If you were anywhere near the internet in April 2021, you probably remember the chaos. One minute, Barstool Sports founder Dave Portnoy is arguing about pizza or stocks, and the next, a very private video is suddenly very public. At the center of that firestorm was Sydney Raines, an Instagram model and nanny from Atlanta who found herself in the middle of a digital whirlwind overnight.
Honestly, the way most "scandals" go, you'd expect a tearful apology or a PR-scrubbed statement. That didn't happen here. Instead, what we got was a masterclass in owning the narrative—even when the narrative involves a leather leash and a massive dip in a multi-billion dollar stock price.
The Viral Moment That Shook Penn National Gaming
It started as a rumor on Reddit and Twitter. Then the clips hit. The footage showed Portnoy and Raines in an intimate setting—one that included some kinky elements, specifically a leash and collar. It was raw, it was private, and it definitely wasn't meant for us to see.
The timing was brutal for the business side of things. Penn National Gaming, which owns a significant chunk of Barstool, saw its stock price stumble as the video made its rounds. Portnoy, never one to mince words, hopped on Twitter to address the "buy the dip" opportunity. He basically told investors they were being ridiculous.
"A stock is down because somebody has consensual sex? Are you f---ing kidding me?"
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He wasn't wrong, but the market is a finicky beast. People were freaking out, but Dave was just... Dave. He acknowledged it was his "third one" and moved on.
Who Is Sydney Raines?
Before the leak, Sydney Raines was living a relatively quiet life in Atlanta. She was 22 at the time and working as a nanny—a job she’d held since she was a teenager. She wasn't some Hollywood A-lister; she was a "country girl" with a growing Instagram following.
When the video surfaced, she was literally at her nanny job. Imagine getting a text from a friend asking if you're "okay" while you're looking after kids, only to find out your private life is the #1 trending topic on the planet. Most people would go into hiding. Sydney did the opposite.
The Response That Broke the Scandal Cycle
The most fascinating part of the Dave Portnoy and Sydney Raines saga isn't the video itself. It’s how she handled it. Usually, the woman in these situations gets vilified or plays the victim. Raines refused both roles.
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She posted a statement on Instagram that was shockingly blunt. No apologies. No "I'm so sorry for my mistakes." She confirmed it was her, confirmed it was consensual, and called the leak itself the true mistake.
- Consensual: She was very clear that nothing happened without her okay.
- Dated: The video was actually from July 2020, filmed at Portnoy’s Nantucket home.
- Friendly: She and Portnoy remained on good terms with "no animosity."
She even joked with fans in the comments. When someone mentioned her neck must be sore, she asked for a good chiropractor recommendation. That kind of "zero-fucks-given" attitude is rare, and it actually helped kill the scandal faster than a PR firm ever could.
The Business Insider Fallout
We can't talk about Sydney Raines without mentioning the broader context of the allegations against Portnoy. A few months after the Raines video, Business Insider published a heavy-hitting piece featuring other women who described violent sexual encounters with Portnoy.
It’s important to distinguish the two. While those women, like the one pseudonymously named "Madison," described feeling "like a human sex doll" and being in pain, Raines was adamant that her experience was entirely different. She defended her encounter as kinky but consensual. This nuance is where things get complicated. Critics argue Portnoy has a pattern; supporters point to Raines as proof that his "rough" style is just a preference shared by consenting adults.
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Why We Are Still Talking About This
The internet doesn't forget. Even years later, people search for the Dave Portnoy and Sydney Raines connection because it was a turning point for how digital creators handle privacy violations.
- The "Kim K" Comparison: People tried to say Sydney leaked it for fame. She denied this vehemently, even turning down deals to strip or do OnlyFans at the time. She wanted her "conscience" clear.
- The Legal Reality: Portnoy reminded everyone that distributing the video was a federal crime. In the age of "revenge porn" laws, the focus shifted slightly from "look at what they did" to "who leaked this?"
- The Barstool Brand: If anything, the incident reinforced the "El Pres" persona. It didn't "cancel" him; it just added another chapter to the book of Barstool.
Lessons from the Leak
If you ever find yourself in a situation where your private life becomes public, the Raines approach is actually a pretty solid blueprint.
- Don't apologize for legal, consensual acts. Shame is a choice.
- Address it quickly. Letting rumors fester just makes them grow.
- Control the platform. She used her own Instagram to speak directly to her followers.
Sydney Raines eventually moved on. She didn't become a career reality star or a professional victim. She stayed "Syd." Portnoy, meanwhile, continued to build his empire, eventually buying Barstool back for a dollar and then selling it again (it's a long story).
If you're looking for deeper insights into how to protect your digital privacy or how to navigate the messy world of online reputation management, the first step is auditing your own digital footprint. Make sure your "private" content is actually secure—because as we saw here, once the bell is rung, you can't un-ring it. You can only decide how you're going to stand while everyone is looking.
To stay ahead of how these digital scandals impact the market and personal brands, you should:
- Check your privacy settings across all cloud storage accounts to ensure "sharing" is disabled for private folders.
- Enable Two-Factor Authentication (2FA) on all social media and messaging apps to prevent unauthorized leaks.
- Understand local "Revenge Porn" laws so you know your rights if private content is ever distributed without your consent.