The Cubs have plenty of questions coming into the offseason. Whether it is who will be coaching them next year, big names on the trading block, or how to fix their pitching staff and bullpen, they have a lot on their plate this offseason. This offseason there are plenty of big names hitting the open market such as Gerrit Cole or Anthony Rendon. From my couch, I am going to layout what I think would be the best offseason plan for the Cubbies while they are on their couch watching the MLB postseason.

Listen to Trade Offers for Kris Bryant

I’m not saying trade him, but there is a route Chicago could take to end up with Rendon and a better farm system. Photo Credits to littleleague.org

Outside of Nico Hoerner, the Cubs farm system is one of the worst in baseball. What better way to revitalize that farm system than to trade Kris Bryant. Look, its not ideal to trade a former MVP. KB still has two years of control, however with MVP Candidate, Anthony Rendon hitting the open market, it could be beneficial to give the farm system a boost by trading Bryant and going after Rendon in free agency. Rendon has made it clear he wants to test free agency after he waited on accepting his 7-year $210 million offer from Washington. If the Cubs are overwhelmed by a batch of prospects for KB, they could end up accepting the deal.

I get he’s home-grown, he was part of the first team in 108 years, but Rendon and improved prospects outweigh having KB on the roster. Like I said previously, I am not saying trade Kris Bryant. However, getting rid of him could get some youngblood in the farm system and could create an opening for I don’t know… Anthony Rendon? The MVP candidate hitting free agency.

Explore Trades for Kyle Schwarber

Call it what you want, he is a DH. There has to be an AL team that would love a power hitting lefty-bat in the middle of their order. I do not know what a player of Schwarber’s caliber would have in trade value, but in a clustered Cubs outfield, it might be time to move on from him. Since his knee injury kept him from catching, Schwarber has played outfield in a time share for the Cubs. Sure he has his lumps defensively and hitting against left handed pitchers, but only 26, he has room to improve. But I think it’s time to field some offers for him to create a space in a crowded outfield with guys like Happ and now Castellanos.

Re-Sign Nicholas Castellanos

This is a must for the Cubs, as he has shown himself to be an elite hitter for the North-Siders. Photo Credits to theathletic.com

In his 51 games with the Cubs, Castellanos hit .321 with 16 home runs and 36 RBI. Castellanos hit more home runs in his 51 games with the Cubs than he did in his 100 games with the Detroit Tigers. If that isn’t enough for you to think the Cubs should re-sign him, well maybe his 1.002 OPS will be. Castellanos proved to be an absolute force for the Cubs down the stretch and should be resigned this offseason by Chicago.

The Bullpen

This was the biggest issue for the Cubs down the stretch. Kimbrel did not pitch up to expectation, Carl Edwards Jr. was traded to San Diego, Brandon Morrow was not healthy, Kintzler and Derek Holland were bad for the Cubs in the home stretch of the season. So who should they be looking at to boost what was a brutal bullpen?

Jake Diekman

He does have a mutual option for 2020. However, if that option is declined, Diekman should be a priority for the Cubs. I have been a firm believer that stuff and velocity plays, and Diekman has shown both. A 96 MPH sinker from the left side paired with an 85 MPH slider that he relies on primarily, Diekman has a nice repertoire of pitches that make him very effective. His ERA is not the greatest, a career ERA of 3.90 and this season finishing with the A’s had an ERA of 4.43. Although the ERA isn’t great, a power lefty is something the Cubs did not have this year in their bullpen, and Diekman fits the bill. If he declines the option, the Cubs should take a look at the veteran lefty.

Will Smith

This one is a loftier goal, but Will Smith was one of baseball’s closers this past season. 34 out of 38 in his save opportunities with an ERA less than 3, Smith could really bolster the back end of the Cubbie bullpen. On top of his impressive stats he is another lefty and will help in neutralizing the big left handed bats in the NL Central. The Cubs did not have many left handed options coming out of the bullpen at the end of the year, so going after and getting either Diekman or Smith, or both, would help the pitching staff take a significant leap heading into 2020.

Sergio Romo

A bit of a journeyman since his departure from San Fran, Romo is a veteran reliever who knows how to get it done. His slider is his best pitch, and he relies on it, throwing it almost 60% of the time. With good reason too, as hitters only hit .183 off of it. Romo, a key piece on the Twins roster, had an ERA of 3.18 since joining the Twins, and a WHIP that is less than one. He is a veteran that is very good at keeping hitters off the basepaths. Romo may not be blowing hitters away, but hitters only hit a measly .198 off him in Minnesota. He may not be the sexy move, but adding Romo to any bullpen, specifically the Cub’s, would be a smart decision.

Like I said, these are just suggestions, many teams should be in on signing all three of these guys, but with the Cubs bullpen struggles keeping them out of the postseason, they should be actively trying to pursue at least two of the three listed.

The Head Coaching Situation

If you are reading this, you probably know the Cubs and Joe Maddon just parted ways. So that leaves the Cubs without a head coach heading into the offseason. But do not fear, there are many potential candidates that could put the Cubs over the top for 2020.

David Ross

Already a fan favorite from his time with Chicago, David Ross makes for a viable candidate to coach the baby bears. Photo Credits to abc7chicago.com

He already has a good relationship with most of the team. With the new wave of lineup decisions driven by analytics, Ross could play a very similar role as Boone is playing for the Yankees. Ross had already played a coach-type role for the Cubs during their 2016 World Series run, so he would just be stepping into a role similar. Because he has relationships with guys like Lester, Rizzo, Bryant (granted he stays), they might see him as a teammate rather than a coach. That is a risky game to play as a coach. As much of a fan favorite and good buzz it would bring to the Cubs, I do believe there are better options.

Joe Girardi

I personally think this is the best option for the Cubs. Girardi has ties to Chicago as he grew up in Peoria, went to Northwestern for school, and also played for the Cubs. Granted he has had clashes with front offices in the past, he brings a mentality that will be very different than the one Maddon brought to the Cubs. Girardi will be more strict, and more of a hard-ass than the young players on the Cubs have seen, but after missing out on the postseason this year and losing in the NL Wild Card game last year, maybe a shift in culture is necessary. The knock on Girardi is him not believing the effect of advanced analytics in today’s MLB. But, he is starting to adopt to the new wave, and with the right staff around him, Girardi could be a spectacular fit for the Cubs.

Joe Espada

Espada is the Astros’ bench coach and has been since 2017. He has been a scout for the Yankees, and worked through the Marlins coaching system since his 10 – year minor league career ended. The MLB is a copy cat league, when one team has success, many teams take a look at what they are doing and try to steal ideas. Well instead of stealing ideas, why not take one of the coaches for what has been a dominant Astros team. Like I said previously, the Cubs pitching staff has not been great, so hiring a coach that has worked for the team that has revitalized the careers of Justin Verlander and Gerrit Cole could be a boost for the Cubs staff.

The Cubs more than likely will not be the only team interested, as his background around baseball could make him a viable candidate for a head coaching position. That being said, the Cubs should make him a priority alongside of the David Ross, Will Venable, and Mark Loretta who are all going to be interviewed.

Find a way out of Addison Russell

Even though Theo Epstein said he is available, Javier Baez should be the Cubs’ shortstop for the upcoming years, which means what for Addison Russell? Photo Credits to nbcsports.com

With guys like David Bote, Ben Zobrist, Ian Happ, and now Nico Hoerner, is Russell needed for the Cubs? Defensively, Russell is one of the best up the middle, but offensive struggles and off the field issues have kept him on the bench and eventually found him getting optioned to Triple-A. If he isn’t playing as well as he showed in 2016 and he isn’t getting consistent innings, why should the Cubs keep him? They have to find a trade that will get them out of Addison Russell. The fans don’t want him, and he certainly hasn’t played well enough to find playing time in a deep Cubs infield. So once again, why keep him?

Call the Red Sox, see what it may take for one of Mookie Betts or J.D. Martinez

Alright, this one may be a little lofty, and every team should do it. But, I have mentioned the Cubs depth a lot, why not get rid of some of that and get a superstar. The Red Sox have stated that they will not be able to pay both, so maybe Theo can go after one of the two stars from the team he formally was the GM of.

For Mookie, it will be a heavy package the Cubs will send that will probably have to send Boston. But it is Mookie Betts. If I was Theo, I’d give Boston a list of players that can’t be touched and go from there. Let’s say Chicago does make a trade out of KB and gets more prospects, those prospects would have to be included, maybe Hoerner? Happ? Almora? Bote? All of those guys will be on the table, but the one guy that Boston should absolutely go after is Schwarber. Boston would love that guy hitting 40 bombs down the short porch in right, and Schwarber could finally DH.

For J.D., the deal for Chicago will be a tad lighter. But Boston should be trying to get Schwarber regardless of who they are trading to Chicago. The same guys will be on the table, but it will take less of a haul from the Cubs due to Martinez’s deficiencies in the field and his age compared to Betts.

Get another Big Game Pitcher

Another offseason plan that many teams should be doing. However, for the Cubs it is different. Lester is only getting older, and his numbers are getting worse as time goes on. On top of that, Quintana and Hamels could be free agents this offseason. Alec Mills was a nice addition for the Cubs starting staff near the end of the year, but he is not a starter by trade. The Cubs need a high quality starter, now it doesn’t have to be Gerrit Cole, it would be great if it was, but that’s very lofty. There are plenty of quality pitchers on the market that the Cubs should be taking a peek at.

Jake Odorizzi

Coming off an All-Star level year in Minnesota, Odorizzi has been a steady starter all year for the Twins, and should continue into the postseason. An ERA of 3.51 and a record of 15-7 should make Odorizzi a hot commodity in what is a loaded free agent starting pitcher class. He can slide into the #3 role behind Hendricks and Darvish for the 2020 Cubs if they sign him, and a 4 man rotation of Hendricks, Darvish, Odorizzi, and Lester is not the best in the league, but it is in the upper tier of starting rotations if everyone remains healthy.

Zack Wheeler

An 11-8 record with a 3.96 ERA, Wheeler was a key factor in the Mets playoff push. Similar to Odorizzi, many teams will be taking a flyer on the right-hander. Adding in another hard thrower in Wheeler, alongside of Darvish is a nice counter to Lester and Hendricks. If he can stay healthy, he will be an above – average starter to have whether he is a #3 or #4, which is exactly what the Cubs need.

Rick Porcello

Similar to Wheeler, Porcello is another guy who’s been a #3 or #4 for most of his career. Whether it was pitching behind Chris Sale and David Price or Justin Verlander and Max Scherzer, Porcello knew his role and succeeded in it. Porcello’s main pitch is the sinker, and for a Cubs team that did not give up many home runs this past season, Porcello will fit right in with his ground ball – dominant pitching style.

There are plenty of other pitchers that fit the mold of an upper – tier #3 starter I am looking for the Cubs to sign. Whether it is one of the three listed, or pitchers such as: Tanner Roark, Wade Miley, or Michael Pineda, the Cubs have plenty of options to deepen their starting staff.

There are certain issues that do need to be addressed for the Cubs. Whether it is who the head coach will be, the bullpen, or trade rumors around some of their stars, all are questions around the Cubs heading into the offseason.

Featured Image. Five Questions facing Cubs this offseason | Chicago Cubs. Photo Credits to MLB.com