Goodbye Pirates: I Am Jumping Ship To The Cubs

By January 22, 2018April 2nd, 2019No Comments
goodbye pirates

On the heels of the Pittsburgh Pirates trading Gerrit Cole and Andrew McCutchen, plus having an ownership group (lead by Bob Nutting) that gives zero craps about their fans and will not do what it takes to win a World Series (despite what they want you to believe), I am declaring that I am boycotting the Pirates and will be giving my attention and dollars to the Chicago Cubs.

This is a decision I do not take lightly and is one that is likely to draw the ire of many.

Let’s start at the beginning.

pittsburgh sports podcast

I grew up in Pittsburgh and am a yinzer that bleeds black and gold. As a kid who was born in 1980 my first sports love was the Pittsburgh Pirates, starting with the 1987 season. My fandom went to a whole new level with the back to back to back NLCS appearances in 90-92. They had the killer B’s of Bonds* & Bonilla (I still have a Bobby Bonilla poster hanging up in my man cave), Andy Van Slyke (greatest crow hop ever), Chico Lind, and Spanky LaValliere. Life was great and as an impressionable 10 to 12 year old I found my first love (actually, it was a co-love because at the same time Mario Lemieux and Jaromir Jagr were lighting the lamp and winning back to back Stanley Cups.) The Steelers, who were trotting out Mark Malone and Bubby Brister at quarterback, were a distance third.

Then the unthinkable happened and MVP Barry Bonds* left the Pirates for the Giants and so began the longest streak of consecutive losing season in American professional sports history. This lasted twenty long and torturous seasons. The team that was once my number one was now the worst team in all of sports…ever.

When this happened I went from loving, to caring, to hoping, to praying, to frustration, to indifference, to anger. I watched as the Pirates putrid ownership and awful front office continually botched high draft picks (Bobby Bradley, Bryan Bullington) while shipping off the only talent we had (Brian Giles, Jason Bay) for fifty cents on the dollar. They continually preached patience and getting younger yet year after year nothing changed.

On numerous occasions, when the losing streak reached double digit seasons, I threatened to quit rooting for the Pirates (thanks to Facebook Memories for the yearly reminders.) It made no sense to me why I would show support for an ownership group that clearly didn’t care about putting a winning product on the field. Their actions spoke louder than their words.

Despite my threats I never pulled the trigger. After the first month of every season the Pirates were already out of contention so I was free to enjoy my summer, focus on my fantasy baseball teams as a way to stay connected to the sport, and get ready for Steelers training camp.

It wasn’t until the 2012 season that there was a small glimmer of hope and it came in the form of Andrew McCutchen. It was his third season in the league, he was the Pirates All-Star, and the team finished just four games under .500, the closest they had been since 1997 (yes, it took 15 years to get within 4 games of .500.)

The following season (which I purchased the MLB Extra Innings package for the first time so I could watch the Pirates) Cutch made his mark on Pittsburgh as he burst onto the season hitting .327, with 31 HR’s, 96 RBI and in the process going to his second All-Star game, winning a Gold Glove, Silver Slugger, and finishing third in MVP voting. More importantly the Pirates not only broke their consecutive seasons losing streak, but they won 94 games, made the playoffs (I was at the clinching game in Chicago), and gave me the greatest moment of my Pittsburgh Pirates rooting life, a win over the Cincinnati Reds in the Wild Card game which was capped off by a moment that still gives me chills to this day.

I felt like a kid opening up a pair of Jordan 4’s, a Nintendo, and a Hornets Starter jacket on Christmas. It was a feeling that I had dreamed of for so long. One in which I loved the Pirates and the Pirates loved me back.

I need to make an important note that’ll frame the rest of this story. I have lived in Chicago since 2006. This city has always had a special place in my heart as my Mom’s side of the family is from the Chicago suburbs and I have celebrated Christmas in Chicago every year of my life. It is because of my love of Michael Jordan combined with being raised in Pittsburgh that I am such a sports fan.

It is also worth mentioning that when I moved to Chicago I put my name on the Chicago Cubs season ticket wait list (which is a 15+ year wait) and even purchased a 14-game partial season ticket package for a year (with the goal of making money, which ended up being a bad idea because the team wasn’t good and no one wanted to go see a game on a Tuesday at 2 pm in May vs the Phillies.)

While living in Chicago I made it very clear. All Pittsburgh sports teams are my number one, Chicago sports teams are my number two. Since I create sports content for a living it is always in my best interest for Chicago sports teams to do well since I get to experience and cover it. Plus, Chicago sports are on TV everywhere and I watch more Chicago sports than any team not from Pittsburgh.

This brings us to the 2015 NL Wild Card game where the Cubs, who after a long stretch of their own crappiness, were finally on the rise and have made the playoffs. They are taking on the Pirates in Pittsburgh, who have made the playoffs for the third consecutive season having won 98 games (their most since 1991.) Since I already mentioned that Pittsburgh sports teams are my number one there was no question who I was rooting for, the Pirates.

Unfortunately Jake Arrieta was unhittable that game (and season) and the Pirates lost 1-0. To this day that is the only game of my any consequence between the Pirates and Cubs in my lifetime.

I bring this up because one of the common objections to me rooting for the Cubs and Pirates is, “How can you do that? They are rivals in the same division.” To this I say that neither team has been good at the same time except for this one Wild Card game. The Cubs didn’t start playing in the NL Central until 1994 and the Pirates were a dumpster fire until 2013. No rivalry exists between these two teams. They are more like Craigslist roommates. Sure they face each other in the regular season, but with 162 games the magnitude of each game is miniscule.

Let’s keep the 2015 Cubs season going because it is when an important part of my Cubs fandom started to blossom. The Cubs made it to the NLCS and the city is bursting with excitement. Through my man G-Hunt I was able to get a pass to the owners reception before Game 3 where I was able to meet the Cubs owner Tom Ricketts. He was super cool and personable and even told us about this stud catcher they had in the minors named Willson Contrares, who was going to be a big piece of the team’s future.

bacon sports tom ricketts

Since this day I have met Tom Ricketts one other time and he was just as awesome. This is an important thing to note for the rest of this story as the biggest reason for my exodus from the Pirates is because of their ownership. Tom Ricketts bought me several beers whereas the Pirates ownership traded my beers for the future rights to New Coke.


The Cubs didn’t win the World Series that year but momentum was building and they were one of the favorites in 2016.

From the first pitch of the year Cubs fans were buzzing about what could be the season that breaks the curse. Staying true to the momentum they had built, the team was straight fire all season to the tune of a Major League best 103 wins. They were like if Andre Dawson and Greg Maddux had a baby as they won the NL Central by 17.5 games over the Cardinals.

The Pirates, coming off the three best seasons of the last 23 years of my life, finished 78-83 and 25 games out of first place. Instead of seeing their window to go all in and try and win a World Series by signing or trading for players that could help them get to the next level (at the expense of trading away talent in the farm system and adding payroll), the ownership had other plans. Those plans resulted in the team going in the complete opposite direction and getting significantly worse (to the tune of 20 games worse.) The pitching staff they trotted out that season was (insert Charles Barkley voice) TURRIBLE and not in the stratosphere of what you would expect from a contending team.

I still watched a large majority of the Pirates games on MLB Extra Innings as I fully believed in the team, despite my disappointment with the outcome of the season. At the same time I was also watching a crazy amount of Cubs games (thanks to a second TV and a desire to watch the best team in baseball, something I had never experienced before.)

Now it’s on to the playoffs and the Cubs are favored to win. The buildup and overcoming adversity moments of the playoff run took things to DEFCON levels for Cubs fans. They were drinking the Kool-Aid and were ready to go bananas.

chicago cubs -canhead

While the playoff run was happening I was rooting for the Cubs to win it all for the opportunity to experience history. Something that if it happened I would be telling my grandkids about. Something that would be the biggest party the city had ever seen and would be so much fun. Something that would be on my sports resume forever.

With the best General Manager at the helm in Theo Epstein, the best Manager in Joe Madden in the dugout (I love how positively quirky he is), plus a young squad of mashers and top flight pitching, the Cubs won the World Series for the first time in 108 years.

cubs win world series

HOLY SMOKES WAS IT AMAZING! (we captured a ton of the experience on our YouTube channel!)

At this time I never claimed to be a Cubs die hard nor was I a fair weather fan. I was a transplant who loved sports, experiencing awesomeness, who had followed and rooted for the Cubs for 10 years. I had the time of my life.

If you want to hear stories about what went down in the Wrigleyville epicenter celebration then listen to this episode of the Sports Marketing Huddle podcast that I recorded the morning after the Cubs won the World Series (on little sleep.)

cubs win world series

This picture of three of my friends sums it all up. Who wouldn’t want to be part of that?

Now on to the 2017 season and even though I had just experience a World Series celebration with the Cubs, I was still excited about the Pirates season. I believed that 2016 was the outlier and that the organization that had won 98 games and had been to the playoffs three out of the last four seasons would be back.

Then the season kicks off with Starling Marte getting suspended and Jung Ho Kang getting arrested for DUI. Right out of the gate I knew this team was in trouble, especially considering they made no major moves to upgrade positions. Then Gerrit Cole had his worst season of his career and the season was toast. The Pirates finished 75-87, 17 games behind the first place Cubs.

andrew mccutchen jersey

While this was going on there were rumors of the team trading Andrew McCutchen, something that I was never a fan of. Despite being a die hard sports fan I consider myself pragmatic at how I see things. Even though Cutch may have the most value on the team, and the ownership doesn’t want to pay him on his next contract (which makes logical sense given his age and the fact that the Pirates are a small market team so they can’t afford to spend so much on a declining Superstar) I was against trading him. Thankfully, despite their Mr. Burns-ness, the front office didn’t pull the trigger and Cutch stayed a Pirate. I still believed that the team could succeed given the right pieces (an outfield of Cutch, Marte, and Polanco is one of the best in baseball and with a “hopefully back to his normal self” Gerrit Cole, you’ve got the foundation.)

As for the Cubs in 2017, they continued to be one of the best teams in baseball. I continued to watch more and more of their games, and I truly believed they could have won again last year. Unfortunately once they got to the playoffs their bats and pitching disappeared on them. When that happens you aren’t gonna win.

Now it’s the start of 2018 and the countdown to pitchers and catchers reporting is starting to pop up. To help get the year started off the Pirates ownership and front office thought that it would be a great idea to trade their former number one overall pick and ace Gerrit Cole (aka the only young pitcher of substance the team has had for the last five years.)

When this happened I lost my shit. This move was a big middle finger to Pirates fans. A team that was short on talent getting rid of their best pitcher.

As if things couldn’t get worse, that starts a chain reaction where a few days later, in yet another cost cutting move, the Pirates trade Andrew McCutchen. Someone who is the most important Pirates player of the post-Barry Bonds* generation. A player whose jersey I own, who is the reason why I watch the team and purchase the MLB Extra innings package, and who deserves a statue in Pittsburgh.

It was at this moment in which I said that I’ve had enough.

I’ve been down this road before and I don’t like where it goes.

In order for a relationship to work both parties have to care. In the case of the Pittsburgh Pirates ownership, they don’t care about their fans.

Right now I have too many choices for my attention and dollars to be spending any of it on something that makes my life worse. A Pirates organization who has treated me like absolute dog crap for 21 out of the last 24 years of my life.

If this were a reality show on Bravo you’d think I was on drugs if I kept taking the Pirates back after the way they’ve treated me.

With this current ownership in place I truly believe that the Pirates will not be competitive for an extended period of time. By competitive I mean actually contend for a World Series (aka the same feeling I had when the team won 98 games.)

I feel like Jim Mora when a reporter asks him about the playoffs when trying to imagine actually expecting a World Series out of the Pirates.

The Pirates winning the World Series under this ownership group seems more unrealistic than flying a Back To The Future II hoverboard to Mars and back.

It pains me that it had to get to this point, but I only want things in my life that are going to be enjoyable and make me happy. Unfortunately the Pittsburgh Pirates ownership does not want that to happen for the fans of the team.

I understand loyalty and for that the city of Pittsburgh has my heart. I will always be a proud yinzer (I have a Steelers tattoo for crying out loud.) I do not, however, believe in being loyal to someone who will not reciprocate in kind. Until there is a new ownership group I am out. I will not be giving the Pirates my attention or dollars.

And for those reason I am rooting for the Chicago Cubs.

Rob Cressy

Rob Cressy

Sports loving free throw specialist and yinzer living in Chicago who is awesome most of the time, has run with the bulls in Spain, and is a graduate of Second City's Improv program.