The San Diego Padres could obtain an excellent group of young players from the Chicago Cubs if they decide to trade Dylan Cease this month.

It is MLB trade season, and the San Diego Padres could be front and center in several different ways.

Most suggest that the Padres will solely acquire players this July, but there are already reports that the team may take a different approach.

Jon Heyman of the New York Times is reporting that the Padres are listening to offers on Dylan Cease. He mentions both New York teams, the Cubs, and the Red Sox as possible suitors.

Trading Cease may seem unusual for MLB fans, given that the Padres are contending and certainly lack depth in their starting pitching department. However, the Padres are well aware that Cease, who is a pending free agent, will not return to San Diego in 2026. His asking price will certainly be too much for the Padres.

It may be wise to trade the pitcher now. The Padres are certainly exploring that option.

The Chicago Cubs make sense on several levels.

Dylan Cease would strengthen their starting staff and provide a player who could eat innings down the stretch. Cease would be a rental, and the Cubs are still very much in contention, so they would not trade any of their young players currently on the roster. The deal would likely involve prospects.

San Diego will need to have a backup plan in trading Cease regarding the starting staff. Yu Darvish and Michael King are returning from injury, but both pitchers are still iffy to remain healthy for the rest of the season. A trade of Dylan Cease may seem risky, but if San Diego can secure a backup plan somewhere, then it could be viable.

Can the Padres add another arm or two to replace Cease and do it on a budget? We will see.

As far as the Cubs, Chicago has an interesting outfield prospect who the Padres are familiar with. Owen Caissie was drafted by the Padres in the second round of the 2020 MLB Draft out of a high school in Canada. San Diego traded Caissie with three prospects and Zach Davies to the Chicago Cubs for Yu Darvish just months after he was drafted.

The left-handed hitting outfielder is in Triple-A and is seasoned for major league service time. The 23-year-old is putting up a .960 OPS with 20 homers in his second season in the International League. With the Cubs focused on re-signing Kyle Tucker this winter, Caissie is deemed expendable at this point. Chicago has a very good chance of retaining Tucker, and most deem Caissie a strong trade chip this July.

Caissie alone may be attractive enough for the Padres, but Moises Ballesteros would also be a player worth checking in on. The left-handed hitting catcher is currently in Triple-A, where he owns a .884 OPS in 81 games. He spent some time at the major league level this season, but has no real chance at constant playing time. Ballesteros is an excellent hitter despite his small stature (5-foot-8). The 21-year-old owns a. 290 career average in over 1,500 minor league at-bats.

Ballesteros is not a solid defender, so it remains to be seen if he can further develop at the position. But the Padres need offense. Teaming Ballesteros with a right-handed hitting defensive catcher may be the best move for the team moving forward.

One way or another, it seems like Dylan Cease will be traded. If it happens, the Chicago Cubs are a strong candidate.

James Clark

James was born and raised in America’s Finest City. He is a passionate baseball fan with even more passion towards his hometown Padres. James has written about the Padres and their prospects for over a decade. He also writes about San Diego State as well as other local sports. James is the Editor-In-Chief of EastVillageTimes.com. Always striving to bring you the highest quality in San Diego Sports News. Original content, with original ideas, that’s our motto. Enjoy.