Why Some Logos Hit Differently and Why Some Just Don’t Stick?

Alright, welcome to something new I’m kicking off here: Design, Sports & Technology. Think of this as the space where I get to nerd out about the stuff I’m always rambling about anyway: sports logos, jerseys, branding, screens, culture, the whole package. And honestly, there’s no better place to start than with one of my favorite debates: why MLB logos seem to age like fine wine while some NBA and NFL logos… well, don’t.

And yeah, you already know where this starts: the New York Yankees.

Let’s be real, every kid in this country knows the Yankees. They might not know who the shortstop is, they definitely don’t know they haven’t won a World Series since 2009, but they know that logo. It’s just always there. Even people who don’t follow baseball rock Yankees caps like they’re a fashion brand, not a team.

Compare that with, say, the Minnesota Timberwolves. Solid team. Great star in Anthony Edwards. But are kids out there wearing a Wolves logo just because it looks cool? I’d bet the answer is no. Outside Minnesota, I don’t think most kids could even describe the logo. And it’s not just the Wolves, it’s most of the NBA, honestly.

So what’s going on here? Why is baseball, a sport we all claim is “getting older,” the one with the logos that feel permanently plugged into the culture?

Let’s break it down the way we’d talk about this on the couch during a game.

The iconic MLB logos, the Yankees, Dodgers, Tigers, Cardinals, were designed for a totally different world. There was no brand refresh, no social media avatars, no digital anything. These marks had to look clean on a newspaper, a ticket stub, or a wool jersey that probably felt like sandpaper. That simplicity, clean letters, classic shapes, nothing extra, is exactly why they still work today. They weren’t trying to be trendy. They weren’t designed for a hype cycle. They were designed to last because no one had the tools to make them complicated. Ironically, that’s what makes them timeless. Meanwhile, the NBA really went wild in the ‘90s and 2000s. Flames, claws, gradients, metallic stuff, every team wanted to look like an energy drink. Some of those logos are fun, sure, but iconic? Harder case to make. That era defined a moment, but it didn’t define forever.

Everyone always assumes the Yankees logo is everywhere because the Yankees won a lot. But let’s be real, winning alone doesn’t make a brand immortal. The Spurs won five titles and still feel like a regional team. The Heat won with LeBron and still aren’t a global brand on their own. Now take the Chicago Bulls. For us ‘80s kids, that logo practically raised us. Michael Jordan was bigger than sports, and the Bulls logo rode shotgun to all of it. But here’s the wild part: As huge as Jordan was, the Bulls today aren’t treated like this massive forever brand the way the Lakers or Celtics are. Jordan overshadowed the logo so much that once he left, the brand froze in time. It’s like the Bulls are iconic for a moment, not across every generation. The Yankees are iconic no matter when you were born.

This is where design and tech collide. Logos aren’t built for hats or physical merch anymore, at least not first. They’re built for thumbnails, TV lower thirds, TikTok edits, social feeds. Everything is tiny, digital, and constantly moving. If your logo doesn’t pop in a two-centimeter square on someone’s phone, you’re already losing. Kids don’t discover logos through ESPN anymore. They see them in highlight clips, gaming streams, influencers’ fits, or random TikTok dances. And that’s the Yankees’ secret weapon: their logo is already a fashion logo. People don’t wear a Yankees cap because Aaron Judge hit 50 home runs. They wear it because that cap fits every style, every era, every trend cycle. You can put that NY on a runway, a rap video, or a Little League field and it works everywhere. There’s no NBA team with that kind of universal drip. Not even the Lakers.

The NBA’s challenge is actually its biggest strength: the player is the brand. In the NBA, people follow stars, not teams. Kids are wearing Curry jerseys, not Warriors logos. They’re wearing Giannis gear, not Bucks gear. Wemby is going to sell more than the Spurs logo ever will. In a league built on personalities, the team logo becomes background noise. And with players constantly switching teams, any long-term identity gets disrupted. The NBA is powered by constant reinvention, new stars, new styles, new storylines. Great for entertainment. Terrible for logo longevity.

Honestly, baseball logos hit that sweet spot. Simple enough to be timeless. Old enough to feel classic. Stylish enough to survive outside the sport. MLB logos are the vinyl records of sports branding, they never stop being cool, even if the medium around them changes. The Yankees don’t need to win another title for people to keep wearing that cap. The logo has already surpassed the titles. It’s part of the culture at this point.

This new column, Design, Sports & Technology, is where I want to keep digging into this stuff: where a logo becomes a lifestyle, where nostalgia meets design theory, and where a team’s identity becomes bigger than the team itself. If the Yankees logo proves anything, it’s that good design outlasts everything, including the dynasty behind it.