5 Trades the Chicago Cubs should make as buyers at the MLB Trade Deadline

A little over a month ago I posted an article that did a deep dive on five prospect packages the Chicago Cubs should be excited to get if they’re sellers at the trade deadline.

What a difference a month can make because since that time the Cubs are 14-8 and are only 3.5 games out of first place. That means that we are now going to look at some potential trades the Cubs could make at the deadline if they continue on this trajectory and look like buyers.

This is not going to be an article that has the Cubs receiving the top available players in the trade market in return for bottom-of-the-barrel prospects. You’ve got to give in order to get in this league. We won’t see any trades within the division regardless of how bad the Cardinals are because it is exceedingly rare. The idea here was to focus on a couple of things:

1. What are areas of need on this Cubs team that could continue to be areas of need moving forward into the contention window? 
2. Are there teams that will be sellers that have players that could fill those areas of need, and moreover are the players that they could make available controllable for more than this season?
3. What is a reasonable return based on the status of the team that the Cubs trade with? For example, a trade with the Giants may see the Cubs send prospects that are closer to the majors, whereas a team like Colorado may be looking for younger, higher-upside players.

With that being said, here are five trades that the Cubs should be ecstatic to complete if they are able to continue winning and find themselves in a playoff race in July and August.

Trade 1: The Chicago Cubs receive RHP Daniel Bard and LHP Brad Hand from the Colorado Rockies in return for INF Pedro Ramirez and RHP Ryan Jensen

This is the kind of trade that teams make around the deadline every year, they find a way to improve the bullpen and then they find a team that isn’t really in need of theirs and they poach them. It’s a little more rare to see two relievers get sent in the same deal but with the package the Cubs are offering it’s not out of the realm of possibilities to try to get two guys instead of one. 

Daniel Bard has been dominant this season. He’s got a 0.79 ERA and the Cubs would have him locked up for the rest of this year as well as next season at $9.5 million per year. 

The other piece they’d get would give them a lefty out of the pen that they sorely need in the form of Brad Hand. He hasn’t been as good as Bard this year and even though he’s significantly more cost-efficient at $2 million, he’d surely be a rental for the remainder of the season.

If the Cubs don’t love the idea of taking on an additional $11.5 million this year then they could likely get the Rockies to eat a little bit of the money if they were willing to upgrade Ryan Jensen to someone like LHP DJ Herz.

The Cubs aren’t getting out of this thing by giving up anything. Ryan Jensen has struggled for much of his career since being a first-round pick in 2019, but he finds himself in AAA right now as a legitimate late-inning relief option if he can ever figure out how to limit the walks. If I were in the Rockies organization my goal would be to get pitchers that qualify contact and Jensen is that kind of player.

Along with Jensen, the Cubs would send teenage middle infielder, Pedro Ramirez, who was excellent in Rookie Ball last year with a .329/.399/.541 slash line and has been fine in Myrtle Beach this year playing at nearly two years younger than his average competition. 

This deal isn’t one that will make or break either team, but it’s one that gives both sides a win for the direction they’re headed. The Rockies get a top-30 player and a top-20 player from the Cubs system and the Cubs gain two more arms out of the bullpen that they can trust later this season.

Trade 3: The Chicago Cubs receive OF Brent Rooker from the Oakland A’s in return for INF Jared Young and RHP Caleb Kilian

The Oakland A’s (soon to be Vegas Aces I’m sure), are truly terrible. Even with their recent winning streak and moderate attendance to their reverse boycott, they are still historically bad. They will be looking to sell at the deadline, but aside from Brent Rooker they legitimately might not have a piece worth buying. 

For my money, this may be the most interesting trade on the list. Rooker is under team control through 2027 which is his age-32 season. He’s a corner outfielder and the Cubs have their corners locked up between Ian Happ and Seiya Suzuki, but Rooker’s calling card is his bat and it’s good enough to allow him to DH on a playoff team. 

Much like Candelario, if Rooker could hit left-handed this one would be a no-brainer for the Cubs as he has hit .250/.350/.482 this season with 13 homers and 12 doubles on an offense that can’t protect his bat. If he could get into a lineup where he’s surrounded by players like Suzuki, Happ, Hoerner, Bellinger, and Swanson then he should see even better pitches that he can do more damage with. 

The cost for such a player is significantly higher than the cost for someone like Candelario. The Cubs would be forced to deal a pitcher that they received as the main piece in the Kris Bryant deal a few years ago. Caleb Kilian has already made his major league debut and while David Ross said that he was “not ready,” he would likely represent the second or third-best starter for Oakland right now. 

Beyond that the Cubs would send Jared Young who is the exact kind of player that Oakland always manages to turn into an All-Star. He’s dominating AAA this year to the tune of .320/.433/.567 and he’s played first base and the corner outfield positions so far this year. He doesn’t currently find himself in the top 30 in the system, but somehow I imagine Billy Beane doesn’t care much about MLB.com’s prospect lists. 

I don’t know why The A’s would look to deal Rooker. He’s cheap, he’s relatively young, and he’s a solid player which is exactly what they covet. That being said, this package would be competitive as the Cubs would send their 17th best prospect and a hitter that could slot into their lineup today.

Trade 4: The Chicago Cubs receive LHP Eduardo Rodriguez from the Detroit Tigers in return for OF Kevin Alcantara, INF Kevin Made and RHP Porter Hodge

This would be an instance of the Cubs thinking outside the box. As the rotation is currently assembled it is an absolute strength: Marcus Stroman may be the best pitcher in the league, Justin Steele was dominant prior to his injury, the Professor Kyle Hendricks has returned with a vengeance, Drew Smyly nearly threw a perfect game against the Dodgers and Jameson Taillon was this offseason’s prized acquisition.

Beyond that, the Cubs have Ben Brown champing at the bit for an opportunity to pitch in Wrigley this season as well as depth options in the form of Hayden Wesneski and the aforementioned Caleb Kilian. 

So why deal for another starter, especially another left-handed starter for a team whose rotation already has two lefty starters? The honest answer is that I don’t believe that Smyly or Taillon can be counted on in a seven-game playoff series. 

This team is built around pitching and defense. In the playoffs, the strike zone tends to expand a little bit and contact hitting is extremely valuable and the Cubs seem to have the pieces in place to take advantage of that. However, after Stroman and Steele things get dicey when it comes time to put your proverbial boot on the opposition’s throat and Rodriguez would help solve that.

He’s under contract through the remainder of the season and has an opt-out after this year that makes things a little murkier. If he opts in he’d be making just over $16 million per year for the next three years, which may preclude the Cubs from offering an extension to Marcus Stroman, but he wouldn’t be a terrible consolation prize as he has a 2.11 ERA on the year so far. 

The other thing this deal would do is provide the Cubs the ability to get creative with the construction of the playoff bullpen. Does Taillon get right if he can shorten his appearances? Can Smyly be the left-handed reliever that the Cubs just don’t seem to have?

Unfortunately, trading for an ace like this is expensive and we wouldn’t be able to escape with trading prospects outside of the system top-ten. The Tigers would likely be looking for OF Pete Crow-Armstrong which the Cubs would have to deny. Teams make major deals like this all the time without including their top pieces and the Cubs have depth in the system that should allow them to deal a really good prospect without dealing their best prospect. 

Kevin Alcantara would be the prize in this deal but the Tigers would also receive two extremely solid additional pieces in the form of Made and Hodge. Made was a major international signing out of the Dominican Republic and Hodge is a piece that will likely end up in the bullpen long-term but is still being developed as a starter in AA right now. 

The Tigers may get better offers than this, but the Cubs don’t need a starting pitcher and so they shouldn’t overpay for one. If they can deal two (potentially) great prospects that are years away and a pitcher with relief concerns for one of the best pitchers on the market then you jump at it, but if the Tigers demand PCA they’ve got to walk away. 

Trade 5: The Chicago Cubs receive RHP Alex Lange and LHP Chasen Shreve from the Detroit Tigers in return for OF Brennen Davis and OF Yonathan Perlaza

This trade would cause me physical pain. Yonathan Perlaza has been one of my favorite Cubs’ prospects this season and Brennen Davis has been one of my favorite prospects over the past several seasons. That being said, when you have the ability to get a left-handed reliever and a high-leverage reliever with team control through 2027 you’ve got to give it a shot.

Alex Lange would be the crown jewel of this deal and he’s going to be tough to get, potentially even tougher than Eduardo Rodriguez given his extensive cheap team control. Chasen Shreve is a solid additional piece as well though. He’s the kind of player that good playoff teams have if he can get hot at the right time. 

When the Tigers traded for Alex Lange from the Cubs they dealt a half-season of Nick Castellanos. In order to get Alex Lange back as well as an additional half-season from a lefty like Shreve, the Cubs have to come up with a package of players that will pique the Tigers' interest.

Yonathan Perlaza is a major league-caliber player right now. He’s batting .295/.397/.537 with 29 extra-base hits and eight stolen bases. The question the Tigers will have to ask themselves in order to determine if this is the right deal for them is: can they fix Brennen Davis? 

There’s always a player that gets dealt at the deadline that is marketed as a “change of scenery” player. That doesn’t feel right in Davis’s case. He’s not a player that the organization has soured on. He’s not a player like Chris Davis with the Rangers where he’d mash in AAA but struggle in Arlington before getting dealt to the Orioles and going on a tear. He’s just dealt with some career-altering injuries.

If the Tigers look at the current production of Perlaza and the potential production of a former top-50 prospect in all of baseball as a fair return for two relievers then the Cubs have the ability to improve their team significantly in the immediate and near-term future with this deal. 

I don’t see a world where the Cubs complete all five of these deals (or even just two of them if I’m being honest with myself). That being said, these deals have the ability to improve the team immediately and in the near-term while not completely mortgaging the future. The turnaround from last month to this month was spectacular but hopefully, we won’t be writing an article next month about the Cubs selling at the deadline.

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