At MLB Trade Deadline: Can Cubs Pillage Pirates for All Their Needs (Again)?

[RandallPnkFloyd]

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While my memory of the more specific context is a little spotty for someone who was 13 years old at the time, the impact of the Chicago Cubs' 2003 trade with the Pittsburgh Pirates is anything but. 

That year, the Cubs shored up what then-GM Jim Hendry believed to be a playoff-caliber roster by acquiring third baseman Aramis Ramírez and Kenny Lofton for a relatively unimpactful package that included infielder José Hernández off their active roster. Lofton was a journeyman leadoff man who fit perfectly into a Corey Patterson-less roster, while Ramírez was a bounceback candidate (after a rough 2002) who ended up becoming one of the more important Cubs in modern history. 

The deal, of course, propelled the Cubs into the postseason. Ramírez came up with several clutch hits to push them deeper into October, and that would be his habit for most of the next decade. Now sitting 22 years clear of such a one-sided deal, could the Cubs and Pirates align on another landmark transaction? 

The Cubs' needs at this point are clear. Starting pitching tops the listt. A bat (of the impending free-agent variety) has jumped the line to just behind said starting pitcher, given Matt Shaw's underwhelming offensive output at third base, even if he has been better since his return from Iowa. Some help off the bench would be nice, too. Like any playoff hopeful, they'll also try to upgrade their bullpen.

That brings us to the Pittsburgh Pirates. The Bucs are, objectively, bad. Their pitching and defense can make life difficult for contenders as the season wears on, and they've done some of the Cubs' dirty work by beating up the Mets and Cardinals over the last week, but at 37-50, they're one of the few clear-cut sellers here in July. They're 14 games behind the Cubs and 10 games out of a Wild Card spot.

Given the Cubs' desire to act on their needs within a more immediate timeline, it's only natural that the two teams would be connected in trade talks. We've already heard the rumor that the Cubs are targeting starter Mitch Keller. On the Pirates' end, the context of their season thus far has them listening on just about everybody. Before this is all said and done, we could hear about far more than Keller as it relates to the Cubs and their July trade targets.

"Just about everybody" is an important qualifier in all of this. Paul Skenes isn't likely to be moved, and while Andrew McCutchen would be a sort of ideal target in a Justin Turner-type role (without the first-base acumen), he appears set on playing out what's left of his career in the Steel City. So those two—along with a top pitching prospect like Bubba Chandler or an injured one like Jared Jones—are out. That still leaves plenty of room for the Cubs to strike a deal that fills multiple needs, however.

The framework starts with Keller, a logical trade target given that he:

1. is a starting pitcher; and
2. carries a certain level of cost certainty on a contract that runs through 2028.

Keller has never fully realized his potential in Pittsburgh, but he's turning in a solid season for the Pirates. Even with a strikeout decline, he's pitched to a 3.90 ERA, a 3.33 FIP, and is averaging 5.8 innings per start thus far. That's exactly the type of arm that the Cubs could use: someone who offers a little bit of stability in between what you're getting out of a young arm and Jameson Taillon's propensity for the occasional clunker of an outing. 

But the Cubs have an opportunity here to extend beyond only their largest need. Andrew Heaney is a shorter-term commitment on a one-year deal, but he provides a similar level of length (5.5 innings per outing) with steadiness reflected in his 4.20 ERA over the last three years. There isn't as much upside here, but the term is favorable and he'll eat some innings in the back end of the rotation. In an ideal world, you're getting a Keller type with the upside and a Heaney type with the stability. We, of course, don't live in that type of world, but either one represents a sensible target, nonetheless. 

Meanwhile, David Bednar has been excellent after yet another early-season demotion. He's pitched to a 2.93 ERA, and the 35.3% strikeout rate is a career-best. If you remove pre-April 19th, things get even better; the K-rate jumps to 37.4% and the ERA shrinks to 1.95. Similarly, Dennis Santana has worked to a 1.50 ERA (2.39 FIP) in a predominantly late-inning role. If the Cubs are trying to shore up the end of games, either would represent a fantastic get, with each having a year and a half of team control remaining.

"But what about the bats?" you might be asking. McCutchen would certainly be a big right-handed upgrade to the bench if he was, in fact, willing to join a contender for a couple of months, but we don't know what that looks like. We've heard some whispers about Ke'Bryan Hayes' availability, but he doesn't offer much of a bump in the lineup, and the commitment is such that you're pivoting to a block of Matt Shaw (club option in 2030). Isiah Kiner-Falefa, though, offers a bit better of a hit tool with an experienced glove (27 Outs Above Average in his career at third base). In pursuit of depth, he's a logical target.

Ultimately, though, the Cubs may have to look elsewhere for their offensive pursuits. If McCutchen is indeed committed to staying, options are few and far between. You've nowhere to put Oneil Cruz, nowhere to put Bryan Reynolds, and no chance of prying either of them away from Pittsburgh, anyway. Outside of the couple of infielders noted above, there just isn't enough upside to complicate a potential deal by trying to shoehorn a position player in as well. 

A starter-starter or starter-reliever combination would yield crucial components of a potential postseason roster. There's just one other complication: an in-division opponent. 

That doesn't feel like as much of a hurdle between these two clubs as it would be between, say, the Cubs and the Milwaukee Brewers or the Cubs and the St. Louis Cardinals. By my count, these two clubs have consummated roughly 50 trades of varying natures in their respective histories. Not all of them have carried the weight of 2003's, but there are certainly deals where the Pirates have included important contributors. The 2009 season comes to mind, when John Grabow and Tom Gorzelanny were sent to the North Side in a deal that included Josh Harrison (yes, that one) and Kevin Hart (no, not that one). 

So there's a little bit more of a precedent here between the Cubs and Pirates that doesn't exist with other in-division rivals. Besides, Jed Hoyer and Pirates GM Ben Cherington are old mates from their Boston days. That divisional component presents as less of a factor, given such historical dynamics between executives and organizations.

The two are kind of a natural fit for a trade. The Cubs have their very obvious needs; the Pirates are a seller without a lot of direction, making most of their roster available. It's difficult to pinpoint the exact intricacies of a trade could look like, but there's a match here.

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