White Sox Have A Real Rotation Upgrade Fans Will Want Debated

As the White Sox eye a second consecutive postseason berth, acquiring Cubs southpaw Shota Imanaga emerges as a savvy move to bolster their rotation.

The White Sox are still in the middle of their 2026 season, but the offseason conversation is already starting to take shape - and the biggest need is hard to miss. Their starting pitching has been shaky, and that’s exactly why free agency could become the cleanest way to patch the hole.

Tim Kelly of Bleacher Report pointed the White Sox toward a familiar name on the North Side: left-hander Shota Imanaga. The fit makes sense on paper, especially for a club trying to build on its momentum and stay in the postseason mix in 2027.

"Sean Burke and Davis Martin are a nice one-two punch, but there's not necessarily a slam-dunk starting pitching prospect near the majors," Kelly writes. "So adding Imanaga could help the White Sox make a second consecutive postseason appearance in 2027."

Imanaga’s profile is exactly why he stands out as a realistic target. Over three seasons with the Cubs, he has logged 86 starts and posted a 3.45 ERA. This year, he worked 174.1 innings across 32 starts, finishing with a 3.77 ERA and an 11-10 record.

That kind of production would give the White Sox a clear upgrade without requiring them to chase the sort of blockbuster arm that may be beyond their reach. Tarik Skubal, for example, is probably too expensive for them, but Imanaga looks like the type of free-agent starter who fits both the roster and the budget.

For a White Sox team that has already turned 2026 into a wildly successful year, the next step is obvious: keep the rotation moving forward. Adding at least one starter this offseason would be a smart move, and Imanaga checks a lot of boxes as a left-handed arm who could strengthen the group in 2027.

Kelly’s connection of Imanaga to the White Sox is a sensible one. He may not be the loudest name on the market, but he’s the kind of underrated starter who could make a real difference.

In Other News...

Jerry Reinsdorf Just Framed This White Sox Run Very Differently

Jerry Reinsdorf took a step back after the White Sox knocked off the Astros in the American League Wild Card Series and drew a much broader picture of where this 2026 season sits in the franchises arc. The chairman pointed to the hiring of general manager Chris Getz and the way this young roster has moved from promising to postseason-ready faster than many around the team expected.

Now the White Sox have earned a matchup with the Guardians in the AL Division Series after finishing one game behind them in the American League Central. For a club that has spent recent seasons trying to reset its direction, the run has already changed the conversation, even before the next round begins. [Read more 🡒]

Red Sox Crochet Trade Suddenly Looks Worse After Boston's Early Exit

The White Soxs own postseason run has already given the organization some validation, and so has the return from the Garrett Crochet trade made two years ago. Chicago advanced past the Astros in the AL Wild Card round, and three of the four players it received in that deal played meaningful roles in getting the club there, a reminder that the haul has mattered when it counted most.

Bostons early exit only sharpens the contrast. Crochet had a rough outing in the Red Soxs elimination game against the Yankees, and while Chicago is moving on to face the Guardians in the ALDS, the trade package once viewed through a long-term lens suddenly looks a little more immediate, and a little more favorable, from the White Sox side. [Read more 🡒]

Red Sox Sweep Just Sparked A Frustrating Debate Fans Know Too Well

The Red Soxs sweep has reopened an argument that never really disappears in October: how much a manager should lean on the numbers when the margins get thin and the pressure gets louder. Bostons players were candid afterward about concerns with managerial decisions and the clubs dependence on analytics, a conversation that tends to flare up any time a season ends abruptly. It is the kind of debate that follows teams long after the clubhouse empties, especially when a loss feels like it was shaped as much by choices as by execution.

For Chicago fans, it is a familiar reminder of how differently a postseason can feel from one season to the next. The White Sox finally broke through with their first postseason series win since 2005 and now move on to face the Cleveland Guardians in the ALDS, while the Cubs were swept by the Padres and head into the winter with their own questions. In a week when the Phillies and Braves are headed to a deciding game, the contrast across the state lines is hard to miss: one Chicago club gets to keep playing, and the other is left watching the same old argument play out somewhere else. [Read more 🡒]