People With Passion: RedEye's BAG BOY

People With Passion: RedEye's BAG BOY

In August of 2004, with RedEye still searching for its own identity, RedEye sports editor Chris Malcolm and a writer who shall remain nameless developed an idea for a column that would encapsulate the Chicago fan experience: caustic yet passionate, humorous yet desperate, hopeful yet exacerbated. The character was Bag Boy, and since 2004 this anonymous writer has penned over 500 columns documenting the Chicago sports landscape, along with a smattering of video reports and countless Five-on-Five contributions.

In that time, the Bag Boy column has secretly become one of the best ongoing sports columns in Chicago. I say "secretly" not because the writer’s true identity is a secret, but rather because that hidden identity and the inherent gimmick of writing under that kind of pseudonym obscures the true source of the column's potency, which is that it best reflects the way that sports fans interact with their teams. It's never about just one team – it's always about the role that each team's performance plays on the others.

In other words, the return of Derrick Rose mattered on its own terms but also because it helped soothe the hardship of watching the Bears, Cubs, and Sox. His new injury hurts for the same reason, while the Blackhawks winning the title mattered on its own terms, but also because it helped soothe the pain of Rose missing the 2013 playoffs. Or to go back to a prime example 12 years ago, the 2001 Bears were important in part because the rest of the Chicago sports landscape was so dismal at the time.

Here, in this email interview with the man inside the bag, we discuss the character’s origins, the Chicago sports fan mindset, and the past ten years of Chicago sports. A big thank you to RedEye web editor Brian Moore for facilitating this interview.


I have to start by being completely honest: the idea for the Bag Boy column did not come from me. It was created by the sports editor of RedEye in its early years. However, we view the world of sports in very similar terms. That is to say, we find large portions of that world to be absurdly funny. We find the fact that Chicagoans spend inordinate amounts of time, energy, money and emotion on this silly part of the world just bizarre.

So the character of Bag Boy was based on these extreme emotional reactions to these Chicago teams that consistently break his heart. His reactions tend to be negative, but I found that to be too limiting in terms of character and perspective. After all, the fun of being a sports fan in Chicago is also the freedom to overreact positively, especially if the teams win on opening day.

The decision was made to make him anonymous because he remains more of a symbol of what the typical fan is thinking, as opposed to an individual personality. Also, just as important, it gives me certain freedoms to say things that really need to be said. And I'm not saying them for my own personal attention – no one knows it's me.

One thing I have always tried to do with the column is to look hard at situations and determine the truth of them. Once I determine that, I add all of the bizarre emotional reactions (or over reactions), such as humor, warmth, references to movies, TV, and other pop culture, and then tie it all together.

The style of the writing comes from a few different influences. I have an improvisational comedy background, and write very much as I speak – in a free form matter, but always ready to connect different situations comedically. As I start to write, often times I'm not sure how I'll connect the dots, but I trust that I will.

And the other influence, believe it or not, is Hemingway. I have read much of his work and though I am no master, I have fallen in love with the short, declarative sentence. And since it's only 350 words a week, I am forced to be extremely efficient with the words I use. So the style not only fits the column but our times, as people only seem to want shorter length pieces.


Soooooo much here I want to review, but let's start with the setting, August 2004 (or even more generally, Summer 2004) because the Bag Boy column is so much about capturing one particular week in Chicago sports history, and the state of the teams is very important.

If I recall correctly, in the summer of 2004 Chicago sports had one thing going for it in a team-that-could-win-a-title sense, and that was the Cubs. I think they were already significantly behind St. Louis by August, but they were in the wild card hunt, and maybe the frontrunner. They had Lee/Alou/Aramis/Sammy all in the midst of 30 HR seasons... they had Maddux in the rotation with Kerry, Prior (battling injury), Z, and Clement... and they would have juuuuuust made the Nomar trade, which as far as everyone was concerned would prove to be the missing piece. And not just because he was better than Gonzalez, but because it exercised another piece of Game 6.

As for the other teams, we had three new coaches/managers: Ozzie was in the middle of his first season, Scott Skiles had just wrapped his first season (though he was hired midseason), and Lovie was preparing for his first season. I think the NHL was either locked out or about to be locked out, but honestly I didn't follow hockey at the time. The Sox were struggling, and there was no real glimpse that they would win the World Series the next year.

The 2004 Bulls was one of the biggest season disasters I had ever seen, and that's saying something. Do you remember the 2004 team slogan? It was, "History In the Making," because they won 30 games in '03. Then after this calamity of a season where they fired their coach and traded half their team, the 2005 team slogan was, "Through Thick and Thin." Now that's comedy.

And the 2004 Bears were preparing for Year 1 of Lovie and what amounted to Year 1 of Rex.

I bring all this up because for the column you write, things were about to get REALLY fun for you. From November of 2004 to February of 2007, we saw...

  • The Bears surprise everyone by winning eight-straight games with rookie Kyle Orton to win their division.

  • The Bulls continue their ascent, making the playoffs again in 2006 and then being in the running for best team in the East in 2007.

    • The Bears continue their ascent, winning 13 games and making the Super Bowl.

I was out of state until late 2006, and I wasn't reading RedEye until late 2007. Tell me about what that early stretch of the column was like for you. What were the early changes in the column? How quickly did you feel like you had the character down? What was the readership response like? And how did Bag Boy respond to such unfettered success from the Sox, and then to a lesser extent from the Bears & Bulls? That must have been an early test to the system.


You know how when you're angry about something or notice something in the news that doesn't seem right and you feel the need to reach out to your (hopefully close) friends?

Before texting and twitter and facebook, there was just plain old e-mail. Sometimes when I think of the column, or as I'm writing it, I think it should have that tone of an angry e-mail to good friends. "Hey guys, you see this play last night? What was Cutler thinking?"

Anyway, very observant regarding 2004. I say that because one of Bag Boy's strongest convictions was formed that year. I'll explain.

Bag Boy, for some strange reason, survived the 2003 Cubs intact. If anything, the 2003 Cubs were a very pleasant surprise. It was Dusty's first year with the Cubs. Repeat: first year. I think everyone would understand if they were an average team that year but they weren't – they went to the playoffs! Then they won the series against the Braves! So really, the whole time I'm watching this I'm still thinking, "This is great, but this feels ahead of schedule. If it all ended, I'd still be ok." Which is exactly what happened. Albeit tragically.

Still, I think of those Cubs as a pleasant surprise. I think they only won 88 games or so, so it's not like they were unstoppable. Their pitchers were good... but young.

2004 felt much, much, different. Those guys were expected to win the division and the World Series. Sports Illustrated put them on the cover – the kiss of death! And they changed their formula and it bothered me. In ‘03, they had two guys at the top – Kenny Lofton and Mark Grudzielanek – who were absolute masters at taking pitches, working pitch counts, drawing walks, and setting up Sosa and others for big RBIs.

For whatever reason, they go with Corey Patterson in that role in '04 and he sucks. He just sucks as a set-up guy. Sosa continues to strike out like crazy, and the '03 chemistry isn't there despite the additions you mentioned.

Anyway, it's the last week of the season and they don't win the division. I'm angry but there's still the wild card. Oh, and they also tried to make LaTroy Hawkins, a bonafide set-up man, a closer.

And he blows. I mean he mentally breaks down and can't handle it.  The whole team seems to mentally break down and can't handle it.

We have Kent Mercker calling the press box and complaining about Steve Stone's calling of the game. (Shouldn't he be watching the game?) We have Dusty complaining about that on WGN radio as well. And of course the Cubs blow the wild card the last week as well. Dusty, a renowned player’s coach, seems content to pick media fights and side with his players, and that offended me greatly. The result is the Cubs lose Steve Stone – who was generally regarded as the best TV analyst working at that time.

And… there just didn't seem to be any outrage. No calling out of anyone. And that's when it really hit me/Bag Boy: Bag Boy hates the Cubs. And I mean truly hates the Cubs. He can handle mediocrity, he can stomach ups and downs, but he cannot tolerate the way mediocrity is quietly accepted at Wrigley Field, and even embraced and treated as cute and cuddly. Bag Boy cannot do cute and cuddly.

Because starting in 2003-2004, really, the Cubs said, "We're here to win." The Cubs are big, big business. They charge big money for premium opponents and they've been trading on the Wrigley atmosphere for far too long. 2003-04 is also when the Red Sox started winning titles, so it was proven that it can be done in older stadiums. So though it's never explicitly stated, Bag Boy hates the Cubs and avoids mentioning them. There is only so much hypocrisy that Bag Boy can take and the Cubs crossed that line in 2004.

You're spot on regarding Ozzie and the White Sox. No one would have said at the end of ’04, "Man, these guys are going to dominate next year." That really made 2005 a great, fun experience to cover as Bag Boy. The 2005 White Sox were just one of those great Chicago teams that I really loved. Their pitching was sick, and they got just enough hitting from Konerko, Aaron Rowand, Jermaine Dye and others to make it exciting. They just pitched like crazy and executed. And Ozzie made it fun.

So 2005 was very very special. I remember the column I wrote when the Sox won it all. Bag Boy could not be negative – I wouldn't go that route. I went with honesty and simply sent a thank you note to all the players for their heart and dedication. Because I think Chicagoans, as much as they say things like, "Cubs suck, Sox rule," run deeper than that and really appreciate heart and dedication.

And I have always liked the White Sox because, well, they have to try harder to earn the fans’ affection. Life isn't fair. The Cubs… everyone likes them, win or lose. The Sox have to earn it. Man, I've come to respect that, and 2005 was quiet vindication.

You're right on Lovie Smith's 2004 Bears, and there's a parallel to the Bulls as well.

In ‘04, the Bears hire Lovie Smith – a very, very good defensive coach. Moreover, Jerry Angelo has a drafting philosophy of choosing players with high floors but not necessarily high ceilings. And, I have to say, early on, he gets a lot right. Lance Briggs, Charles Tillman, Nate Vasher, Chris Harris, Tommie Harris. I mean, seriously, the guy can draft defense! And Lovie can coach defense!

But... the offense? First offensive coordinator Terry Shea? Fired after one season. His replacement Ron Turner? Mediocre. The QBs? Don't get me started. Craig Krenzel and Jonathan Quinn? Disasters.

So while this was going on, the NFL clearly had been evolving as a QB-driven league. Manning and Brady, Kurt Warner, Donovan McNabb, and others rising to fame. And deep down you just knew. You knew that despite these changes, we were still a step or two behind the rest of that league. So that's also when I decided Bag Boy had to be more than just the guy on the barstool, so to speak. The character itself should be jealous and immature, wanting what other cities have, wondering why the Bears can't do what other teams do. He has to wonder why the Packers can go from Brett Favre to Aaron Rogers without skipping a beat while we still have our thumbs up our butt.

You see, what really drives the character and the viewpoint, isn't that Bag Boy has never seen success and is wandering he earth wondering what it feels like. No, the tragedy of Bag Boy is that he has seen it and felt its emotional impact very very deeply. He was in the stands in '85 when the Bears pummeled Washington 45-10, was there when Walter Payton broke Jim Brown's record (and raced home to watch the Cubs lose Game 5 of the NLCS to the Padres. Truly a bizarre day).

He was at the Pontiac Silverdome on Easter Sunday in '88 and saw MJ drop 59 on the Pistons.

So he's seen it and felt it, and is waiting for the stars to line up and these magical events to happen again. And his obsession with this has stunted his growth in other areas. He can't have a serious relationship, he doesn't have a meaningful career… he only exists through the wins and losses of others. Given how much he has given up, he demands and craves excellence in return.

As for the Bulls, they made a similar move. Their move to Skiles was such a Chicago move – get the guy who can get you to at least average to pretty good. Strong, tough-nosed guy, and you know the team will play hard. Chicago always falls for that kind of guy but it seems to have its limits – it still does. In the NBA, you can’t out-coach talent. You couldn't in 2004 and you can’t now.

I guess now I can answer your questions. I think we got the tone of it pretty quickly. And the formula (keeping it simple) was: What happened the last seven days, what's coming up the next seven days? But at this point, I had studied sports for so long that I was beyond watching athletes. I mean, I still enjoy that but I was studying organizations and philosophies and studying drafts etc. so I wanted Bag Boy to really point out the limited thinking and philosophies of Chicago's sports teams.

We'll take the Bears as an example. Since 1985, Chicagoans have collectively fooled themselves that winning a Super Bowl was possible with good special teams and an awesome defense. That stems from 1985. But that's not actually what happened. In ‘85 the Bears had all-pro offensive linemen, a very good QB, and a great running game. It’s just that the defense was so dominant it was mythologized. And that has cost the franchise dearly.

So, as you say, while the Bears ascended under Lovie, were they really headed toward being the best in the NFL? No. And really, only with the hiring of Trestman and Emery and the trade for Cutler have they begun to modernize their franchise.

See, the hardest part about being a Bears fan, and Bag Boy really feels this, is that the team has always given this city tremendous individual players that you loved, and I mean loved with all your heart because the players had such great hearts: Butkus, Sayers, Ditka, Walter Payton, and then Urlacher, and others. But really, look closely. These players have played on some hideous, hideous teams. And because they are Bears and so deeply loved, it masks the fact that the franchise, for most of post-WWII, has been second rate. It really has been. Beloved, but second rate.

So the character had to have a heart, but also an analytical mind that pointed out these “atrocities.”

For some reason, and I have no idea why this is, people respond very strongly to this column or this idea. I was on an improv troupe with a girl who worked sales for RedEye. They were going over demographics and testing etc. and she told me she was in a meeting and this column (concept?) had scored off the charts. So people connect with it – is it because of the length? The ease of reading the column while commuting? I really don't know. But it has always been strongly supported by those within RedEye and those who read RedEye. There's never been an issue of, "Well, this isn't working.” So I've been lucky.

In short, more than anytihng else, I write from the perspective of someone who craves excellence. He sees these seemingly inconsequential midwestern towns, towns like St. Louis who has the Cardinals, or Green Bay who has the Packers, or Detroit who has the Red Wings, and he just cannot believe, can not fathom, how these towns were blessed with greatness (and I mean consistent greatness — year in and year out) and Chicago could have somehow been left out.

HOW IS THAT POSSIBLE? Shouldn't Chicago have gotten a great football franchise? Or shouldn't maybe one of the two baseball franchises have been truly great? These are the things that torment him and they make it easier to write the column because there's an endless supply of bile here.

I'll close with a quick word on hockey. Of course the Blackhawks are great but I have a hard time writing hockey and I'll share why. When I was young, and you're at the very critical age where you star figuring out what's cool, what you like and what you don't like, the Blackhawks disappeared. Their home games vanished form TV, and you really had to go to the games to learn the game. It was just one of those things I was removed from. Not necessarily by choice. And we lived on a pond and I would skate on that pond! But still, no real emotional connection to the sport or the team.

Instead, at that age, the Bears drafted Walter Payton. And that changed everything. Fast forward, early 1990s, I was a radio reporter for a struggling radio network and covered Blackhawks practices and got to know the – but still, it's like I missed my window to really fall in love. And then of course the Hawks really go away again during the (gasp) Alpo Suhonen years.

But, the real lesson there is... with Chicago, you can always always make it back.  It's a very forgiving town with a great heart and that has made this Blackhawks run very fun to follow – though I just don't have the technical knowledge to write with great conviction. I piece it together from what I watch, read, and hear.


There's a lot here to talk about, (especially the idea that the '85 Bears were ultimately harmful to the collective Bears fan mindset), but I want to focus on one area: identity.

While you make the distinction between Bag Boy and yourself, you also regularly conflate Bag Boy's feelings/thoughts/experiences with your own. You say that Bag Boy was in the stands for Bears-Washington in '85 or MJ's 59 on Easter in '88, but of course (and I'm assuming here) that was you in the stands. You say you "have always liked the White Sox," and that seems to be you talking, the actual person... and yet Bag Boy's column this week ended on high praise for the Sox.

So I have a two-part question:

How closely do Bag Boy's views mirror your own? And if it's as close as it seems to be (and it seems completely the same), why not just write the column under your own name? What do you gain (or what does the column gain) from the character and, by extension, the anonymity?


Bag Boy's views mirror my own very closely. The only difference is when I myself would have a logical normal reaction to a situation, I have creative license with Bag Boy to take the absurd negative reaction and run with it. It helps me when I'm dry and can't come up with anything.

Given their similarities, it was decided we would go with Bag Boy as a faceless character as an homage to faceless humor. Think "The Onion" and how you never really know who's behind those funny pieces. We wanted to create that sort of affect where people are going "Who is this guy?"

I believe what the column gains is freedom to really speak the truth about things without it seeming like I'm doing it for my own attention/gratification.

It's almost like a superhero: because no one knows his identity, he's able to play outside the system and make more pointed statements. And it doesn't happen often, but at times we have just gotten silly with it – making all sorts of bizarre lists, suggestions for trades, suggesting the Bears move all of their defensive players to the offensive side of the ball. It's a license for absurdity.

Plus, when he first came out, RedEye was just getting started and needed to establish it's own identity – so maybe there was some push to create some different types of columns. I really don't know…

If it's just me and it's negative all the time, then we have another Steve Rosenbloom, and why do we need another one of those?

Good point on the Sox. I'll elaborate. Bag Boy has a soft spot for the White Sox because they gave him something to be proud of: the 2005 championship. If you study that team, it was such a collection of Chicago-type guys, and no one symbolized that more than Paul Konerko, the consummate “grinder”: quiet, dedicated, produces consistently, gives quiet thoughtful answers to media questions.  So consistent.

Now, the extreme emotional reaction would be to just be irate that he wasn't offered a new deal – that's the cartoon move and within the Bag Boy arsenal. But in this case, and in cases where it's really merited, I like to pause and take a more reflective approach. Now, we all know he's what, 37? Past his prime and not coming back. A rant isn't what I was feeling. What I really wanted to say was, “Hey man, you played almost your entire career here.  You didn’t take the money and run. You gave the World Series ball to Reinsdorf. You were a quiet, dedicated leader for a very long time. Thank you for that service – thank you for being so real.”

I tried to express that because players like him really don't come around that often. So many are fake, marketing-driven, tweeting this or that.  He was different. I don't think he ever had a twitter feed or any endorsements I could think of. How rare is that?

Bag Boy also likes the Sox because they have to earn their fans’ respect and devotion –there is a quiet dignity to how they go about their work, which I admire. Bag Boy does too, but he got impatient with the Ozzie/Kenny fiasco.


Very interesting, and makes a lot of sense.

I want to wrap it up, just because we're already at a pretty substantial read. So I've got just two more areas of discussion.

First, you mentioned not wanting the column to be in the vein of "another Steve Rosenbloom." Who are Bag Boy's favorite Chicago sportswriters, particularly sports columnists? Past or present.

Lastly, you've said that part of Bag Boy's character comes from not seeing the requisite outrage from Chicago fans over certain fundamental failures, such as the Cubs attempting to be "loveable losers" despite being a big market money maker, or the Bears embracing an "all we care about is defense" attitude fostered by the '85 team that actually was a terrific offensive power.

With all that in mind, do you think there is an emotion that is most prevalent in the Chicago sports fan mindset? And if so, what kind of effect does that emotion have on our interactions with our teams?


Wow. That last question, more than any other, gets right to the heart of the column.

1. I didn't have a ton of influences as far as sportswriters growing up. I recall liking Mike Royko a lot, and then I really got hooked on Bernie Lincicome – I thought he was really funny and interesting.

No, my influences were more comedic – I grew up watching Belushi, Aykroyd, and Murray on SNL, and thinking to myself that no matter what, I really wanted to be that funny and charismatic.

As I grew up, Chicago really was the best media town in the country. It really was. We had two very strong papers (three before the Chicago Daily News folded) and fantastic local news coverage. The people on TV were reporters and journalists first, TV personalities second. I remember watching Bill Kurtis and Walter Jacobson on Channel 2. These were great newscasts to watch, and remember, there were only a handful of channels back then so people made it a point to sit down and watch both the 5 pm and 10:00 newscasts. It seems so hard to believe now. Mark Giangreco was and is a huge influence – I interned with him and it was a fantastic experience. A very strong writer, and very funny as well. I remember watching him and realizing that yes, it is important to develop style in the work that you do. There's nothing wrong with that.

More than that, Chicago just seemed to me to be this mecca of passionate, smart, engaging personalities. I'll always remember the laughter.  I'll always remember the Loop, AM 1000. You could listen to Jonathan Brandmeier in the morning, Kevin Matthews midday, Steve and Garry afternoons, and Chet Coppock did an evening sports call-in show long before anyone else was doing it. Now that was a line up! Bruce Wolf's sportscasts influenced me as well — he seems smart enough not to take any of sports that seriously.

So it's a mixture of comedy and media influences.

2. This is a really hard question because I believe the mindsets are different depending on the team.  If you're a Cub fan, the overarching emotion is a sort of "woe is me" attitude that they all secretly love… sort of an "I don't know what the next awful thing is going to be but I can't wait to find out!" It's like they're addicted to it.

Sox fans have more jealousy/envy just because no matter what, even if they win five World Series titles in a row, they'll never be loved like the Cubs. Never. Even their stadium, which is actually quite nice by anyone's standards, will always fail in comparison to Wrigley Field.

Bears fans? I think pride. Just very proud of the history, of being the charter franchise of the NFL, of knowing that our founder was instrumental in developing the league and one of the pioneers in revenue sharing, of having a legion of Hall Of Fame players, of having this unique football setting against a gorgeous skyline and lakefront. I often wonder what national audiences think when they see that. Because I see it every week and I still can't believe how beautiful the skyline is.

Blackhawks fans are just giddy. They're enjoying a tremendous renaissance and all of the national attention and the fact that the core is so young. They're going to be here for 10-15 years. It's too good to be true.

And of course Bulls fans? Hope. Lots of hope, because you have the one key piece, the anchor, the heart and soul of the team. Now it's a question of getting just a bit more luck and finding just a few more key guys. They can smell it, they know it's out there, and it may be just a mater of time.

ED. NOTE: We concluded this interview three weeks before Derrick Rose was lost for the season… again:

But the one overriding emotion is probably… fear.  Fear of not being the best, fear of being left behind in national discussions, fear of being forgotten by the East Coast media, fear of being the second city forever, fear of injuries, bad trades, bad management, bad ownership, bad coaches. There's so much fear. If you ever read an internet piece, read the comments after it. It's just insanity. “Cutler isn't this,” “Cutler will never be this,” “the Bears will never be this or that as long as the McCaskeys own them,” “the Cubs will never be this because of that”… just naysayers everywhere.

It comes from a long history of under-performance across the board. But as you said, 2004 marked a real resurgence where every team is at least relevant – is at least in the hunt, is at least trying to create a sustainable, winning culture, not just at the field level, but in terms of scouting and drafting and developing players. You can see it and feel it – that these teams are waking up and starting to "get it." The results aren't there yet – it takes years – but the Cubs are doing what needs to be done, and the Bears are doing what needs to be done, and the rest already have started.

It's a very exciting time for Chicago sports, and I'm proud to cover it, albeit in a very different way. Thank you for letting me share some of this.

As a side note, are you a Sopranos guy? If so, you may remember Tony, after an intense therapy session, saying to Dr. Melfi, “Sometimes what we do here feels like taking a shit!”

Melfi: “I prefer to think of it as giving birth.”

Tony: “No, it's like taking a shit.”

Whatever this was, birth or shit, it's been clarifying for me as well.




Jack M Silverstein is the founder of Eye On Chi, and a staff writer for the Chicago Daily Law Bulletin. He is also a regular contributor to RedEye, where he and Bag Boy have shared a page on many a Friday. Say hey @readjack.

Bag Boy is a RedEye special contributor, whose column appears every Friday.

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