It happens every offseason.

The Chicago Bears draft a fresh class of rookies or signs an exciting free agent or two, and the NFL whips up a new batch of jerseys for fans to purchase. How many of you guys ran out to get a Muhsin Muhammad #87 in 2005, a Julius Peppers #90 in 2010, or a Kevin White #13 in 2015?

Muhammad’s Bears’ career was most memorable for his quote about Chicago being, “where receivers go to die.” Peppers made four straight Pro Bowls, but after being released he ended up playing north of the border. And White’s career never got on track.

But not every jersey purchased has a cautionary tale attached to it. Brian Urlacher’s #54 had staying power, as did Devin Hester’s #23.

In our latest WCG offseason, roundtable topic, we wanted to know the answer to the following question.

What’s the most embarrassing Chicago Bears jersey to own?

Considering I’ve never owned a Bears jersey, I’m not sure I’m qualified to answer this one. If I were to ever get a jersey (but I probably won’t because I’m very cheap), I have a strict throwback-only rule. I’d never buy a current player because with free agency there’s no telling how long he’d be relevant. In recent years there have been several Alshon Jeffery, Jordan Howard, and Brandon Marshall jerseys purchased by fans. I’ve seen Grossman, Terrell, and Enis in my travels. My advice to jersey buying fans, stick with the classics like #34, #50, #54, #23, #57, #33, #65, #99, #95 and #81.

Here’s how a few of our other staffers answered today’s topic.

Jeff Berckes - Buying the jersey of anyone the Bears drafted gets an automatic pass from me as there is always hope that player will develop and / or live up to expectations. I think the worst thing you could do is buy the jersey of a player who played the vast majority of his career for an enemy squad and signed on for one last run with the Bears. In recent history, that’s Jared Allen. Owning that jersey tells me you’re either related to Mr. Allen or a closet Vikings fan.

Sam Householder - I think this is a case of it has to be a player that was so bad that not only did he bust out as a player but also as a person. At least you can rock a Kevin White jersey and be like ‘hey he was a nice kid that got hurt, that’s too bad.’ But David Terrell it’s like ‘He was bad and kind of an a-hole.’ And then it has to be someone that the burn has kind of worn off but is not so old that you can wear the jersey ironically (like a McNown or Enis jersey). So I think like a Jeremiah Ratliff jersey or a Ray McDonald (did they even sell those though?) would be embarrassing. Of ones that are still out there though, Brandon Marshall has to be up there. Sure he set a lot of records but he has a lot of issues.

Erik Christopher Duerrwaechter - Any jersey previously worn by a Bears QB not named McMahon, Cutler, or Trubisky.

Ken Mitchell - There are several levels of cool, jerseys, and a few that are just embarrassing. Let’s start with several types of cool ones. First, there is any Bear in the Hall Of Fame. Secondly, any easily recognized Bears great like Jim McMahon, Kevin Butler, Keith Traylor, Israel Idonije, Thomas Jones, Matt Suhey Olin Kruetz, Mike Brown even up to guys like Josh Sitton. Bearman Don Wachter be inducted into the fans wing Hall Of Fame for fans this summer in Canton, Ohio wearing Doug Plank’s 46 jersey. Then there’s the “obscure cool”, show up at any function wearing 87 (Tom Waddle), 85 (Keith Jennings), 67 (Jerry Fontenot) or 37 (Tony Parrish). The most embarrassing ones are for the flops... I mean absolute flops... Show to the tailgate up wearing Kevin White’s 13, or David Terrell’s 83 and you deserve to be mocked.

I wanted to open this roundtable up to the fans too, so I posed the question to our Facebook and Twitter audience.

This is a picture. Would post my Grossman Jersey but I had to sacrifice that Jersey at a jersey burning party. True story. pic.twitter.com/3MVgarFH3A — Keith DeVore (@kjdevore28) May 22, 2019

Once saw a Conte Jersey floating around. — Zachary Lekfield (@ZLekf) May 22, 2019

Jon Bostic and Shea Mclellan jerseys are still in my closet if anybody wants one — Extremely Sioux City Guy (@reallycooljohn) May 22, 2019

I won a Jared Allen autographed Jersy st a cancer shoot,I was the only one that put a ticket in for it — Jasper Fenix (@jasperfenix9) May 22, 2019

I have an authentic kordell Stewart, Jared Allen, Tank Johnson, and Kevin White. — Dan Aguire (@bearsfan_dan) May 22, 2019

I bought a Bryan Cox 52 jersey. It said B Cox on the back. Tore the name off when they traded for Mack — Richard Bunts (@Elephanthole) May 22, 2019

Now it’s your turn. What’s the most embarrassing Bears jersey to own?

And if you own one you’re embarrassed of, share a pic in the comment section!