Windy City Gridiron picks Bears-Browns

Football misery thy name is Cleveland and a lot of the time, Chicago.

While not exactly known for their consistent success, one can take solace knowing the Bears have it better than the Browns. Not a difficult task, mind you, but a fact, and moral victory nonetheless. For comparison’s sake, the last quarter-century or so — let’s say 28 seasons — is an excellent place to start. I would never share something arbitrary, something bereft of logic on a small sample size. Football melancholia is too important.

1994 is a fantastic starting line. What is Midwestern football, if not a sad exercise hoping for tiny bits of schadenfreude?

It’s difficult to be more mediocre than 178 total wins in almost three decades of play — roughly six wins, on average, per season — but the Browns have the Bears beat here. 129 wins in 28 years, or an average of about four wins per season or so, is the lowest of the low for Dawg Pound visitors. That kind of mark screams, “Only beat other bottom-feeding teams, with a roster that will be very different come next season, and ruin better top draft positioning, year after year after year.” It’s a rhythmic chant of “time to peruse mock drafts and tell myself this occasion is better, there’s always next year, I hope, in October.” It’s drinking or eating or spectating sports sadness away and goodness, perhaps, reading a book (?) instead (?).

Chicago has only seen seven total postseasons since 1994. Like many, many, many NFL teams, the Bears are known for extended absences of even relevant December football. Seriously, the business model relies on nihilism. Look it up. Suppose I got my deep scars from watching many a quarterback capable of imploding potentially any moment, without warning. There’s a significant chance that someone, somewhere else on the other side of the country, has a matchable arsenal of horror stories about how their venerable squad did not hold it together when, in fact, they really should have. Such is life. (Tom Brady, one individual player who ceases to be mortal and almost certainly has an investment in some sort of Lazarus revitalization project, has won seven Super Bowls since 2001.)

Now I know, a 25 percent appearance rate in real do-or-die games isn’t anything to write home about. Hell, I would hide that unrelenting shame from my family forever if I could.

Are you kidding?

That’s unseemly and utterly embarrassing. I’ll never mention it. Yeah, I’m seeing someone, Aunt Anna. We’ll talk about that first. They’re amazing. Anything else, please. But ahem, Cleveland has earned a mere three playoff berths in the same time frame. That’s only one more instance (3) than there have been Great Conjunctions (2) since, otherwise known as incredible lunar events where everything has to be in the perfect place at a perfect moment of serendipity. Space miracles, in other words. But, to be fair, I suppose a Browns postseason qualifies for a miracle under similar parameters.

The most faithful marker of a lack of football dignity is how often your organization brings up the rear amongst peers and rivals. The Bears are in better shape than someone else here, too. Shocking, I know. Where Chicago has finished in last place in the NFC Central-turned-NFC North 10 of the previous 28 years, Cleveland has concluded in last place in the AFC-Central-turned-AFC-North 15 of the previous 28 seasons. Yes, Dearest Reader. More than half of a young millennial’s lifespan has seen the Browns looking up at Pittsburgh, Baltimore, Tennessee, Houston, and, oh my God, even Cincinnati.

How cruel. Anything you can do better, I can do worse.

As the two organizations reunite this weekend in what does not seem like a Toilet Bowl matchup, for once, I would be remiss if I didn’t give the Browns due credit over the Bears. After a cathartic smashing of the Steelers last January, Cleveland ended a 27-year playoff win drought. 27 years without ever making it to the final eight of the dance. With the monkey (dog for the Browns, right?) off their back, a prototypical contending squad with headliners like Myles Garrett, Nick Chubb, and Odell Beckham Jr. now sits in a position to win a playoff game in consecutive years for the first time in well over three decades. For a franchise that I once thought might have been better off being relegated into a dark corner, that’s a massive step up. Bernie Kosar—they are coming, and they are rowdy.

The Bears, meanwhile, haven’t seen sudden death victory since Frank Omiyale and J’Marcus Webb was their offensive tackle pair. It’s easier for me to find grainy, hastily uploaded footage of a Bears playoff win on YouTube from someone sitting in Soldier Field’s nosebleeds than high quality, unfiltered highlights of the Bears humiliating an over-the-hill Matt Hasselbeck again.

There is hope with Justin Fields. Funny what a real quarterback prospect can do for the spirits. Still, for the first time I can remember, I’d consider the Bears to be looking up at the Browns, if only on a temporary basis. Thankfully, I have a hunch Fields at least makes this race neck and neck, and very soon.

But, for now, I suppose I can revel in Lions misery as a healthy projection. I feel good about those prospects. They haven’t failed me yet.

Windy City Gridiron picks Bears-Browns along with every other NFL game in Week 3.