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Chicago Cubs: Prioritizing the trade deadline shopping list

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Chicago Cubs president of baseball operations Jed Hoyer talks to the media after introducing pitcher Shota Imanaga (not pictured) during a press conference at Loews Chicago Hotel.

The Chicago Cubs have needs.

In a perfect world, the Cubs’ potent and diversified offense would carry them through the rest of he season and deep into the postseason, making pitching concerns a non-issue.

The baseball world, however, is seldom a perfect world.

The Cubs walk into the last part of May still in first place and riding high on a wave of enthusiasm.

They also have to face the reality that their bullpen is wildly inconsistent in spots and lacking a true shutdown closer. Offseason acquisition Ryan Pressly has not been that guy and backup Porter Hodge now finds himself on the IL.

Meanwhile, the starting rotation also finds itself in a precarious spot, with three of the projected top 5 starters out of commission. Ace Justin Steele is lost for the year after elbow surgery. Co-ace Shota Imanaga is dealing with a tricky hamstring injury with no clear return date in sight. Javier Assad is out until mid-season with lingering oblique issues.

Free agent pickups Matthew Boyd and Colin Rea have been valuable assets, but the Cubs need more. A starting rotation with the inconsistent Jameson Taillon, Ben Brown, and rookie Cade Horton having such prominent roles is not one capable of taking the team deep into the playoffs.

So, it’s obvious that the Cubs will have to bring in some assets via trade.

More Urgent For The Chicago Cubs: Bullpen Or Starting Rotation?

Chicago Cubs pitcher Ryan Pressly (55) throws a pitch during the ninth inning against the Athletics at Sutter Health Park.
Chicago Cubs pitcher Ryan Pressly (55) throws a pitch during the ninth inning against the Athletics at Sutter Health Park. Mandatory Credit: Ed Szczepanski-Imagn Images

But which need do they address first and, given the limit to available trade capital, how much of their future do they deal away for a chance to win right now?

On a recent edition of the Baseball Today podcast, former Minnesota Twins infielder Trevor Plouffe, stated his belief that the bullpen is not the team’s most pressing concern right now

“I don’t think it’s pressing that they need to do it right now,” Plouffe said. “You need to see what you have in some of these guys. Like, Palencia has the stuff to be a closer. He just needs to locate a little better.

“Right now, you can look at some of these guys and say, ‘Okay, can we trust you in high-leverage spots?’ Sure, do they want to add their bullpen eventually? Yes, I think so, but I don’t feel it’s super pressing right now. I’d actually look at some of these guys and see what we have. And if it doesn’t turn out, maybe yeah, go make a move.”

Decisions, Decisions

Chicago Cubs, Daniel Palencia
Daniel Palencia (48) reacts after getting the final out on Arizona Diamondbacks shortstop Geraldo Perdomo (2) against the Arizona Diamondbacks during the ninth inning at Wrigley Field. Mandatory Credit: David Banks-Imagn Images

Despite lacking a shutdown closer, there have been some reasons for optimism when it comes to the bullpen. Brad Keller, Caleb Thielbar, Drew Pomeranz, Tom Cosgrove, Chris Flexen, and Daniel Palencia make up a ragtag relief corps, but they’ve been getting the job done. Palencia, despite the poor outing the last time out, has shown signs of having closer stuff with a closer’s mindset. Even Pressly, after that disastrous 8-earned-run appearance earlier in the month, hasn’t allowed an earned run in his five subsequent outings.

So, maybe, the focus should be on starting pitching?

Or, what if Matt Shaw doesn’t pan out in this second try at the majors? Will they also need to pursue a dependable third baseman?

There’s no easy answer when it comes to who the Cubs will target in a mid-season trade.

They’ll Have To Wait

MLB: Miami Marlins at Chicago Cubs, Jed Hoyer
MLB: Miami Marlins at Chicago Cubs

“Who” is still a very open question and one which won’t see an answer until late next month at the earliest.

“Thinking about big external transactions, that’s really at least a month away, if not more. I think we got to focus on smaller transactions and we got to focus on getting healthy,” Cubs president of baseball operations Jed Hoyer recently said in an appearance at Chicago radio station 670 The Score.

No matter what issue(s) they decide to address, they’ll have to wait until teams make their trade-worthy assets available. Big deals are unlikely in May or early June. Then, they’ll have to decide on how much of their future they’re willing to mortgage so they can try and win right now.

The best bet is that the Cubs will focus on starting pitching, giving up at least a couple of their top prospects to add a reliable front-of-rotation starter. From there, they could likely pull off a couple of smaller deals for bullpen arms, while possibly moving Brown to the pen as well, with Imanaga, Assad, and their new trade acquisition hopefully fortifying the rotation, alongside Boyd and Rea

As is always the case, time will tell.


Source: https://www.chicitysports.com/chicago-cubs-trade-targets-2025-deadline?utm_source=rss&utm_medium=rss&utm_campaign=chicago-cubs-trade-targets-2025-deadline


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