DePaul’s Sisyphean Hoop Dreams: Why Hope Hurts More Than Losing

Picture this: It’s a Tuesday night in the South Loop. The wind off Lake Michigan is doing that thing where it feels less like weather and more like a personal insult. Inside Wintrust Arena, the lights are NBA-bright, the court is pristine, and Chris Holtmann is stalking the sideline with the intensity of a man trying to defuse a bomb with a pair of rusty pliers.

You look up at the scoreboard. DePaul is down by eight to Marquette. Again.

But this isn’t the apathy of the 3-29 disaster from two years ago. This is something worse. This is the agony of competence meeting a glass ceiling. For decades, the DePaul Blue Demon dilemma was simple: bad coaching, bad facilities, bad vibes. Now? They have the coach. They have the arena. And yet, here we are in January 2026, staring at the same middle-of-the-pack purgatory.

The Ghost of June

To understand the current mood in the student section (which, to their credit, is actually populated this year), you don’t look at the box score. You look back to June 30, 2025.

That was the day the notification popped up on thousands of phones across Chicago: Amsal Delalić, the 6'7" sharpshooter from Pitt who was supposed to be the skeleton key for Holtmann’s offense, was out for the season. Just like that.

It felt scripted. A cruel joke written by a screenwriter who hates happy endings. (You almost expected the ghost of Ray Meyer to sigh audibly from the rafters).

In sport, we love to talk about "next man up." But in the NIL era of college basketball, depth is a luxury item that schools like DePaul struggle to afford. When you lose your projected breakout star, you don’t just lose points; you lose the margin for error. DePaul has been playing this entire 2025-26 season with one hand tied behind its back, scraping for wins that felt destined in August but look impossible in January.

The "Chicago" Paradox

We need to talk about the city. Being "Chicago’s Team" is a great marketing slogan, but in practice, it’s a logistical nightmare. DePaul is fighting a war on two fronts.

On one side, they are a private Catholic university trying to compete in the Big East—a conference of sharks like UConn and Creighton who have turned basketball into a religion. On the other, they are trying to capture the attention of a pro sports city that only cares about winners.

"We built the plane while flying it, but it turns out the other guys are flying F-16s while we’re in a very reliable Cessna." — Anonymous Big East Staffer on the NIL gap.

The House v. NCAA settlement, which kicked in last July, allowed schools to share revenue directly with players. Sounds fair, right? But equity isn't equality. A state school with 50,000 students and a football TV deal has a different revenue engine than a private school in Lincoln Park. Holtmann is a fantastic mechanic, but he’s trying to win a Formula 1 race with a budget cap that his competitors don't seem to feel as acutely.

The Pain of Hope

Here is the twist that no one admits: Hope is exhausting.

When the team was winning three games a year, you could detach. You could laugh about it. Now? You watch CJ Gunn diving for loose balls, you see Holtmann drawing up brilliant out-of-bounds plays, and you believe. That belief makes every six-point loss to a ranked team sting like iodine on an open wound.

The Blue Demon Dilemma isn't just about wins and losses anymore. It’s about the realization that "fixing" the program was the easy part. The hard part is surpassing the structural reality of modern college athletics. DePaul is doing everything right. They have the right coach, the right grit, the right collective. But in 2026, doing everything right might only be enough to finish 10th in the Big East.

And that, my friends, is a much harder pill to swallow than incompetence.