like Kyle Schwarber and Pete Alonso in his future, why would he settle for a discounted contract now?

He can spend 2027 proving that he’s capable of making the necessary adjustments and cash in afterward. And if things don’t work out, he can explore a shorter-term deal or other opportunities when the time comes.

The fact of the matter is that it became far too easy to strike out Murakami down the stretch. He wasn’t providing the kind of protection in the middle of the lineup that the White Sox needed from him, and his inability to consistently put the ball in play became a glaring weakness.

There’s still plenty of reason to believe in Murakami’s upside. His power is undeniable, and we saw firsthand how dangerous he can be when he’s making contact. But committing nine figures to a player with such significant swing-and-miss concerns would be a considerable gamble for the White Sox.

Murakami will be on the Opening Day roster and remain a key piece of Chicago’s lineup in 2027. Beyond that, though, his future with the organization is uncertain.

And I’m not convinced we’ll get an answer this winter.