Playing Pepper 2023: Chicago Cubs

If there is one thing baseball is good at, it’s tradition.  (OK, so that point could be debated with the changes over the last few years.)  Tradition around here states that the beginning of the season means that it’s time for Playing Pepper!  This is the fifteenth season–a decade and a half!–of the series that helps you get ready for the season by going around the league and talking with people that live and die with their teams.  Bloggers, former bloggers, podcasters, we’ve got them all as we take a tour of MLB and play some pepper!  If you get inspired to make some predictions during this series, this contest is open to fans of all teams so enter today!

Chicago Cubs
74-88, third in the NL Central
Website | Twitter | Twitter List
Last year’s Pepper
Top pitcher by fWAR: Justin Steele (2.6)
Top hitter by fWAR: Nico Hoerner (4.0)

There aren’t a lot of familiar faces, at least to Cardinal fans, in the Friendly Confines.  (In fact, one of the faces we would recognize now wears the red.)  Is this the foundation of the next great Cub team or just another cycle of disappointment on the North Side?  We’ve got some folks that actually watch Cubs games for fun to tell us all about it.

Contributor Site Twitter
Josh Timmers Bleed Cubbie Blue JoshFTimmers
David Miniel Cubbies Crib DavidAMiniel
Evan Altman Cubs Insider DEvanAltman
Neil Finnell Chicago Cubs Online TheCCO

C70: After another disappointing season, the Cubs seem to be making moves toward contention. What are your thoughts about this offseason and where the team stands going into 2023?

Josh: After two really lean winters, the Cubs had a really good offseason this year. Maybe it wasn’t a home run, but it was at least an RBI double. The front office’s plan to return to contention became clear—strong up-the-middle defense and a deep pitching staff that benefits from that. I’m a lot higher on Dansby Swanson than others for that reason—of all the free agent shortstops, he’s the one most likely to stick there as he ages. Jameson Taillon is a pitcher likely to benefit from having Swanson, Nico Hoerner and Cody Bellinger behind him. So will Marcus Stroman, who’s back for another season.

There are certainly still some issues that were left unaddressed and are likely to be problems. The Cubs have three first base candidates—Trey Mancini, Eric Hosmer and rookie Matt Mervis—that all have question marks. The Cubs are just hoping one emerges as a productive hitter. Third base is a similar issue with Patrick Wisdom likely to keep the job by default. And a lot of fans are upset about Willson Contreras leaving, although it was clear he didn’t fit in with the front office’s plan of “strong up-the-middle defense.” But overall, the Cubs are a better team than they were in October, and that means a successful winter.

David: Prior to recent events, off-seasons have been difficult to watch as a fan of this organization. Multiple pieces of the 2016 World Series team moved on to sign big deals, while Jed Hoyer and the Ricketts family sat on their hands, showing minimal interest in spending money until they landed Suzuki. The signing of Danbsy Swanson gave me a Jon Lester feel. It gave me hope that maybe this front-office is indeed working toward building another postseason powerhouse to succeed the Epstein-era. Similar to 2015, I’m expecting to see a mix of homegrown talent within David Ross‘s lineup card. 

Evan: The offseason certainly looks better for the Cubs in hindsight than it did in real-time, at least when judging it early in the winter. They ended up spending quite a bit of money to fill gaps in the roster and, while they didn’t land an ace or superstar position player, the emphasis on character and leadership appears to set them up nicely for the future. It’s possible to oversell the idea of chemistry, but it’s still important to have that little edge as you’re looking to build a team that can be competitive over time. I think the offseason was very successful for the Cubs in that regard and I believe they’ll be in contention for a postseason spot as a result of their improvements.

Neil: The Cubs had a good offseason. It was nice to see Jed Hoyer and Carter Hawkins put together a Major League roster. Since the trades, the Cubs fielded a minor league roster, for the most part, and it was way too hard to watch. It will be interesting to see how David Ross manages these players compared to what he’s had basically over the last two years.

The Cubs up-the-middle defense should be excellent. I thought the Cubs signed the best of the free agent shortstops in Dansby Swanson. He is such a good player with an excellent baseball acumen and that allowed Nico Hoerner to move to second. As long as those two are healthy, especially with no shift, there should be very few balls that find holes.
Cody Bellinger in center, Yan Gomes and Tucker Barnhart behind the plate. Good stuff. As long as they stay healthy, the Cubs pitching staff should be a lot better just by not having to throw to the team’s previous catcher. I like the addition of Eric Hosmer, even though he is only a place holder for Matt Mervis. The Mervis comp to Anthony Rizzo has me even more intrigued than I was before after the offensive explosion he had last season.

I am really pulling for Edwin Rios to grab hold of the third base job. Huge bat that could put up big numbers with regular at bats. And Trey Mancini, another solid big league bat that will help extend the lineup and the defensive flexibility to play every day. Then on the pitching side. I like the additions of Jameson Taillon, Brad Boxberger and Michael Fulmer. More big league players for a Major League baseball team. So, maybe I should have started this by saying the Cubs had a very, very good offseason and it appears the entire organization is trending up.

C70: Last year, contrary to popular expectation, Chicago held on to Willson Contreras and Ian Happ. I won’t ask you your thoughts on how the Contreras thing panned out, but what about Happ? Are you glad he’s back for another year and will he make it past the trade deadline again?

Josh: You can ask about Contreras. The front office just didn’t feel he fit into their plans to build a contender. It’s sad because he’s such a popular player, but I’m kind of numb to it after seeing so many of the heroes of 2016 leave over the past few years.

Happ is a really tough question. I’m glad he’s still on the team, but I also don’t know what his contract demands are. I know he wants to remain a Cub, but I also know he’s a leader in the union and those players often see it as an obligation to get the highest dollar to set a bar for other players. If he’s looking for Brandon Nimmo money, then the Cubs should deal him at the deadline. The other issue with signing Happ to an extension is that the Cubs have 3 consensus Top 100 prospects and they’re all outfielders. Cody Bellinger will be gone after this year so that opens up one spot, but Seiya Suzuki has right field reserved for the immediate future. You can’t count on all 3 outfielders to bloom, but what do you do if two of them do? Happ’s a team leader and a good player. If he’s willing to sign for 4 or 5 years and around $90 to $110 million, the Cubs will probably keep him. Otherwise, they’ll deal him at the deadline.

David: Despite Willson’s recent comments about the organization, I wish him nothing but the best. It was disapponting how the Cubs handled him, but it’s the dirty side of the business. What can you do other than move on? Of course, it’s great to see Happ back. Considering how things played out with Contreras, you can’t help but think the Cubs won’t allow history to repeat itself if they’re capable of selling around the trade deadline. Do I want him to remain a Cub? Obviously. Is there a possibility he is moved for prospects this Summer? Yes, it is very likely to happen.

Evan: It’s definitely surprising that Happ is still around given the Cubs’ willingness to trade him last season, but having him back this season is a good thing for the Cubs on a number of levels. He’s fashioned himself into a very capable left fielder to go along with offensive production that has always been above average, even if it’s a little inconsistent. The big issue here is that there doesn’t seem to be any urgency from either side to work out a long-term deal. Jed Hoyer doesn’t have a great track record when it comes to working out extensions and has already said that he prefers to work on deals prior to spring training, though the door could still be open to getting something done before they break camp. Happ is positioned to be one of the top position players in a free agent market that has just one big star, so he doesn’t need to jump at a team-friendly deal unless he really wants to. In the end, his time with the Cubs may come down to how competitive they are ahead of the deadline. If they’re in line for a postseason bid, they could hold onto him and then let him walk for a comp pick like they did with Contreras. But with a lot of outfield prospects coming up and the two sides seemingly valuing Happ’s future differently, it’s hard to see him in Chicago past this season.

Neil: Ian Happ has been very consistent at the plate since the break in 2021 and finally put it together for a full season last year. I was not a fan of Happ playing center, but left field is another story. I’m a big defense guy. That’s what is so often overlooked from the magical season of 2016, defense. With Happ in left and Bellinger in center, the Cubs will have a very good outfield. And if Seiya Suzuki could stay off the IL, there will be very few balls hit to the outfield that will not be turned into outs.

I think it was a good move Hoyer and Hawkins kept Happ and did not trade him. I was expecting an extension this offseason. I’m surprised it was not done. Hoyer was part of the front office that drafted Happ. So, he is one of their guys. I think Happ will be in blue pinstripes if the team is hovering around .500 at the break. And they will try to re-sign him next winter. If the Cubs struggle, Hoyer and Hawkins should trade him before the deadline. Don’t let him get away, like Kyle Schwarber, without any compensation.

C70: What are your thoughts about the pitching staff and how effective it can be?

Josh: There are two separate questions on the pitching staff. The starting rotation is solid if unspectacular. They’re the type of guys who will benefit from the improved defense. Jameson Taillon, Marcus Stroman, Justin Steele and Drew Smyly (Kyle Hendricks if he’s healthy)—none of them will win a game all by themselves but they’ll give the team a chance to win almost every time. I’m happy with the rotation.

The bullpen? Hoo boy. The Cubs have a lot of live arms there and they’re just trusting that some of them will emerge. They’re putting a lot of faith in their pitch lab to get the best out of these guys. Could it work? Sure. But it could also be a disaster. Who’s the closer? Who’s the guy who is going to get a key out in the seventh? No one knows at this point and they’d better figure that out.

David: I think this pitching staff will surprise us this year. The addition of Jameson Taillon was desperately needed with Hendricks sustaining the worst injury of his big league career thus far. I’m expecting Marcus Stroman to lead the charge with a solid campaign.

Evan: I’m growing more bullish on the pitching with each game because it looks more and more like a very solid rotation will be complemented by a surprising bullpen that has a lot of live arms. The Cubs are finally reaching the point where their efforts on the development side are producing pitchers who can come up and help the big club. They still lack a true ace at this point, though Justin Steele may have that kind of potential and Hayden Wesneski looks like he could be very legit. Their two big additions to the staff over the past two seasons, Marcus Stroman and Jameson Taillon, are very consistent. Drew Smyly is effectively their No. 5 at this point, so the floor is really high for the rotation even if the ceiling isn’t. The bullpen isn’t full of big names, but I think some of their young relievers will surprise folks this season.

Neil: The Cubs pitching staff should be quite a bit better than last season for several reasons. The addition of Jameson Taillon will lengthen the starting rotation and Hayden Wesneski has a chance to be a real difference maker. But the Cubs’ defense, especially up the middle and behind the plate, should make the biggest difference with the staff. I like four of the five projected starters (Marcus Stroman, Taillon, Justin Steele and Wesneski). I am curious to see if Kyle Hendricks will be a factor this season. And the bullpen should be good. The depth is there, and so is the length with Keegan Thompson and Adbert Alzolay. The additions of Brad Boxberger and Michael Fulmer in the backend should help the Cubs nail down close games. As is the case with every team, the Cubs have quality and on paper it looks good. How effective they will be all depends on health, obviously, and how the season starts. Confidence, confidence, confidence.

C70: What rookie (or player with very little MLB experience) do you think will have the biggest impact for the Cubs in 2023?

Josh: Cubs fans are all excited about Matt Mervis, who came out of nowhere last year to hit 36 home runs in the minor leagues. He was an undrafted free agent in 2020 out of Duke and was pretty terrible in low-A in 2021. Last year he made some changes to his swing and slugged his way from High-A to Triple-A. He hit at every level. The front office is understandably reluctant to just hand him the first base job, but he’s likely to force his way into the lineup sometime this year. Hayden Wesneski, who came over from the Yankees in the Scott Effross trade, could also be a big player, either filling in for Hendricks in the rotation or getting key outs in the bullpen. He was very impressive in his short major-league stint last year. The rest of the big minor league prospects are more likely to be 2024 arrivals.

David: I know some people are screaming for PCA (Pete Crow-Armstrong) or Matt Mervis but I’m going to mention Hayden Wesneski. Hayden stepped in nicely for the Cubs last year, yielding eight earned runs in six appearances. He showed some solid potential, striking out 33 batters while issuing only seven free passes. The 25-year-old righty should begin the year with the Major League rotation. 

Evan: At the risk of cherry-picking, I’m going with Wesneski on this one. If he stays healthy and is able to make 30+ starts for them, I don’t think it’s out of the question to believe he could be their best pitcher. That also means Rookie of the Year is a possibility. Matt Mervis is another one who could make a lot of noise, literally, if he’s able to get enough plate appearances this season. Right now, it looks like the Cubs might be looking to treat Mervis like they did Anthony Rizzo in 2012, which is to say he’ll spend the early months of the season at Triple-A to build up steam before being called up.

Neil: Hayden Wesneski. It looks like he will begin the season as the fifth starter in the Cubs rotation. Wesneski may have the best stuff in the rotation and I hesitate to say it, but like number 1 stuff on a winning team. Wesneski was so impressive last season and it’s been more of the same this spring. As long as he stays healthy, Wesneski should be at the top of the rotation in the second half. And if everything goes right for the Cubs this season, Wesneski could very well be the reason David Ross’ team is playing beyond game 162.

C70: What’s the best case, worst case, and most likely scenario on how 2023 plays out?

Josh: The Cubs need a lot of things to go right for them to make the playoffs this year, but the best case scenario is that they all do, they win 88 to 90 games and either win the division or snag a wild card spot.

The worst case scenario is that the offense doesn’t produce, the bullpen implodes and Happ gets dealt at the deadline. Then the Cubs end up winning 70 to 72 games and the fanbase will be looking for blood.

The most-likely case is that the Cubs take another baby step forward that leaves them still a bit short of a playoff spot, winning 80 to 82 games.

David: Best case? The Cubs prove they’re on the right track following the infamous purge. While some members of the current roster believe they’ve got pieces they need to compete, a lot can happen between now and the trade deadline. The worst case may not be all that bad. Move Happ if it means adding more to the farm system, and focus on the future. Most likely scenario? These guys go out and have fun like they always do. The stands will be full of energetic and passionate baseball fans enjoying a ballgame. Welcome back to the greatest sport, team, and fanbase on the planet. 

Evan: I think we’re looking at a team that could see a 20-game swing between best and worst cases. If the rotation is healthy and Cody Bellinger bounces back, among other things, we could be looking at 95 wins. The other side of that coin is a 75-win team that can’t make the most out of its upgrades. The more likely outcome is something at or just above .500, with 85 wins as the midpoint between the other scenarios. The key will be to avoid the long losing streaks they’ve suffered at various points over the last two seasons, which is something I believe the whole chemistry thing will help with.

Neil: When I first started this, I thought the Cubs would still be looking up at the Cardinals and Brewers in the division. I still think the Cardinals are too loaded not to run away with the division but, optimistically speaking, David Ross’ crew could push the Brewers for the second spot in the Central. Best case for the Cubs this season is 81-85 wins, realistically they are likely a 77-81 win team and competing, in the last week of the season, for the final spot in the playoffs. If everything goes south and injuries force Ross to field another Triple-A lineup, the Cubs are a 68-72 win team. There is a lot of positivity around this team for the first time in several years. It should be good season for the Cubs. And, if nothing else, I will be able to listen to the Hall of Famer, Pat Hughes on basically a daily basis … Chicago Cubs Baseball is on the Air!

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