A few years ago I was walking around Wrigleyville on a night when the Cubs were slated to make their AppleTV debut on a Friday night. I couldn’t find the game on the screens of any local bar, not even the ones housed in the Cubs office building at the corner of Clark and Waveland. It was an early warning about the ways packaging a game or 20 here, a TV contract or two there, to different streaming services could limit the ability of fans to watch their favorite teams.

Fast forward to the 2025 playoffs. As I noted in my A Cubs Fan’s Guide to the Wild Card Series, one of the best parts of the early rounds is the sheer number of games each day:

The Wild Card round begins tomorrow, with wall-to-wall coverage of Postseason matchups. Every day there are four games is basically baseball’s version of March Madness.

In retrospect, I should have put an asterisk on that statement. Because part of the brilliance of March Madness is its accessibility. Knowing that you can flip the channel from the games on network TV to games on basic cable that almost everyone has figured out some way to watch, at least if they care about watching sports. That was not the case through the early rounds of the playoffs this season and almost all of the complications stem from the sheer number of providers covering the playoffs.

For the Wild Card Series, fans who wanted to watch the MLB Postseason needed access to ABC as well as ESPN and its suite of streaming partners/channels:

Major League Baseball

That’s relatively straightforward, and if you were watching baseball this season you likely already had a way to access ESPN whether through your cable package or via streaming.

And then came the debacle of the Division Series, which is basically a split between TBS and Fox coverage, but with mergers, additional TV channels, streaming deals and pay cable provider deals adding layers of complication to each individual streaming service, well, let’s just say that escalated quickly. The National League is playing on TBS (more there in a second) and the American League is playing on Fox.

Streaming sports on Fox is relatively easy if you have a cable provider, you just log in with that cable provider. If you don’t have a cable provider you can pay $19.99 per month to watch the MLB Postseason on Fox. But if you want to watch on your larger TV, you may be out of luck unless you subscribe to a package that includes FS1 and FS2, because Fox isn’t about to interrupt shows like Murder in a Small Town or Doc for playoff baseball. This conflict was particularly groan-inducing when a rain delay in Detroit pushed the Game 3 elimination game start time to the exact same time as the Yankees v. Blue Jays.

To put this in perspective, as a Cubs fan I have a cable package that basically includes tier two of sports in order to get Marquee Sports Network. That package does include FS1 (yay baseball on my bigger screen!) but it does not include FS2, so the only opportunity for me to watch the Tigers/Mariners game was streaming on my computer or heading to a bar with multiple TVs.

I can hear y’all firing up in the comments already. The games were at the same time. I was going to have to stream one or leave. Point taken, although it would be cool if MLB could get guarantees from the networks its selling their best games to that those games would be visible on easily accessible channels. I recognize this is not merely an MLB problem, but that doesn’t make it less aggravating. I wish I could watch early Stanley Cup Playoff games, NBA and NFL playoff games on the networks as well.

But it got to a whole other level of complicated for the National League teams who are being hosted on TBS. If you have cable, turn your TV to TBS, TNT or TruTV — that’s simple enough. What about streaming, though? Well, I found out just how absurd it was this week trying to help my parents find Game 3 of the Phillies/Dodgers series.

My parents are currently at an AirBnB because my baseball-loving dad is playing in the Huntsman Senior Softball Games. After a long day of softball games they wanted to watch the playoffs, but their AirBnB only has streaming via a Roku. No problem, I know they have access to MLB.TV, Hulu (with an HBO Max addon) and their own cable provider. I am surely up to the task of explaining how to log into an app at their AirBnB that will get them access to this game.

(Narrator voice: she was not up to the task)

We started with MLB.TV where you should be able to log in with a cable provider to authenticate, but the fine print there is more difficult than you’d think:

This works if you have a massive cable provider, but if you rely on a smaller rural network not managed by one of the larger conglomerates? Well, there’s not really a way to log in and authenticate, so your MLB.TV login will only get you the game 90 minutes after it’s over.

That’s fine, HBO Max is supposed to have these TBS games, right? And my parents have access to HBO Max. We get them logged into Hulu at the AirBnB, they find the tile for the game. I can feel my powers as the oldest daughter solving problems growing by the minute, only to be told it wants to charge them $98 right now to be able to immediately stream those games. Apparently there is a difference between accessing HBO Max via their app and having it as an add-on to another app.

45 minutes later, they were all ready to head to a local bar rather than try any additional logins that told them they were blacked out. I found this particularly amusing since they are staying with a lovely Mormon couple who likely has never considered going to a bar.

Is it possible that my parents weren’t reading the streaming fine print correctly? Of course it is. Is it possible there actually is a way for them to authenticate their cable provider that we just missed in 45 minutes of fiddling around with logins and apps and the like? Absolutely.

But it’s also undeniable that a group of people who love baseball so much they are still playing softball at 75 years old couldn’t figure out how to watch the game despite being subscribed to MLB.TV, cable and Hulu/HBO Max.

MLB cares so much about viewership it’s shaved seconds off every at bat to make the game slightly more palatable to the masses. They’ve changed decades old rules to incentivize more action and stolen bases. But they are happy to take their premier product, the Postseason, and make it as difficult (and expensive!) as possible for their most loyal fans to access the most exciting games.

The most disheartening part of this particular journey for me is how clearly I saw this day coming three years ago when the Cubs were on AppleTV for the first time. As I said then:

If you stream it, they won’t come. Unless you do a better job explaining where games are to fans.