If the goal is simply making the playoffs, the Chicago Cubs appear to have done enough to set themselves up for a successful 2025 season.
The offseason acquisition of Kyle Tucker, an MVP-caliber talent, bolsters a roster already featuring rising star Pete Crow-Armstrong and National League Rookie of the Year contender Matt Shaw. With this mix of proven and emerging talent, many predict the Cubs will finish atop the NL Central. While some still favor the Milwaukee Brewers to repeat as division champs and others see the Cincinnati Reds as a potential dark horse, the general consensus is that Chicago should win enough games to secure a postseason berth.
However, performing in October is a different challenge altogether. As spring training comes to a close, the odds aren’t particularly in the Cubs’ favor when it comes to making a deep playoff run. Despite six National League teams ultimately qualifying for the postseason, Chicago currently ranks seventh among NL teams in terms of their chances to win the World Series.
Adding Dylan Cease Would Give Cubs Another Ace Alongside Shota Imanaga
While the Cubs seem to have assembled a lineup capable of making a legitimate title push, questions still linger about their pitching staff—especially in the starting rotation. At the top, Chicago is anchored by two All-Stars in Shota Imanaga and Justin Steele, and they’re counting on veteran arms Jameson Taillon and Matthew Boyd—who signed a two-year deal earlier this offseason—to deliver consistent, quality innings.
However, the fifth spot in the rotation remains uncertain. How the Cubs address that gap could significantly impact their ability to compete with the elite pitching staffs of likely postseason contenders like the Los Angeles Dodgers, Philadelphia Phillies, and Atlanta Braves.
For many Cubs fans, the ideal solution would be a trade for a frontline ace. According to a Cubs Insider reporter, the team has the assets to put together a package that could land them a top-tier starter—someone capable of anchoring the rotation and giving Chicago a better shot at winning a playoff series.
Cubs Insider Report Suggests Trade Packages to Acquire Dylan Cease
With the possibility that the San Diego Padres could move Dylan Cease at some point this season, Michael Canter proposed two trade packages he believes might appeal to San Diego. The first offer includes Jordan Wicks, Kevin Alcántara, Jefferson Rojas, Jaxon Wiggins, and Brandon Birdsell. The second package would send Alcántara, Ben Brown, James Triantos, and Javier Assad to the Padres.
“I know that’s a hefty price, and I’m sure some readers will push back,” Canter acknowledged, “but lining up Cease alongside Justin Steele and Shōta Imanaga in a postseason series against the Dodgers—or any contender—gives the Cubs a real shot.”
There’s still uncertainty about whether Cease will even be available anytime soon. Many analysts think the Padres will let the regular season play out for a while before they seriously entertain offers for the 29-year-old, who has been one of MLB’s most reliable and durable starters over the past four years.
“He racks up strikeouts against some of the best hitters in the game, but his greatest asset is his durability—remarkable, really,” MLB insider Jon Heyman said. “How many pitchers lead the league in starts three times in four years? His value is massive, and I doubt the Padres will move him unless they get something that helps their roster right now. That’s tough, considering it’ll be contenders making offers.”
Reports suggest the Cubs are among nine teams that have already reached out to San Diego about Cease. Including arms like Assad, Brown, or Wicks could help meet the Padres’ need for immediate pitching help, but whether both sides can come to terms on a deal remains uncertain.
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