The Chicago Cubs were not supposed to be here. A subpar start to the season foretold their fate as trade deadline sellers. Before Aug. 1 even arrived, they were improbable buyers, acquiring third baseman Jeimer Candelario. Now, the team is 65-60 and is narrowly occupying a National League Wild Card spot. Baseball, huh?

This impressive turnaround validates an active offseason that was difficult for some fans to comprehend. Longtime Cubs catcher Willson Contreras was not dealt last year and ultimately walked out the door for nothing. Meanwhile, the organization shelled out a seven-year, $177 million contract for shortstop Dansby Swanson. A franchise that seemed on the verge of rebuild mode was suddenly acting like a contender.

That boldness rolled over into the regular season when general manager Carter Hawkins held onto impending free agent Cody Bellinger and possible free agent Marcus Stroman. These gambles all paid off, so much that we cannot merely attribute the success to blind luck. The Cubbies have restored stability to Wrigley Field through deliberate and savvy decision-making.

The only thing left to do now is hold on for dear life. With two paths to the postseason (division and wild card), Chicago can solidify itself as one of the feel-good stories of 2023.

But it won't be as straightforward as they or fans would like. A crowded race and a devastating injury could leave the club falling agonizingly short of a shot at October glory. Let's put these persistent Cubs under the microscope, as we break down the two biggest concerns facing them going into the playoff stretch run.

2. Cincinnati Reds

Before indulging the pessimists, it is important to identify the elements working in this team's favor. Chicago has one of the more underrated and balanced lineups in the league. A +64 run differential also portends good fortune, with no other trailing NL Wild Card contender outside the San Francisco Giants having a plus-total. Throw in Cy Young candidate James Steele and arguably the best glove in baseball in Swanson, and you have all the makings of a successful finish.

But this is one of the most bizarre MLB campaigns in recent memory. Aside from the dominant Atlanta Braves and the cruising Los Angeles Dodgers, the rest of the NL has been difficult to gauge. This free-for-all could take us all the way to the last day of the regular season. One of those potential thorns in the Cubs' side is their NL Central foe, the Cincinnati Reds.

This young and gritty bunch has breathed new life into Great American Ball Park. And while they may be gasping for air following a recent slide, the Reds are still standing. Much like the Arizona Diamondbacks, they have withstood the baseball gods' biggest and most humbling punch and have not shrunk into obscurity. David Bell's squad is just a half-game behind Chicago.

Their schedule, despite being one of the most challenging, presents them with an opportunity to grab a hold of their own fate. Cincy has a Wednesday doubleheader with the Los Angeles Angels before beginning an 11-game stretch against the D-backs, Giants and Cubs. This will be a make-or-break next week-and-a-half.

If the Reds again survive, their fans can take solace knowing that they end the year with the Pittsburgh Pirates, Cleveland Guardians and St. Louis Cardinals. Matt McLain has come through, Elly De La Cruz has pushed through the growing pains, Joey Votto is keeping spirits high and Andrew Abbott is dealing on the mound. This team has poise and composure beyond its years.

The pitching rotation is iffy, but it's getting healthier. Conversely, Chicago's has gotten weaker (we'll get to that in a minute). David Ross and company will also face a far more grueling final slate of games. Consecutive road series versus the Atlanta Braves and Milwaukee Brewers dampens the schedule advantage a bit.

1. Marcus Stroman's injury is a big concern for Cubs

The veteran right-hander was headed to this unfortunate list of red flags before he was placed on the injury list. Marcus Stroman was just not the same pitcher in July, posting an eye-opening 9.11 ERA in six starts. Something was off. He went to the IL with hip inflammation and recently suffered a major setback.

Stroman has been diagnosed with a right rib cartilage fracture. There is no current timetable for his return. A key strength thusly becomes a glaring question mark. The burden on James Steele and Kyle Hendricks might just be too cumbersome for the Cubs to overcome.

Making matters more complicated is that Stroman could enter free agency this offseason if he declines his player option. He has expressed a desire to sign a long-term contract with the organization, but management apparently deems it unwise to make such a big commitment to a good but not great starting pitcher. One thing is certain, though, the Cubs could use him for this postseason race.

Fans should be ecstatic by much of what they have seen in 2023. Cody Bellinger has reascended into stardom. Young players like Christopher Morel are holding their own and are laying out a nice foundation for the future. But optimism would be an unsatisfying consolation prize at this point.

The Cubs can have their cake and eat it too by clinching a playoff berth. It will not come easy, but nothing ever really does for this franchise. Would you have it any other way?