Chicago Cubs: Five players the team 'should' pursue this offseason

1 of 6

CHICAGO, IL – APRIL 12: President Theo Epstein of the Chicago Cubs waves to the crowd during a World Series Championship ring ceremony before a game against the Los Angeles Dodgers at Wrigley Field on April 12, 2017 in Chicago, Illinois. (Photo by Jonathan Daniel/Getty Images) /

The Chicago Cubs have some weak spots to fix before the start of the 2018 season. The free agent market isn’t particularly strong, so they may need to make some trades.

NOTE: This entire post is made in jest. It is a testament to the quality of players Theo Epstein’s front office has compiled on the current Cubs’ roster. Look at these names and reflect on how far the organization has come in the last five years.

The Chicago Cubs struggled for extended periods of time during the regular season. They were still the best team in the National League Central, but as we learned from their postseason appearance, what they had wasn’t quite enough.

When the Cubs were thwarted by the Los Angeles Dodgers in the NLCS, the clock struck midnight on their Cinderella story. As Cotton McKnight would agree, the Cubs had turned into the “proverbial pumpkin.”

So it’s time for Theo Epstein and Jed Hoyer to wave their magic wands and make the Cubs champions again (they should put that slogan on a hat). Have faith in the front office. They’ll make all your wildest dreams come true. You just need to tweet at the Cubs a list of players you want on the team. Then, like a sweatshop of Christmas elves, the front office works tirelessly to cross every player off your list. This is the process. Trust me, I’m a baseball blogger, so I basically know exactly how it works.

With that in mind, I’ve compiled a list of five players the Cubs should trade for this winter. They’ll win if, and only if, they acquire all five of them. Otherwise they’re doomed to fail. The customer is always right. Here we go.

SAN DIEGO, CA – SEPTEMBER 7: Clayton Richard /

5. Clayton Richard

With the likely departure of both John Lackey and Jake Arrieta, the Chicago Cubs have some holes to fill in their rotation. Clayton Richard is the obvious solution. He’s only 34 years old, so he could potentially be a long-term answer as well.

Richard has been one of the San Diego Padres‘ best pitchers the last the couple seasons, which is quite impressive when you consider the plethora of quality arms residing in their rotation. Over the course of 53 2/3 innings pitched with San Diego in 2016, Richard posted a 2.52 ERA with a whopping 34 strikeouts.

Can he handle the pressures of the postseason, you ask? Well, Richard has a career 0.82 ERA in the postseason, so yes, he’s your man if you want to start winning October baseball again. By comparison, Clayton Kershaw has a career 4.40 postseason ERA, so it’s safe to say Richard is the best “Clayton” in Major League Baseball. Sorry for that hard truth bomb.

Numbers don’t lie. Clayton Richard is a straight baller and the Cubs need him. What will it cost to get Clayton Richard? It won’t be cheap, but I think a package centered around Kyle Schwarber could get the job done. Clayton Richard briefly played football for the University of Michigan. Kyle Schwarber is bad at running. You do the math.

TORONTO, ON – SEPTEMBER 11: Darwin Barney /

4. Darwin Barney

The Chicago Cubs’ infield ineptitude stems from a lack of experience. Addison Russell, Javier Baez and Ian Happ are simply too young. If the team wants to get serious and end their miserable one-year championship drought, they need to add a veteran infielder into the mix. Enter Darwin Barney.

Barney is one of the few players in baseball history who can play both shortstop and second base. He currently plays for the Toronto Blue Jays of the Canadian Baseball League (CBL). I don’t know if trading across different leagues is permitted, but the Cubs should definitely try regardless.

Russell’s .240 career batting average is actually less than average. Barney’s .304 batting average in 23 at-bats in 2015 is very good. Had the Cubs traded for Barney earlier, they’d most likely be in the World Series right now. Instead it’s the Dodgers. And Barney used to play for the Dodgers before bolting for the CBL. Coincidence?

Ian Happ? More like Ian not Happ-ening, am I right? Barney played in 14 more games than Happ in 2017, so he has the necessary endurance to put the team on his back. He possesses superior power as well. Barney has 31 career home runs, while Ian Happ has just 24. This isn’t a difficult choice, you guys.

If the Cubs can get away with giving up just Russell and Happ for Barney, they’d be fools not to go through with it. The Blue Jays will likely want more, but the Cubs can probably afford to swing it.

MILWAUKEE, WI – SEPTEMBER 27: Matt Garza /

3. Matt Garza

Let’s get back to the rotation. Clayton Richard will undoubtedly provide a huge boost for the Cubs, but they shouldn’t stop there. They’ll still need a couple more ace-caliber starting pitchers. Look no further than Matt Garza.

By trading for Garza, the Cubs would not only be solving some of their rotation problems, they’d also be taking one of the best pitchers in the league away from division foe, the Milwaukee Brewers. With 12 years of MLB experience under his belt, Garza is an iron horse. It would be in the Cubs’ best interest to ride this bucking bronco back to promised land. He even comes with a full Kato Kaelin endorsement.

More from Cubbies Crib

Garza has previously played with the Tampa Bay Rays, managed at the time by Joe Maddon, who’s basically the Fonzie of baseball managers. So Garza would fit right in.

Like Clayton Richard, Garza also owns a better postseason ERA than Clayton Kershaw. Are you noticing a pattern here? That Kershaw guy is overrated and over-hyped.

I won’t bore you with the numbers. Matt Garza gets the job done. This mighty pitching beast has a colossal 93 wins to his name. The Cubs only won 92 games in 2017, so adding Garza would give them that extra push over the cliff. This only makes sense.

The Cubs would almost certainly have to give up a Javier Baez-caliber player if they wanted to make a run at getting Garza. But that’s the price you have to pay if you want top-tier starting pitching in this league.

2. Mike Olt

I’ll say what everyone else is too afraid to admit: Kris Bryant took a big step backward this season. 2015? Rookie of the Year. 2016? NL MVP. 2017? A whole lot of nothing. I guess, technically, those awards haven’t been announced yet, but I’m seeing a big ole’ goose egg coming his way in the hardware department.

The Cubs need to brace for what appears to be a sharp Kris Bryant decline. They can do this by trading for Boston Red Sox star third baseman Mike Olt. Like Bryant, Olt is a former first-round draft pick. But unlike Bryant, Olt is not exiting his prime.

Kris Bryant went from hitting 39 home runs in 2016 to just 29 home runs this season. This gargantuan drop-off in dingers is a clear sign Bryant is losing his power. He also drove in 29 fewer runs than he did last season. His slugging percentage dropped from .554 to .537. Disheartening to say the least.

The Red Sox probably wouldn’t want Bryant in return. They aren’t too keen on handling reclamation projects. But this way Olt could help mentor Bryant and perhaps turn him into a viable major league player again.

Olt is only 29 years old, so he could command the hot corner for years to come. The addition of his bat ahead of Anthony Rizzo would be absolutely lethal. “Bryzzo” is over. Welcome to the new age of “Rizzolt.”

ATLANTA, GA – SEPTEMBER 20: Edwin Jackson /

1. Edwin Jackson

I saved the best for last. The Cubs are currently without a “true ace.” Well, here he is. Edwin Jackson is without a doubt the greatest pitcher to ever be drafted by the Dodgers in the sixth round of the draft out of Shaw High School in Columbus, Georgia. That speaks for itself.

Edwin Jackson has basically played for every team in the league. The reason for this is because there is a constant and overwhelming demand for his talent. It’s time for the Cubs to be next on that list.

The obvious advantage here is that Jackson knows every team in the league, inside and out. He could relay all their strategies to the Cubs ahead of games. It would be just like when the St. Louis Cardinals hacked and stole information from the Houston Astros, only this wouldn’t be illegal.

The Cubs need Jackson’s pitching expertise if they wish to be legitimate contenders next season. Jackson’s 15-year career is filled to the brim with remarkable feats. An All-Star in 2009, a World Series champion in 2011, and one of the few pitchers in baseball history to throw a no-hitter, Jackson has done it all and then some.

Of all the players on this list, Jackson will be the most expensive. But the Cubs have assets. If Victor Caratini is ready to step into the starting catching role, Willson Contreras could make a good centerpiece in a package for Jackson.

Next: Cubs need Heyward to figure things out at the plate

There you have it, front office. Better get cracking. There is no wiggle room here. If there’s still space to make it happen, it might not be a bad idea to go after an outfielder as well. Jorge Soler is the first name that comes to mind. Here’s to seeing these new faces in 2018!

Home / Chicago Cubs News

Chicago Cubs: Five players the team ‘should’ pursue this offseason