A viral X thread has reignited a long-standing debate over Donald Trump’s reputation in American business and sports, a reputation forged decades before he entered politics. The discussion erupted after one user shared his personal reasons for opposing the former president, pointing to financial controversies and failed NFL ownership bids from the 1990s and early 2000s.
I’ll help you understand. Trump was a joke in the 90’s and early 2000’s. A bafoon and the butt of jokes everywhere. The NFL agreed and they kept them out of the league as an owner twice b/c of his bad business dealings the first time (he sued and got a $1) then the 2nd time he…
— Silver Back (@stevieblackjd44) October 30, 2025
Why Did the NFL Keep Donald Trump Out of the League?
Donald Trump Tears Into NFL’s New Kickoff Rule
Donald Trump Tears Into NFL’s New Kickoff Rule (Image Via Instagram/@christinalorey)
The user’s central claim revolves around Trump’s contentious relationship with the NFL. The businessman’s failed attempt to purchase a franchise reportedly stemmed from his refusal to disclose his financial records, which was a major red flag for league officials. This situation followed his earlier involvement with the USFL, where he advocated for a head-to-head challenge against the NFL that ultimately ended in disaster. Although the USFL technically “won” its lawsuit against the NFL, the league received only one dollar in damages.
This wasn’t an isolated incident. Financial records from the 1990s and early 2000s paint a similar picture of turmoil, as companies controlled by Trump filed for multiple bankruptcies affecting his hotels, casinos, and real estate projects. The fan who started the thread cited this history as a pattern of mistrust, describing “1st hand accounts from people I know and have worked with, of him absolutely [messing] them over in real estate or construction deals by not paying and/or filing for bankruptcy to avoid debt service.”
What Are Fans Saying About This History?
Feb 9, 2025; New Orleans, LA, USA; President Donald Trump on the sideline before Super Bowl LIX between the Philadelphia Eagles and the Kansas City Chiefs at Caesars Superdome. Mandatory Credit: Geoff Burke-Imagn Images
Feb 9, 2025; New Orleans, LA, USA; President Donald Trump on the sideline before Super Bowl LIX between the Philadelphia Eagles and the Kansas City Chiefs at Caesars Superdome. Mandatory Credit: Geoff Burke-Imagn Images
The thread quickly gained traction as others weighed in, either defending Trump or expanding on the criticism.
One user wrote, “He’s not a corrupt politician he’s just a corrupt person. I’ll leave it right there.”
The conversation also touched on broader frustrations with Washington, with another user remarking, “Everyone in that cesspool of a city is corrupt.”
However, some participants pushed back against the idea that these were just opinions.
One user emphasized that the allegations were based on public information, stating, “The NFL info is factual and easy to look up, the bankruptcies are on record. The liens filed against him by people he refused to pay are on record. What hearsay and assumptions?”
Ultimately, the heated exchange reflects how Trump’s pre-political past continues to fuel division. While some supporters see his wealth as definitive proof of his success, critics, like the viral poster, argue it’s a mirage built on debt and litigation. For them, the old NFL dispute and recurring bankruptcies have become symbolic talking points, insisting their distrust is about his business record, not just his politics.