Keith 'Roaring Kitty' Gill shook up Wall Street again, taking a $245 million stake in Chewy and sending shares on a rollercoaster ride with a single cartoon dog post and a cheeky 'I am not a cat' declaration.

In a move that had investors chasing their tails, Keith Gill, the notorious 'Roaring Kitty' behind the GameStop saga, acquired a 6.6% stake in Chewy, valued at $245 million. The announcement sent Chewy's stock soaring up to 15% in pre-market trading, only to witness a whiplash-inducing crash. Gill's playful social media antics, including a cartoon dog post on X, added fuel to the market's frenzy. His infamous persona and a tongue-in-cheek 'I am not a cat' SEC filing spread chaos across pet stocks, evoking memories of the meme stock madness he once spearheaded.

Upon the public disclosure of Gill's investment, Chewy shares initially saw a vigorous surge, climbing up to 15% in pre-market trading. However, this jubilant ascent was short-lived. No sooner did the market open than the shares began a tumultuous descent, eventually settling down by approximately 4-5%. Clearly, the market's reaction was as fickle as a cat's mood at a dog's birthday party.

The excitement didn't end there. Gill posted an image of a cartoon dog on social media platform X, sending Chewy's stocks into another short-lived frenzy. This whimsical move prompted a brief but significant boost in the stock price.

Gill, who rose to fame during the infamous GameStop meme stock frenzy, seems to have retained his flare for market disruption. The 2021 GameStop rally, largely influenced by Gill's analysis and social media presence, resulted in a nearly 700% gain for the video game retailer, a ride that many investors are unlikely to forget anytime soon. Notably, GameStop’s tumultuous journey also has a tie to Chewy, as the CEO of GameStop, Ryan Cohen, happens to be a founder of Chewy. Thus, the two companies find themselves linked not only by playful pets but by Gill's audacious investment strategies.

Putting aside feline analogies, Gill's investment isn't just about his characteristic whimsy. His $245 million stake, representing roughly 6.6% of Chewy, is no small change. It demonstrates his significant confidence in the company’s value and its potential for future growth. Of course, with Gill being Gill, his SEC filing didn't shy away from humor. It included an amusing section where he declared, 'I am not a cat,' a nod to a viral moment from 2021 when an attorney inadvertently appeared as a cat in a virtual court hearing—a statement both quirky and quintessentially Gill.

Interestingly, Gill’s purchase sent ripples beyond just Chewy. The news impacted related stocks like PetMed Express and Petco, showing how interconnected the pet industry can be and how a major player's move can unsettle the entire sector. Volatility, it appears, isn’t just a human trait but extends to stocks named after humans' best furry friends.

As investors digest the recent chaos, the question looms whether Gill's confidence in Chewy will pave the way for sustained growth or if this will be another chapter in the annals of market volatility. For now, Wall Street watches intently, paws at the ready, to see what Roaring Kitty will do next. One thing’s for sure: there will be tails wagging and maybe a few hairs standing on end.