So you’re staring at your phone at 9 AM, coffee in hand, trying to figure out why “teddy bear” belongs in a group with “big stick” and “Bull Moose.” Welcome to NYT Connections puzzle #987 from February 22nd, where the categories are delightfully weird and your brain needs a second wind before you’ve even opened your email.
The New York Times really outdid themselves this week. While some puzzles feel straightforward, today’s offerings had layers. Real layers. The kind that make you question whether you’re solving a puzzle or taking a history exam.
Misfits and Outcasts: The Easiest Win
Let’s start with the yellow group because, honestly, you probably nailed this one. The category was straightforward: one who doesn’t fit in. The answers were black sheep, misfit, outcast, and reject.
This is the stuff Connections does well. These four words are basically synonyms, and once you spot one, the others fall into place like dominoes. It’s the appetizer before things get weird. The warm-up lap.
You probably got this one without breaking a sweat, which is exactly how the puzzle designers want you to feel before everything falls apart two categories later.
Silver Linings and Distinguished Looks
The green group took a different approach entirely. We’re talking about descriptors for graying hair, and the Times went surprisingly poetic with it. Distinguished, flecked, salt-and-pepper, and silver.
Here’s where it gets interesting. These words work on multiple levels. “Salt-and-pepper” is the obvious hair reference, but “distinguished” and “silver” could mean a dozen other things. That’s the trap. Your brain wants to connect them to money, to age, to wisdom, to everything except hair.
“Flecked” is the real trick here. Most people don’t immediately think “gray hair” when they see that word. But once you realize all four describe graying hair specifically, it clicks. The puzzle is playing with your assumptions about what these words typically mean.
Comic Strips Nobody’s Read in Years
Here’s where we get nostalgic. The blue group is classic comic strips: Blondie, Bloom County, Peanuts, and The Far Side.
It’s funny how these exist in this weird zone for younger players. They’re iconic, referenced constantly, but most people under 30 have only encountered them through memes or their parents’ newspaper reading habits. The comics themselves? That’s ancient history.
Bloom County is the wildcard here. It’s got the most cult following of the bunch, and some people might not immediately group it with Peanuts and The Far Side. But once you’re in this section of the puzzle, the connections feel solid.
Theodore Roosevelt, The Gift That Keeps Giving
And then we hit the purple section. The hardest group. The one that makes you think the puzzle makers are just having fun at your expense.
Associated with Theodore Roosevelt, we’ve got big stick, Bull Moose, Rough Riders, and teddy bear.
Let’s break this down because it’s genuinely clever. “Big stick” comes from his foreign policy doctrine. “Bull Moose” was his progressive party. “Rough Riders” were his regiment. And “teddy bear”… well, that’s named after him, though the actual origin story is way more complicated than most people think.
The reason this category is brutal isn’t because these words are obscure. It’s because they could each fit into completely different categories in your mind. “Teddy bear” sounds like it should be in a children’s toys group. “Rough Riders” could be a sports team. “Bull Moose” could be… well, an actual animal descriptor.
But the puzzle is asking you to find the connection that ties them all together. That requires knowing your Teddy Roosevelt trivia, which is exactly the kind of niche knowledge these puzzles love to test.
Why We Keep Coming Back
The New York Times has built something genuinely addictive with Connections. Unlike Wordle, which is purely vocabulary-based, Connections requires you to think laterally. You need to understand wordplay, cultural references, and sometimes just obscure connections that make you go “Oh, I get it now.”
The Technology behind these daily puzzles isn’t complicated, but the design is brilliant. Each category has an intended difficulty level, and the purple group is specifically designed to frustrate you just enough that solving it feels like a genuine accomplishment.
The Times even added a Connections Bot so players can track their performance over time. They’re not just making puzzles anymore. They’re building a platform where people can obsess over their stats and compare win streaks. It’s gamification, but it works because the core puzzle is legitimately good.
The Weird Connection Between Everything
What makes Connections fascinating is how often the connections feel arbitrary until they don’t. You’re sitting there thinking “why are these four random things grouped together?” and then someone else explains it and suddenly it seems obvious.
That’s the puzzle’s superpower. It’s not testing your knowledge so much as it’s testing your ability to think like the puzzle makers. You need to understand what they consider a valid connection, what they think is clever, what obscure reference they’re going to pull from history or pop culture.
Some days that means knowing about dead presidents and old comic strips. Other days it might mean understanding internet slang or spotting wordplay. The puzzle rotates through topics constantly, which keeps it fresh.
Is it perfectly fair? Not always. Is it sometimes frustrating? Absolutely. But is it the reason thousands of people solve it every single day? Yeah, that too.
