If there's one milestone marker that Cubs fans have become increasingly aware of in each of the last three years, it is the MLB Trade Deadline. Since Jed Hoyer has taken over the reigns as the President of Baseball Operations from Theo Epstein in 2021, it has become the doomsday clock for the roster. In the previous two seasons, the writing had been on the wall. Jed's first two seasons led to selling off once none of the core of the 2016 World Series championship roster was able to reach extensions being in the their final years of club control before reaching free agency and 2022 being wholly non-competitive from the outset. Most of us would argue those teams were DESIGNED to sell. I don't know how much argument you would get from even the most optimistic fan.

2023, in general, has been a step in the right direction in some aspects, but has also created a lot of questions. In the offseason, the narrative was that this team could compete for a division title if a few things broke right: the breakout years of Nico Hoerner and Ian Happ were replicated and/or surpassed, Seiya Suzuki took a step forward after having an excellent second half last year, some of the reclamation pieces the Cubs brought in through free agency were able to regain old form, and no one in the division ran away from everybody else. In that list, it has been a mixed bag and brought us to where we are. Nico has had stretches of being great followed by stretches of deeply struggling. Ian Happ and Seiya Suzuki are slugging under .400. Cody Bellinger has provided stability and power in a lineup that hasn't been able to consistently find it. Justin Steele, Dansby Swanson and Marcus Stroman have been All-Stars. All in all, it puts us exactly where we are: hovering around a few games under .500 and 5-8 games back in the NL Central.

That leads us to the ultimate question(s): what are the Cubs going to do at the Trade Deadline? Even more importantly, what SHOULD they do? In a vacuum, it is black and white. If the Cubs cannot contend for the NL Central title or one of the Wild Card spots, they should trade the expiring contracts who could possibly depart through free agency in the winter. That's how it has played out the last two years and if I'm being honest from where I sit right now, it is how it will play out in a couple weeks. However, the Cubs have been reluctant to declare one way or another whether they are buying or selling and for good reason. As we look at the 2023 Cubs and where they stand heading into 2024, this is an imperfect roster. There is a shortage of true, needle-moving impact players on both sides of the ball that will not be easily addressable. Free agency from a positional standpoint is dry in 2024. The Cubs need an infusion of power on both sides of the ball to remove some of the "randomness" of baseball. Luck plays a lot less of a factor when you can add three runs on a single swing and that's something they desperately need to add.

A crucial factor to consider is that Jed Hoyer does not have an unlimited amount of time to see his vision through. If another sell-off is imminent, it means another season of decreased attendance and TV ratings. The Ricketts family has invested in a streaming service and a sportsbook to add revenue. Disinterest in the team actively hurts those investments. If people do not care about the team, it is damaging the bottom line. Piecing apart players who could contribute beyond this year and not making it the highest of priority to retain them probably sets this team back another year. There aren't a lot of alternatives. Prospects are starting to reach the upper minors but cannot be depended on to transform this team instantly. Either through injuries or initial struggles, they have to be offered patience. Expecting them to come up and transform the franchise puts everyone at risk. However, letting them supplement existing pieces and adding on the margins can put this team in a position to compete for the division title and keep fans at the ballpark. I don't think that is something the Ricketts are going to be willing to wait on much longer.