For those who don’t know me, my name is Reid Rooney, and I am the CEO of Betsperts Media and Technology Group – the company that acquired Bleacher Nation a few years back.
Apologies up front, but this is going to be a long article. And it will be from my perspective, which is fairly unique based on my personal and professional history with Chicago sports and the sports media industry in this city. I encourage you to read with an open mind (remembering that I am not a writer by trade), because it felt imperative to say something in defense of all Chicago sports fans and against the way Jerry Reinsdorf has treated his two teams and the rest of sports fans in this city.
I am 99% sure that either Jerry or his team will read this, so feel free to drop a thoughtful comment without crossing any lines. You never know what might stick.
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Nearly two decades ago, Bleacher Nation began as a small Chicago Cubs blog, but today, it’s the largest Chicago sports website in the world, with the two most widely-read Chicago Cubs writers in the industry. The irony of my leading the group that bought BN is that I absolutely despise the Cubs. And that’s because I love the White Sox more than anything in my life outside of my family. I hate myself for it … but I can’t help it. They’re my team. They’ll always be my team. I haven’t (and I won’t) let Jerry Reinsdorf take my team from me.
Maybe the most ironic part of this particular endeavor is that the final straw that made me start typing was Reinsdorf reportedly talking shit about the Cubs to the Brewers last week, as reported on ESPN1000. I promise this isn’t a White Sox article …. This is about the legacy of one of the worst non-criminal owners in the history of all of American sports.
I will get to it now.
© Orlando Ramirez-Imagn ImagesJerry Reinsdorf: The Positives?
Although I say (and believe) that Jerry is one of the worst owners in the history of American sports, he does deserve some credit before I, as a fan of the teams he runs, bash his legacy.
Obviously, Jerry was brilliant for buying both the Chicago Bulls and White Sox when he did. Admittedly, his responsibility (at least early in his ownership) was to earn money for the ownership group that helped fund those purchases. He absolutely has done that. Though perhaps not to the extent he could have, which is kind of my point. But he has made lucrative deals with the city and state, and has owned the team long enough to return profits that investment groups can only dream of.
But that’s not all Jerry Reinsdorf deserves credit for.
“He also deserves credit” for not breaking up the Bulls dynasty and pushing out the greatest player and arguably the greatest coach in the history of the sport … earlier than he did.
“He deserves credit” for the amount of power he gained amongst owners in the MLB while leading a lockout when his White Sox team was one of the favorites to win the World Series. He chose money over a potential World Series. His investment group must be so proud.
“He deserves credit” for Frank Thomas’ MVP in 1994; for leading the fight against the strike that shortened the season when Frank had a .353 BA, 38 HRs, 101 RBIs, .729 SLG, and 1.217 OPS. After all, Frank had 49 (yes, 49!!!) games left and could have gotten hurt or slumped and lost the MVP. What a genius.
A bit more serious, he deserves credit for the deal he swindled Chicago into for a new stadium. 30+ years ago, Jerry Reinsdorf was one hell of a negotiator, and used a potential relocation to St. Pete to get the city of Chicago to essentially encourage him not to spend to win, but to maximize profits by “finishing second or third” with lower payroll and not paying the ISFA ticket fees.
Even though he negotiated one of the greatest stadium deals in the history of sports, sadly for his investors, he didn’t have the foresight to maximize profits by getting the stadium built in the South Loop that would have increased the value of the franchise significantly.
He deserves credit for winning the 2005 World Series. They led wire-to-wire in the regular season and went 11-1 in the postseason. They may be the single greatest team in American professional sports *that no one outside of this city remembers or talks about.*There you go, Jerry, there is your credit.
© Kamil Krzaczynski-Imagn ImagesJerry Reinsdorf: Uniting a Divided City
As I mentioned, the Sox are my team. They are my single biggest passion in life. My dad and grandpa have had season tickets to the White Sox for over 40 years. I watched 130+ games of the worst team in the history of baseball in 2024. Sometimes, the life of fandom feels more like an addiction than a choice.
But the Sox are only one of Reinsdorf’s teams (and sins). There’s also the Bulls.
My wife and I are currently on vacation in Europe. When we were in Istanbul, I saw Bulls jerseys, Bulls hats, and Bulls hoodies all over the city. STILL to this day. That is arguably despite Reinsdorf’s best efforts to destroy one of the previously most beloved global brands.
For those who are old enough to have enjoyed the 90s and gone to a Bulls game … have you had many better sports or entertainment experiences in your life? When we got lucky winning the lottery for Derrick Rose (and we had the rivalry with the Cavs), was there a better arena in the country to be in?
But now … Is there a single kid in Europe or Asia who has intentionally watched a Bulls game for the last decade? Hell. You can almost ask that about kids in Chicago. The Bulls are (and should be) an INCREDIBLE profit machine. Other owners have to be immensely jealous. Instead of proudly stewarding that brand, he has minimized the value of his organization by worrying more about short-term dollars in the door rather than being one of the biggest global basketball brands in the world. He had that chance. He picked “Play-in game ambition” instead.
From a passionate fan’s perspective, from an owner of a business that has insanely more Chicago sports traffic than Jerry’s streaming channel, I can guarantee you that Jerry Reinsdorf has close to (if not) the lowest approval rating in the entire city of Chicago.
Here’s what Jerry has missed in his last 25 years, in my opinion: Chicago fans ultimately don’t care whether you win or lose IF we can tell that you are making an honest effort to try. That is how desperate we are after the failures of the last 50 years. We just want you to care as much as we care.
Chicago is one of the greatest cities in the world. We have some of the best fans in the world. I don’t say that lightly….
Look at how the city supported the Blackhawks when they started to care about fans when Rocky took over. Look at how the city supports the Bears, who have been mismanaged for decades, but occasionally demonstrate a legitimate desire to win.
Look at the Sox in the World Series or the blackout game. Look at the Hawks and Bulls fans in the ’90s. Look at the Hawks fans in the 2010s. Look at Cubs fans in 2016.
And most recently, look at Cubs fans, who just last week showed up BIG for Games 3 and 4 of the NLDS against Milwaukee, even after ownership claimed “biblical losses”, noted that they were just “trying to break even”, and reminding folks that they “spent a billion in and around the stadium” … even though they’ve made much more in value since then. To say nothing of what they haven’t done in free agency, relative to their financial might.
The fans hope that, at some point after turning a $30M investment into ~$10B, Jerry Reinsdorf might have considered putting us first.Here’s the other thing Jerry continues to miss: Not only would the value of his teams and organizations grow if they won (looking at Golden State before Steph and now), but also, after he made enough money, he could have been one of the most influential people in the city. JERRY could have provided happiness and family memories to people. Instead, he continues to pick the lesser certain small profits versus the bigger prize in both money and influence.
© Kamil Krzaczynski-Imagn ImagesJerry Reinsdorf has owned the Chicago White Sox for 44 years now. In those 44 years, he has led the White Sox to win a playoff series in EXACTLY 1 SEASON. This is not a misprint. We (yes, I said we) went 11-1 in 2005 … and HAVE NEVER WON A SINGLE PLAYOFF SERIES IN ANY OTHER YEAR OF HIS OWNERSHIP.
Jerry – That is absurdly unacceptable. In those 44 years, you could have provided fathers, mothers, sons, daughters, friends, partners … any Chicagoans … some of the happiest times of their lives. Instead, you went the other way. And you don’t seem to realize – or care – that your legacy is cemented. It’s too late.
Based on recent stadium negotiations and soft threats to leave, which have been hysterically shot down by the commissioner, you still think you have control. You don’t.
Based on the massive failure of taking the games to air via a private streaming company …
Based on having the worst team in the history of baseball following the year you laughed at the end of the season interview (with only select reporters invited)…
Based on being voted the worst organization in the NBA over and over again…
Based on not being able to convince government officials to give you a sweetheart deal again…
Based on any opinion from 99.9% of fans in Chicago (the 0.1% being from the ones who think you actually drafted MJ)…
Based on every radio show, newspaper, influencer, blogger, writer, podcast host, YouTube channel … on literally all of the evidence …
You have lost. Yeah, maybe you’ll laugh your way to the bank using $100 bills to light your cigars, but that won’t be your legacy. You are literally the only thing that unites Chicago. In fact, it’s kind of refreshing in this divided world that we all have one opinion in common… the collective opinion of sports owner Jerry Reinsdorf.
Your legacy will be laughing at fans because you know better. Your legacy will be that you broke up one of the most important dynasties in sports. Your legacy will be that you refused to give Manny Machado the deal you promised to support, which led to not even trying for Bryce Harper. Your legacy will be hiring your friend and still defending it while everyone in baseball (including in your organization) laughed at you, not with you.
Your legacy will be that you made it more difficult to watch and support two of the worst organizations in sports. Your legacy will be that you choose your net worth over the people who would bleed for a single playoff series win.
Your legacy will be NBA Play-in games. Your legacy will be me, my dad, my brother, my grandpa, my cousins, and every other Sox fan not having enough moments to talk about, pictures to look at, or memories to reflect on. No beers to cheer. No tears of happiness or celebratory hugs.
Your legacy will be that you are one of the last two owners who have still not given out even a $100M contract. Your legacy will be laughing publicly, thinking Shohei Ohtani is overpaid. Your legacy will be a disappointed Pope (educated guess). Your legacy will ultimately be a mountain of sadness that makes the billions you made look like an ant hill.
Your legacy will be proven almost immediately after Matt Ishbia takes over the team, because the world will see White Sox fans once someone finally cares like we care.Jerry, even if you authentically tried just once, you could have changed your story. All you had to do was have this mentality…
Phoenix Suns owner Mat Ishbia’s full response when I asked him about Stephen A Smith’s notion that he’s “on the verge of becoming the worst team owner in sports history.”Video credit to @azfamily pic.twitter.com/6rNrI5jkZj
— Shane Young (@YoungNBA) April 17, 2025…and we would have forgiven and supported you. Now, it is too late.Jerry has had 44 years to help Chicago win.
In 43 of those years, he failed to maximize the money put in the pockets of bartenders across the city, to pay police or security for more playoff games, to have sponsors pay TV channels, podcasts, and websites for increased traffic, to bring in more taxes for the city and the state.
In 43 of those years, he has failed to give part-time workers more jobs, to hand significant playoff shares/bonuses, to bring hundreds of millions of dollars into the economy of Chicago, to help families create lifelong memories … or simply to distract us from the pains of real life just for a few extra days.
He has had 44 years to realize some Sox fans’ biggest rival might be the Cubs, but all of us (and Bulls fans) have the same common disappointment, sadness, lack of hope, and real rival … Jerry Reinsdorf.
So, Why Write This Today? Because of What He Said About the Cubs
According to some reports, Chicago has held five of the largest attended championship parades in American history, with the Cubs (2016) being the largest. The Sox (2005) and Hawks (2013) are in the top 5, and the Bulls (1991 and 1998) are in the top ten. Chicago shows up. Chicago will always show up.Earlier this week on ESPN 1000, we learned that Jerry Reinsdorf spoke to people in the Brewers organization, encouraging them to beat the hell out of the Cubs. It was also reported that during the 2005 World Series, Jerry said to a radio host, “How did the Cubs do today?”
This is the final straw for me.
As a huge Sox fan, I understand and fully support Sox fans cheering against the Cubs (until we bought Bleacher Nation), but here’s what I have to say after hearing Jerry’s comments.
Jerry – How did you do today?
The Cubs brought people to the bars and restaurants for the last month. The Cubs got parking attendants paid. The Cubs got Barstool Big Cat to win $100k in 50/50, which he gave to a charity helping the youth on the South Side. The Cubs WON a playoff series this year. The Cubs may have lost Game 5 last weekend, but I guarantee the memories from Game 3 and Game 4 will be cherished.The Cubs made Chicago special for the last month. The Cubs made Chicago the best city in the world Thursday night. The Cubs made fans shed tears of happiness. The Cubs made fans lose their voices. The Cubs created framed pictures on walls. The Cubs created one of the greatest moments of Ian Happ’s life. The Cubs made waking up on Friday morning better. The Cubs made their fans forget pain and struggle for a short period of time. The Cubs created a legacy moment. The Cubs gave hope. The Cubs gave relief. The Cubs gave belief.
What did I get, as a Sox fan? I spent my time looking at Arizona Fall League stat lines. I checked prospect rankings. I read a 2026 mock draft. I searched for information on the draft lottery. I went back and looked at a picture of my dad, my brother, my grandpa, and me in 2005 at the World Series, because we never got to go to another playoff game together.
Chicago shows up. I will show up. I will be at the season opener. I will cheer. I will watch. Not because of you, but despite you.
You have failed Chicago. That is your legacy.
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