Dave Portnoy believes Kayla Nicole is planning to ‘diss’ Taylor Swift

Dave Portnoy, founder of Barstool Sports, has openly criticized media personality Kayla Nicole over her recent Halloween costume, claiming it was intended to mock pop icon Taylor Swift and Kansas City Chiefs tight end Travis Kelce.

Speaking on Barstool’s Wake Up Barstool show, Portnoy argued that Nicole’s post was less about celebrating the holiday and more about revisiting her past relationship with Kelce.

Nicole, who dated Kelce from 2017 to 2022, went viral after sharing a video of herself dressed as R&B singer Toni Braxton.

In the post, she lip-synced to Braxton’s 2000 hit “He Wasn’t Man Enough,” a song whose lyrics describe a woman addressing another about a shared romantic partner.

The video quickly gained traction across social media, prompting both praise for Nicole’s creativity and speculation about her intentions.

Portnoy suggested that the performance was aimed at Kelce and Swift, who began dating publicly in 2023 and announced their engagement earlier this year. He said the choice of song and its lyrical message – including lines implying infidelity and emotional conflict – amounted to a subtle public critique. “She went viral doing a Toni Braxton song,” Portnoy said. “The lyrics are essentially, ‘While your man is sleeping with you, he’s thinking of me.’ It’s clear shots at Taylor Swift and Travis.”

Online Reaction and Broader Context

The online response was divided. Some users interpreted Nicole’s costume as a playful homage to an influential musician, while others agreed with Portnoy that it carried personal undertones. The debate gained traction as media outlets picked up the story, linking the timing of the post to Kelce’s highly publicized relationship with Swift.

Portnoy further contended that Nicole’s decision to reference a relationship that ended several years ago reflected poorly on her public image. “If you’re talking four years later about your ex-boyfriend, you already lost,” he remarked during the broadcast. His comments echoed sentiments he has previously expressed about Nicole’s social media activity, which he believes frequently revisits her time with Kelce.

Toni Braxton herself appeared to appreciate Nicole’s costume, commenting positively on the post. Despite that, the conversation surrounding Nicole’s intentions overshadowed the artistic element of her Halloween tribute. For many observers, the episode highlighted how celebrity relationships continue to shape online narratives even after they have ended.

Kelce and Swift’s relationship has remained a focal point of pop culture coverage throughout 2024 and 2025, with both figures maintaining high visibility in their respective fields. Against that backdrop, any public reference to their partnership tends to draw scrutiny and speculation.

Portnoy’s remarks underscore the sensitivity surrounding public figures and their private histories in the social media era. Whether Nicole’s post was meant as a statement or simply a performance, it reignited discussion about fame, rivalry, and the blurred boundaries between personal expression and public perception.