Rick Pitino had never seen anything like it—the “negativity” that pervaded Boston sports.

It was March 2000, and the 47-year-old Slick Rick was CEO, president, general manager, and head coach of the Boston Celtics…and they were awful. With pressure mounting from media and fans alike, Pitino snapped after a particularly heartbreaking loss:

“All the negativity that’s in this town sucks….I’ve been around when Jim Rice was booed. I’ve been around when Yastrzemski was booed. And it stinks. It makes the greatest town, greatest city in the world, lousy.”

It’s become a calling card—a point of pride, even—in Boston: We’re tough on our athletes, and the ones truly deserving of praise will play better because of it. None of this is to say, of course, that the rest of the nation’s great cities take a rational approach to sports. Hell, fans in Philadelphia cheered when Joakim Noah injured his ankle.

And then there’s Chicago, where the talk-radio blowhards blow so hard that SNL paid homage with the long-running “Bill Swerski’s Superfans.”

So with Theo running the Cubs and with Kevin Youkilis moving from Boston to Chicago, we decided to pose the question: Which city’s teams have it worse when it comes to media? The Hub, or the Hub of the Midwest?

In pursuit of an answer, ChicagoSide brought together veteran sports writers Steve Buckley of the Boston Herald and Laurence Holmes of CBS Chicago for an electronic conversation.

Q: Which city’s sports media is worse, Boston or Chicago? I know “worse” is a subjective term, but here it means nastier, louder, more aggressive.

STEVE BUCKLEY: Boston’s media is “worse” in terms of how the question was posed. The thing is, it’s not as “worse” as it used to be. We don’t have as many pure columnists as we once we did, and fewer columnists means fewer opinions—opinions that might land hard on the toes of sensitive players, owners, front-office types, etc. Consider that last fall Red Sox principal owner John W. Henry charged into the studio of one of Boston’s sports stations to argue—on air—about what was being said about him that day. He’s received so little critical media coverage in Boston that all it takes is two whiny guys one afternoon drive to set him off. The talk shows do a better job of being critical (read: negative) than the newspapers do, though a good chunk of it is rotating hosts and callers beating the same issue to death for 12 hours.

LAURENCE HOLMES: I think both cities are very passionate about their teams, and the coverage is hard in both. What I find interesting is what each town is passionate about. Chicago is Bears-centric. It’s weird to me that any town with a football team wouldn’t be NFL-centric, but Boston is that way. A Red Sox title means a lot more than a Pats Superbowl. Here, the Superbowl is the Holy Grail because the city is divided between baseball teams.

Q: Who can forget Rick Pitino’s rant? “All the negativity in this town sucks….” Say what you will of Pitino (and there’s plenty to say), but did he have a point? How about in Chicago?

BUCKLEY: No, he did not have a point. Not even close. He did a poor job with the Celtics, and people (fans and media) called him on it, and then he turned around and said everyone was being negative. It’s times like these that I like to pull out an old line from Bill Ballou, who for many years has covered the Red Sox for the Worcester Telegram: “When they play bad, I write bad.” In other words, is it being negative if you’re being critical of an under-performing team?

HOLMES: Saying that the media is “negative” is a cop out. Ask anyone involved in sports media coverage and they’ll tell you that it’s better for everyone involved when the teams do well. That drives readership, viewership, and listenership. Quite frankly it’s more interesting to talk about a team that is winning. I know it’s more enjoyable for me to talk to listeners who are truly engaged in the team rather than listening in to see how I’m going to rip them.

Q: Bill Russell lamented in 2009 that there’s too much opinion in sports coverage nowadays, not enough reporting. Agree?

BUCKLEY: Bill Russell: The greatest athlete in Boston sports history. And to argue otherwise would be, in the words of the late, great New York barkeep Toots Shor, advertising your ignorance. He played 13 seasons with the Celtics. During that period, the Celtics won 11 championships. To quote another great saloonkeeper from back in the day, Boston’s Michael McGreevey: “Nuf’ ced.”

Now that we have all that out of the way, Bill is wrong.What he fails to grasp is that there were a lot of opinions flying around about the Celtics back when he was playing, except that these opinions were being shaped at Joe Hart’s in Cambridge, Malachy’s Saloon in Quincy, the Jumbo in Somerville … and, you know, other places where men drank beer and talked sports. (I’d be remiss if I didn’t mention one of my dad’s old haunts, the suitably named Inman Square Men’s Bar in Cambridge, with its flashing neon “Ladies Invited” sign.) Sports bars have become silly little theme parks now, and the hard-edged sports talk has moved to the talk shows and Internet blogs. I presume that’s what Bill Russell is hearing and seeing.

As for reporting, it’s either better than ever or at an all-time low—it changes from minute to minute. It’s better than ever when one considers that I can get an update on a trade rumor just by looking at the Twitter feed on my cell phone. But then (and here’s the minute-to-minute part) it’s at an all-time low when it turns out that the reporter had it all wrong but rushed his nugget of misinformation into the laps of his Twitter followers because of an obsession with beating the competition by 35 seconds.

HOLMES: If the opinion is based in fact, I have no problem with it. What I do have an issue with is people who present an opinion to incite, instead of trying to have in-depth conversation on the matter.

Q: What impact do you think sports media can have on the decision-making process of a general manager? There was a fairly loud contingent calling for Kevin Youkilis’ ouster. Do you think GMs begin to hear that?

BUCKLEY: Way, way overstated. The “fairly loud contingent” calling for Kevin Youkilis’ ouster was coming from the clubhouse, not the pressbox. And, anyway, I was hoping the Red Sox could find a way to keep Youkilis. The guy plays every inning of every game of every season as thought it’s the bottom of the ninth inning of Game 7 of the World Series, and, what, people want to run him out of town? And why? Because he throws his helmet, frowns a lot, and may or may not have been the guy who told a reporter that the starting pitchers spent the last month of last season on in-game beer-and-chicken feasts? Weird: They fired manager Terry Francona and they gave away Youkilis for 10 cents on the dollar and they kept all the starting pitchers, who still suck.

HOLMES: They listen. They hear it, but they’re not going to make a move just because of pressure. The interesting thing that teams don’t always understand is that some of that opinion isn’t just driven by emotion. I might have a conversation with a person inside the organization who floats the idea.

Q: I think it’s fair to say the fans and sports media in both Chicago and Boston are loud and opinionated. Who’s the chicken, and who’s the egg in that scenario? Do the fans demand that kind of coverage, or does the media incite the fans?

BUCKLEY: Hmmm … good one. Gotta go with the media giving the fans want they want. Talk-show hosts who begin their tenures with promises of “raising the bar” and offering “intelligent sports talk” are soon beginning an exciting new career as the delivery man who drops off the Popeye’s chicken at the Red Sox’ clubhouse. The guys who do a lot screaming and finger pointing, and who can add a little Joe McCarthy to the mix (“I have a list of 10 steroids users in my pocket”) generally get the higher ratings.

HOLMES: Our job is to reflect and inform. I think our consumers are a lot smarter than they are given credit for. As sports radio grew, you saw a lot of the “loud-mouth” hosts disappear. Remember, only 2 percent of our listeners ever call in. It’s OK to be passionate, but no one wants to hear someone screaming into the mic all the time.

Q: Do you both take comfort in — “Hey, at least we’re not Philadelphia”? I mean, those guys booed Santa.

BUCKLEY: No, I love Philly. And they didn’t boo Santa — they booed a badly dressed, amateur Santa knockoff. The Eagles were having an awful season, it was a cold day, and now this homeless Santa was waddling onto the stage. Fans in Boston and Chicago would have booed him, too. The only difference is that the teams in Boston and Chicago win now and then. But love the passion.

HOLMES: It does bother me a bit that there are those that revel in that. There are places in Philly where they actively say, “We don’t want out of towners in our establishment.” You see pockets of it popping up all over the country. I am encouraged by the fact that, when in Green Bay, Detroit and Minnesota, there’s been a higher level of civility than I expected.

Q: Let’s wrap this all up with this question: If you were Kevin Youkilis (and in a hypothetical world, your only concern was how fair and balanced the sports coverage in a city is), where would you prefer to play? Boston or Chicago?

BUCKLEY: Kevin Youkilis loved Boston. He was one of the few Red Sox players who lived in Boston during the off-season. He went to Celtics games. He palled around with Bruins tough guy Shawn Thornton. He did charity work. A couple of years ago, I wrote a column exploring Youk’s passion for Boston. Here’s an excerpt:

“Youkilis has evolved into a year-round resident of Greater Boston, a guy who knows that the South End and South Boston are different places, someone who can climb behind the wheel of a car and travel from Fenway to Fairhaven without making an improbable pass through Framingham.

He is, in short, one of us. And guess what: He has every intention of remaining one of us.

‘I see myself, if everything goes well, retiring as a member of the Red Sox,’ said Youkilis earlier this week, following a morning round of batting practice at the team’s minor-league complex in Fort Myers. ‘That’s my goal. I want to finish my career with the Red Sox, and that’s not something that a lot of players do.’”

OK, so the finish-my-career in Boston thing hasn’t worked out so well, unless the Red Sox, ever on the alert for a cheap marketing stunt, sign him to one of those phony-baloney one-day contracts when he retires. But he’ll always be “Yoooooook” in Boston. In Chicago, he’s just a guy passing through town.

HOLMES: I don’t think we have to be hypothetical. Youkilis has already gone on the record saying how much he enjoys Chicago. As I said earlier, with Boston being so hungry for Red Sox news it makes sense why it would be less comfortable for a player. Plus, just from the clubhouse standpoint, there’s much more space on the South Side of Chicago.

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LIAM MARTIN, Beantown native, is a reporter for WCVB NewsCenter 5 in Boston. Liam also spent some quality time in Chicago—he received his master’s in journalism from Northwestern University. Follow him @LiamWCVB.

STORY ART: Main image made in-house with photo by Charles Krupa/AP Photo.