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Chicago Cubs Rumors: A case for each trade deadline scenario

Jason Parini
Jason Parini

Da Windy City

(Photo by Nuccio DiNuzzo/Getty Images)

Before the clock strikes 6 PM ET on August 1 bringing about the 2023 MLB Trade Deadline, the Chicago Cubs front office has some decisions to make.

Only two weeks remain before the trade deadline at the time of publication and the Chicago Cubs currently sit at 45-51. They’re 8.0 games out of the NL Central lead and 6.5 out of the final National League Wild Card spot.

The Cubs started off the second half on the wrong foot, losing two out of three of a three-game homestand to the Boston Red Sox but rebounded well against the lowly Washington Nationals, taking two out of three including a 17-3 win in Game 2 of the series.

They now face off against the hated St. Louis Cardinals in a pivotal four-game set. At the time of publication, the Cubs had dropped the first game of the series and looked to bounce back in Game 2 with Justin Steele on the mound. The Cubs did win that game to tie the series.

The Chicago Cubs front office has some decisions to make before the deadline.

While it’s certainly not an insurmountable hill, the Cubs are quickly running out of time to convince management that they should be given the chance to go for a Wild Card or even a division title.

With a weak NL Central and 13 games remaining against the Cincinnati Reds and Milwaukee Brewers, the Cubs aren’t quite out of the division race though they’re close.

The front office has three options for the trade deadline. They can either sell off assets, buy pieces to contend for a playoff spot, or do nothing.

Let’s break down the three options and make a case for each:

Chicago Cubs, Marcus Stroman
Matt Kartozian-USA TODAY Sports

The Chicago Cubs could try to sell off some of their assets for the future.

Unfortunately for Cubs fans, selling off assets is looking more and more like the likely path. For the third straight year, Cubs fans will be on “hug watch” for the next week and a half.

But why exactly trade off assets for yet another year? Let’s break it down.

Pros: Let’s be honest. This team is not actually good yet. While they have some solid pieces, they’re still not a legitimate playoff contender and are still at least a year out from actually contending.

Top prospect Pete Crow-Armstrong is currently in Double-A and will not see the big leagues until next season. Their bullpen has been atrocious, their infield depth is non-existing and former All-Stars Ian Happ and Dansby Swanson are both hitting below .260.

By selling this year, the Cubs can add some more pieces for the future by trading off All-Star quality pieces that very likely won’t be returning next season.

SP Marcus Stroman is the top trade piece. The 2023 All-Star has had an excellent season, posting a 10-7 record with a 3.09 ERA.

While he’s owed $21 million next season, he has a player opt-out and will likely use it to pursue free agency and possibly get a multi-year contract with a higher salary given the market for starting pitching.

Also available could be OF Cody Bellinger, who has had a stellar rebound season. He’s hit .310/.365/.522 and since June 24, he’s hit .434 with 10 XBH. He has a mutual option for 2024.

But with a strong season, Bellinger very well could opt for free agency and pursue a multi-year deal as well.

In short, selling now would bolster their farm system and give them more assets for the future without mortgaging future contention or significantly shaking up the current roster.

The last thing the team and fans would want is to go for it now, give up too many assets, and then be stuck in purgatory in future seasons.

Cons: Another year of “hug watch”, selling off players, and likely a brutal August and September without the team’s No. 2 starter and their hottest hitter. It’s also not guaranteed that Stroman and Bellinger would hit free agency (although it’s probable).

While the team could opt to re-sign the two if they do hit free agency, the odds become stacked against them as players typically don’t come running back to the team that traded them.

It’s also disappointing that the Cubs aren’t a better team this year in a season where the NL Central is such a weak division. Heading into the All-Star Break, the first-place Reds were just nine games above .500.

It’s still not impossible for the team to add some solid pieces at the deadline and make a run at the division or wild card but selling at the deadline would obviously put a hold on any chances of that happening.

Chicago Cubs, MLB Trade Deadline
David Banks-USA TODAY Sports

The Chicago Cubs could buy pieces and add to their roster for a run.

As we said earlier, the Cubs aren’t exactly a good team. But they’re also not a bad team.

They’re 21-14 against sub-.500 teams and have won or split three of their last four series including taking two of three against the New York Yankees in the Bronx.

Could that be enough to convince ownership and management that the team deserves a shot to contend? Likely not. But let’s break it down.

Pros: As mentioned, the Cubs are generally winning the series that they should be winning and are only 8.5 games out of the division. They’ll soon be getting back former Gold Glover Dansby Swanson.

By adding some pitching pieces, a solid first baseman, and another bat or two, the Cubs could make a playoff run and gain important playoff experience for some of their young stars.

They still have 13 games against the two teams that they trail in the division as well as series against the White Sox, Cardinals, Mets, Royals, Tigers, Pirates, and Rockies, all of which are sub-.500 teams.

The Cubs do have numerous outfield prospects who they could trade and they could even give up a bit more prospects to get players with another year of team control.

Cons: It’s a wide gap between the Cubs and the top of the division as well as the wild card. If they did buy at the deadline, they’d have to mortgage their future to likely lose in the first round of the playoffs (or still not make it at all).

They also don’t have any series against the Padres or Marlins who they’re chasing in the wild card, so they’d need a bit of help if the wild card is their best path to the playoffs.

They also have a significant amount of pieces that they would need to acquire, so it wouldn’t be as simple as just adding a bat and a pitcher and becoming a winning team.

As tough as it is to watch an inconsistent, sub.500 team and have to deal with another year of selling off assets, it’s hard to rationalize being buyers with so many needs and inconsistencies on this year’s Chicago Cubs team.

Chicago Cubs, Patrick Wisdom
Photo by Nuccio DiNuzzo/Getty Images

The Chicago Cubs may do nothing and keep the roster as it is right now.

The third and final option is for the Cubs to remain neutral at the trade deadline.

Though it’s hard to imagine this happening, it’s more likely to happen than the team buying and trying to contend.

As a front office, you’re number one goal is to make the team better whenever you get the opportunity. Unfortunately, that won’t happen if they don’t do anything at the deadline.

Let’s analyze.

Pros: There are really only two pros here.

First, keeping the roster intact could be beneficial to the clubhouse. It’s tough seeing guys get traded and can mess with the team chemistry.

Second, keeping guys like Bellinger and Stroman could increase their odds that they return next year either by picking up their option or by signing an extension during the offseason.

Cons: There’s a lot of cons to this. The team remains in purgatory. You lose out on an opportunity to bolster the farm system for future seasons.

You possibly lose Bellinger and Stroman next year with no return for them. And barring a significant turnaround, the Cubs likely continue to play inconsistently.

The Cubs are also then left hoping that they get some help from other teams as well as likely falling further behind teams like the Marlins, Padres, and division leaders, all of which will likely buy at the deadline and become better teams in the hopes of making a deep playoff run.

Chicago Cubs, MLB Trade Deadline
Lucas Peltier-USA TODAY Sports

Get ready for “hug watch” as we wait to see what the Chicago Cubs do.

Ultimately, it makes the most sense for the Cubs to sell at the deadline and acquire some more young pieces for future seasons and an eventual contending season. The odds are significantly stacked against the Cubs in every sense.

They’re 8.0 games out of the division. They’re 6.5 out of a wild card without any games against two of the teams they’re chasing. It’s likely that Bellinger and Stroman opt for free agency this offseason, so it makes sense to get something for them and try to re-sign them.

There are just too many needs on the current roster to rationalize buying, and it wouldn’t be prudent to do anything and risk losing All-Star talent without any return.

It’s important for Cubs fans to remember that they’re still in the process of rebuilding. This year was never going to be a serious contention year and in reality, they’re still on track to put together a contending team once the young prospects continue to arrive and the team spends money.

But that shouldn’t happen until the timing is right. Unfortunately, that time is not now. After former team president Theo Epstein joined the Cubs in the 2011-12 offseason, the club didn’t make the playoffs until four seasons later in 2015.

The rebuild only began in 2021 with the sale of most of the 2016 World Series championship core, so let’s not forget that this is only year two of the rebuild.

There are better things to come, Cubs fans.

Jason Parini

Jason Parini

Jason S. Parini is a Contributor for Da Windy City FanSided. He was previously a Featured Columnist for Bleacher Report and has covered Chicago sports, Illinois Fighting Illini and Southern Illinois Salukis. Follow along for all the latest news and insight on the Cubs, Bears, Bulls, Blackhawks and more.