The MLB 2024-25 off-season has been busy for many big-market teams, including the Chicago Cubs, who have made two of the biggest trades across the league this winter.

First, they acquired All-Star right fielder Kyle Tucker from the Houston Astros for third baseman Isaac Paredes, RHP Hayden Wesneski, and RHP Cam Smith on Friday. On Tuesday afternoon, the Cubs sent OF/1B Cody Bellinger and $25 million of his $27.5 million salary for 2025 to the New York Yankees for 30-year-old RHP Cody Poteet.

The Cubs trading Bellinger to New York only cost them the $5 million they owe him between 2025 and 2026. Half the money goes toward each season’s salary, or he can opt-out if he chooses free agency again in 2026. With $25 million now freed up to spend, the Cubs have a lot to work with either by adding depth through free agency or trades.

That’s where the Minnesota Twins may come in to offer veteran MLB talent the Cubs still need on their roster to compete in 2025. Before the Cubs signed catcher Carson Kelly the same day they acquired Tucker, the Cubs looked like one of Minnesota’s more likely trade partners to make a deal for fellow catcher Christian Vázquez.

Chicago needs pitching depth. It may be more for the bullpen than the rotation, but given some of the history of injuries their starters have had, it may not be a bad idea to get one more, which is where Chris Paddack comes in.

The Cubs have already discovered how expensive the free agent market is even for back-of-the-rotation starting pitchers when they signed LHP Matthew Boyd to a two-year, $29 million deal on December 2. Boyd didn’t have a bad season in 2024. He only made eight starts for the Cleveland Guardians down the stretch and threw 39 ⅔ innings, posting a 2.72 ERA, a 1.13 WHIP, and struck out 27.7% of batters he faced.

However, Cleveland didn’t sign him until June 29 to a minor league deal because he hadn’t pitched since June 26, 2023, after undergoing Tommy John surgery. Between his five minor league rehab starts and eight starts with Cleveland, Boyd only pitched 61 ⅓ innings in 2024, which was 27 fewer innings than Paddack had.

Paddack also wasn’t healthy in 2024. He was returning from a second Tommy John surgery that hindered his time on the mound with the Twins. There were still the occasional dominant starts from him, such as his start against the Guardians on May 19, where he allowed only two runs in eight innings and didn’t walk anybody.

Paddack’s injury history and mixed results in 17 starts with the Twins last season may make him harder to move. Still, he is only making half the amount of money in 2025, and Boyd is at $7.5 million, so he’s less of an injury risk. They could be viable options for the Cubs to split time in the fifth rotation spot as needed.

Adding Paddack alone for the Cubs would also leave them $17.5 million to spend elsewhere from the salary freed from trading Bellinger. So, which Cubs player should the Twins target?

Fortunately for the Twins, the Cubs have a slight excess of right-handed hitting outfielders that could help provide depth behind Byron Buxton, Matt Wallner, and Trevor Laranch. Kevin Alcántara would be the ideal fit. He’s a 22-year-old right-handed hitting outfielder who can play all three outfield positions.

Alcántara made his MLB debut with the Cubs on September 25, 2024, and played in only three games before the season ended. Still, MLB Pipeline ranks him sixth in Chicago’s system and 67 overall on MLB Pipeline’s top 100 prospect list. They give him 50 or 55 with his tools (hit, power, run, field, etc.) on the 80-20 scale, around the average for an MLB-ready prospect.

What’s kept Alcántara from getting more major-league opportunities if he’s close to  MLB-ready? The Cubs still have a crowded outfield, and Alcántara is not high on their depth chart.

The starting positions are locked in by Tucker, Ian Happ, and Pete Crow-Armstrong, with Seiya Suzuki expected to split time in right fielder with Tucker. Fellow outfield prospect Owen Caissie is listed as Chicago’s second-best prospect and 34 overall by MLB Pipeline. The Cubs also recently graduated prospect Alexander Canario, who has only played 21 games in the majors. He looks primed for more consistent playing time as Chicago’s fourth outfielder this season.

The Cubs have more outfielders than they know what to do with. The Twins may be looking that way soon with their starting rotation options waiting in the wings at Triple-A. By trading for Alcántara, he would become Minnesota’s fourth-best prospect by default and get more playing time. Paddack could get more time as a starter in Chicago than with the Twins next year.

The swap for these two players alone may make sense on paper. However, given Alcántara’s prospect status, he will draw a larger return price tag. Last off-season, the Baltimore Orioles traded the only top-100 prospects from MLB Pipeline’s list when they sent  DL Hall and Joey Ortiz to the Milwaukee Brewers from the Orioles for Corbin Burnes. Since then, no top 100 prospects from any major publications list (Baseball America, Pipeline, or Baseball Prospectus) have been traded.

Alcántara and Cassie look like two of the more likely top 100 prospects to be moved before Spring Training. However, given the scarcity of teams willing to move the top talent for their organization’s future, this will come at a higher price than some teams may want to pay.

If Paddack for Alcántara can’t get the deal done alone, who or what else can Minnesota include for compensation? The Twins could trade their competitive balance draft pick with Paddack to entice the Cubs to let go of Alcántara. The Cubs didn’t get a competitive draft pick this off-season.

Suppose the Cubs want players and not a draft pick. Then, Jorge Alcalá could be another option for the Twins to include because Chicago still needs bullpen depth. Suppose they want another outfielder for the future. Then they could include Gabriel Gonzalez, who the Twins acquired from the Seattle Mariners in the Jorge Polanco trade last off-season, to balance things out.

The Twins and the Cubs have an opportunity to help each of their rosters out with a better chance to compete for the postseason in 2025. If they can both find a way to make an Alcántara for Paddack deal work, it would be one of the best ways they can move Paddack.