Proposed Blockbuster Cubs Trade Sees Chicago Deal Matt Shaw-Based Package for $300 Million Two-Time Cy Young Winner Tarik Skubal

By TJ Morin – 8 Hours Ago

The Chicago Cubs have been one of the most explosive teams this offseason, turning heads and significantly upgrading their roster to become one of the top teams in the National League. However, despite these impressive moves, they are still just one blockbuster trade away from truly being in the conversation as a top contender in Major League Baseball. A trade that could bring them to the next level has been proposed, with the Cubs looking to make a game-changing move for Detroit Tigers’ two-time Cy Young winner Tarik Skubal.

This proposal comes from Bleacher Report’s Zachary D. Rymer, who suggests that the Cubs should engage in a high-stakes trade with the Tigers, sending a package centered around Matt Shaw, the Cubs’ highly promising young infielder, to Detroit in exchange for the ace pitcher.

The Deal in Focus

Under the proposed trade scenario, the Cubs would receive:

• LHP Tarik Skubal

Meanwhile, the Tigers would receive:

• INF Matt Shaw

• RHP Jaxon Wiggins (Ranked MLB No. 58)

• OF Ethan Conrad

A Game-Changer for the Cubs’ Rotation

According to Rymer, the Cubs have already been significant winners this offseason, but right now they appear more poised to win the NL Central rather than taking down powerhouses like the Los Angeles Dodgers. The Cubs have made smart moves, but their rotation still lacks a definitive No. 1 starter. Currently, there is no clear leader to take the top spot in the Cubs’ rotation, and that’s where Skubal could dramatically change the conversation.

If the Cubs can land Tarik Skubal, they would immediately elevate their pitching staff. The left-hander, who has been nothing short of dominant over the past two seasons, would take the reins as Chicago’s ace, instantly transforming the Cubs’ pitching staff into one that could rival the league’s best. As Rymer points out, after the Cubs’ starters struggled with a strikeout rate of just 7.5 batters per nine innings in 2025, bringing in Skubal would be a breath of fresh air, adding the strikeout power the Cubs desperately need for a potential deep October run.

Skubal’s Incredible Track Record

In the 2025 season, Skubal posted an outstanding 13-6 record with a 2.21 ERA, an astonishing 241 strikeouts, and a WHIP of 0.891 in 195 innings pitched. His dominance on the mound was recognized with back-to-back Cy Young awards, making him not only a top-tier pitcher but also a franchise-changing player who could anchor the Cubs’ rotation for years to come. His ability to dominate on the mound would immediately make him the leader of Chicago’s pitching staff, providing the Cubs with a top-tier starter who can shut down offenses during the regular season and deliver when it matters most in the postseason.

The Catch: Detroit’s Demands

The one potential obstacle in this trade lies with the Detroit Tigers’ stance on trading Skubal. The Tigers have made it clear that if they were to part ways with their ace, they would need a proven MLB-ready pitcher to take his place in the rotation. Detroit is in a rebuilding phase, and adding a young, controllable starter would be essential for them to move forward.

For the Cubs, this means they would likely have to include one of their star pitchers in the deal—preferably one of their younger arms with control, which would give the Tigers a valuable asset for their future. Jaxon Wiggins, the Cubs’ No. 58-ranked MLB prospect, could play a crucial role in making this deal work. Wiggins has already shown glimpses of his potential, and his inclusion in the deal could provide the Tigers with the type of young arm they are looking for.

Why This Deal Makes Sense for the Cubs

If the Cubs can strike a deal with the Tigers, it would significantly boost their championship aspirations. Skubal’s presence would give the Cubs a true ace to lead their staff, something that would make them formidable contenders in the National League. The Cubs have already made significant upgrades this offseason, including adding key offensive pieces and improving their bullpen, but adding Skubal would make them a more complete team.

One of the key areas where the Cubs would benefit from this trade is the strikeout potential that Skubal brings. His high strikeout numbers over the past two seasons demonstrate his ability to dominate hitters, and that’s something that the Cubs’ pitching staff has lacked. In a division where the competition is tough and the stakes are high, having a pitcher who can go toe-to-toe with the best in the league is crucial for any postseason run.

What’s at Stake: Cubs’ Window of Opportunity

The Cubs’ window of opportunity is now. With the roster in place and the front office making aggressive moves this offseason, the time is right for the Cubs to go all-in. Their offense, led by key players like Seiya Suzuki, Ian Happ, and Cody Bellinger, has the potential to be among the league’s best. However, to truly compete with the top teams in the MLB, they need a top-tier ace to lead the charge on the mound.

A trade for Skubal would give the Cubs a legitimate chance to compete for a World Series title in the coming seasons. His dominance on the mound would complement their already talented lineup, and with the Cubs looking to make a deep postseason run, having a Cy Young winner on the roster would give them the edge they need.

Detroit’s Rebuilding Efforts

For the Tigers, moving Skubal might make sense if they can land a promising return that helps accelerate their rebuilding efforts. Matt Shaw, the Cubs’ rising star, is a versatile infielder with the potential to be a cornerstone of Detroit’s future. Shaw, alongside Wiggins and Conrad, would give the Tigers a strong package of young talent that could help them retool and build for the future.

The Tigers are looking for players who can make an immediate impact and help them in the near term, while also adding long-term assets to their roster. This trade could help them continue their rebuild with players like Shaw, who could eventually become a key contributor to the team in a few years.

The Bottom Line

As the Cubs continue to position themselves as contenders in the National League, acquiring Tarik Skubal would be the final piece of the puzzle. With his proven track record as a two-time Cy Young winner and his ability to dominate on the mound, Skubal would instantly elevate the Cubs’ pitching staff and make them a more complete team. If the Cubs can get this deal done, they would be ready to contend not just for the NL Central but for a World Series title.

But with the Tigers’ demands for a proven MLB-ready pitcher in return, the Cubs must be strategic in their approach. The clock is ticking, and the Cubs will need to act quickly if they hope to land one of the league’s most dominant pitchers before Spring Training begins.

Stay tuned for further updates as this blockbuster trade proposal continues to unfold, and whether the Cubs can pull off this move to strengthen their playoff aspirations.