Chicago Cubs: What a Dylan Cease trade with the San Diego Padres would look like

The Chicago Cubs, despite having already had a productive and meaningful offseason, appear to be still on the hunt for some additional talent to add to the opening day roster.

Uncharacteristic of the franchise and its front office, the team has been aggressive this winter, unsuccessfully pursuing free agent closer Tanner Scott and, reportedly still pursuing, third baseman Alex Bregman. They’ve also been willing to trade well-regarded prospects for high-end, field-ready talent.

Notably, their deal for Houston Astros all-star right fielder Kyle Tucker was a supreme shocker, costing them top prospect Cam Smith, pitcher Hayden Wesneski, and third baseman Isaac Paredes for the one-year rental of the multi-tool asset.

Chicago Cubs In Pursuit Of Dylan Cease?

The latest buzz has Jed Hoyer and his team exploring the possibly of a trade for San Diego Padres ace Dylan Cease, who was brought up in the Cubs farm system.

There are plenty of questions asked of a Cease deal, however. For instance, how much would it cost the Cubs and, consequently, would it be worth the price for a player who, like Tucker, will become a free agent at the end of this coming season.

Questions To Be Asked

Matt Cozzi and Sam Olbur of the Locked on Cubs podcast mulled over this dilemma in a recent episode of their show and offered up some considerable food for thought, as well as an idea of what such a Cubs-Padres trade would look like.

Per Cozzi:

“They have their own trade from a month ago as a possible format…It would be a combo platter here of three players. One is a major league starting position player or pitcher. One’s a top prospect. And then a third piece who’s in limbo or blocked with the Cubs, but offers major league value of some sort on day one with the team. And that was the Astros trade.

So, here’s what it would be this time.

I think it would be either [Javier] Assad or [Jordan] Wicks because they immediately go into the rotation, either [Kevin] Alcantara or [Owen] Caissie, and a third player, someone of the ilk of Wesneski…”

Cozzi would then bring up the big question of whether that’s too much to give up in a second major deal for a rental player this season.

Risk vs. Reward

His co-host would follow up with the only possible response– it depends on how much the organization values winning in the moment.

Per Olbur:

“If you really want to get into the nuance of it, it’s how much do you value winning the division. If you trade Owen Caissie, and you already traded Cam Smith, for Tucker and Cease and you win 91 baseball games, you win the division, but you lose that three-game series at Wrigley Field to start the postseason…is it a successful season? Was it worth trading those prospects?”

There’s definitely a lot to think about when it comes to pulling the trigger on a trade like this. Cozzi mentions it as almost an ethical dilemma for Hoyer, as he enters this final year of his contract with the Cubs. Is it right to deplete his team’s farm system in pursuit of a contract extension via winning 2025 campaign (or as he walks out the door, possibly headed to another team)?

The Cubs adding Cease should all but guarantee a postseason run this year, but does winning now trump the slow build– and risk– of trying to establish a long-term winning organization?