Kyle Tucker Trade Rumors Keep Swirling: Is Taking On Ryan Pressly a Win-Win Way to Bridge Gaps?

Although the reports are just confused and confusing enough to leave everyone bickering about the real nature of the demands, all indications are that the Astros want both Seiya Suzuki and Isaac Paredes in a trade for Kyle Tucker, whom the Cubs would then control for just one season before he hits free agency. Tucker might be worth those two, in an emerging paradigm of player value that disproportionately elevates stars at the expense of average-ish players, even though they're under team control for longer than he is and are solid contributors themselves.

Houston (understandably) also wants to get a longer-term benefit from giving up such a superb player in the short term, though, and that has led to a long negotiation. The Cubs don't want to give up Matt Shaw, or even Cam Smith, in exchange for Tucker, at least without holding onto one of Suzuki and Paredes. While one report Thursday night juiced a new round of speculation and excitement, the chances that these two teams are unable to bridge the divide and end up deciding not to do business together is still significant.

The path out of this encroaching stalemate could go through the Houston bullpen. Earlier this winter, multiple reports suggested that the team was looking to trade reliever Ryan Pressly, to whom they owe $14 million in the final year of his most recent contract extension. After Houston signed Josh Hader to a massive deal last winter, they have a surplus of talent in the bullpen, and with Bryan Abreu available to act as Hader's second in the relief wars, Pressly has gone from one of the game's elite closers to an expendable set-up man in short order.

Because he's owed so much and because he's declined somewhat sharply over the last two years, Pressly has negative trade value. To move him in a separate deal, Houston would have to attach a prospect or eat as much as $4 million. Pressly struck out 31.9% or more of his opposing batters every year from 2018-22, but that figure plummeted to 27.6% in 2023 and 23.8% in 2024. His velocity has similarly flagged, from an average fastball at 95.4 miles per hour as recently as 2021 to 93.8 MPH in 2024. That's not a great case for the Cubs acquiring him, of course. Still, it could help balance the scales.

With Tucker and Pressly going to Chicago and Paredes (but not Suzuki) going to Houston, the Astros would save something like $25 million for 2025. The Cubs would be taking on significant money, but they'd also have their lineup anchors in place, and they'd rebalance their books by trading Cody Bellinger—which they're treating as a prerequisite for acquiring Tucker, anyway. Meanwhile, bringing in Pressly would lighten the pressure to make any further additions to the bullpen, so it would effectively free up the money they would otherwise have had to earmark for that item on the to-do list. Under those circumstances, they'd probably be much more amenable to trading a top prospect—even if it be Shaw. Another structure could emerge, too, where the Cubs would send Owen Caissie, Cam Smith and Paredes to Houston, allowing them to retain Shaw and James Triantos with an eye to having one or both of them play third for the next several years.

To circle back to Pressly, despite the dipping velocity and strikeout rate, this isn't exactly a Héctor Neris situation. For one thing, Pressly has a deep arsenal. As he's aged, he's added a sinker and a changeup to that mix, which included an elite fastball, slider, and curve at his best. Now, according to pitch modeling ratings, the fastball has sagged badly, to about average—but the curve and slider are still among the best in the game, and the changeup he just found in his early 30s is turning out to be an average-plus offering. The smart money says that, despite losing his ability to overpower and befuddle hitters, he can still get them out at a solid rate.

If we assume the Cubs would go on, after this trade, to get Carson Kelly sewn up, we can loosely project a roster for 2025 based on the things we understand the team to be trying to do. 

Starting Lineup

1. Ian Happ - LF
2. Kyle Tucker - RF
3. Seiya Suzuki - DH
4. Michael Busch - 1B
5. Dansby Swanson - SS
6. Matt Shaw - 3B
7. Pete Crow-Armstrong - CF
8. Carson Kelly - C
9. Nico Hoerner - 2B

Bench

• Miguel Amaya - C
• Gage Workman - IF
• Alexander Canario - OF
• Miles Mastrobuoni - UTIL

Starting Rotation

1. Shota Imanaga
2. Justin Steele
3. Jameson Taillon
4. Matthew Boyd
5. Javier Assad

Bullpen

• Ryan Pressly
• Porter Hodge
• Tyson Miller
• Nate Pearson
• Eli Morgan
• Julian Merryweather
• Luke Little
• Daniel Palencia

This includes a trade of Cody Bellinger, but excludes any player received in exchange for him. It also leaves undreamt any dreams of adding another starter to the front end of the rotation, rather than to the back end (via the acquisition of Will Warren, perhaps). From this position, the Cubs could try to package more young talent (Kevin Alcántara, any of several strong pitchers just off the fringes of the MLB roster) or find a way to land Nico Hoerner in Seattle and get back Luis Castillo. The latter option would further risk the team's fortunes on the performance of young players, since Triantos would then need to come up and help the team almost right away.

Not quite a juggernaut, the team above would nonetheless be markedly higher-ceiling and more dynamic than the one the Cubs have now. It would have to be accomplished by accepting some suboptimal arrangements and stretching the team's expected 2025 budget near its breaking point, and there is always a very real risk that this front office will back off when faced with that set of choices. However, if bringing Pressly into a Tucker trade could keep Shaw and/or Suzuki out of it, the Cubs have to explore that possibility. One way or another, we're likely to know by the end of this weekend whether anything will come of all that big Winter Meetings week talk.