Jimmy Haslam Paid $230 Million, Now His Pride Is On The Line, Skip Bayless Explains Why Deshaun Watson Starts Over Shedeur Sanders

The Cleveland Browns entered the 2025 NFL Draft carrying more quarterback intrigue than almost any franchise in the league. They held Deshaun Watson, a quarterback owed $46 million guaranteed for the upcoming season who hadn’t taken a meaningful snap in nearly two years. And they had just selected Shedeur Sanders, a player widely regarded as a first-round talent, in the fifth round of a draft that left the football world stunned.

Now, with training camp on the horizon and a new head coach eager to establish authority, the question at the center of everything in Cleveland is who will start under center? According to veteran sports commentator Skip Bayless, the answer is already being written, and it isn’t the one Sanders’s supporters want to hear.

Reports from Mary Kay Cabot, one of the most respected and deeply sourced Browns beat reporters in the business with nearly four decades covering the franchise, suggest that Watson is being positioned as the frontrunner to reclaim the starting role. Bayless, speaking on his platform, stated publicly that he not only believes those reports but that they trace directly back to ownership, specifically to Browns owner Jimmy Haslam, whose financial and reputational stakes in Watson’s revival are enormous.

The backdrop for Sanders’s arrival was already complicated before a single training camp practice began. He was entering a locker room still psychologically and structurally connected to Watson. He was joining a team that, despite its dysfunction, retained a financial obligation to Watson so large it would define the franchise’s salary-cap reality for the near future. And he was walking into an organization led by an owner who, by multiple accounts, remained deeply invested in seeing his original quarterback gamble pay off.

1. Was Haslam Drafting a Franchise QB or a $230 Million Marketing ‘Sideshow’?

Shedeur Sanders arrived at the 2025 NFL Draft as one of the most scrutinized quarterback prospects in recent memory. Coming off his final season at the University of Colorado under head coach and father Deion Sanders, Shedeur had built a statistical profile and a national following that made him a consensus top-ten discussion in pre-draft circles. His release mechanics, pocket presence, and performance in high-pressure situations were regarded by scouts as legitimate NFL-ready traits. Multiple analysts and pundits projected him as the first overall pick. That projection, as the draft unfolded, could not have been further from reality. Sanders fell through the first round. Then the second. Then the third and fourth rounds passed without his name being called. By the time the Cleveland Browns selected him late in the fifth round, the football media had largely moved from surprise to outrage. Players perceived to be significantly less talented had been taken in premium slots. The fall was interpreted across broadcast desks and social platforms as more of a draft-room decision shaped by factors beyond on-field merit, including the polarizing public profile of his father. Skip Bayless was among the most vocal in characterizing the draft development as something beyond ordinary. He had championed Shedeur Sanders publicly for over a year, stating before Sanders’s final college season that he believed Shedeur should have been the first overall pick. When the fifth round arrived and Cleveland made the selection, Bayless suggested it was a business decision driven by the Browns’ existing quarterback situation, and perhaps by something more cynical. Bayless suggested that Haslam, who controls the franchise with a hands-on ownership style Bayless compared to that of Dallas Cowboys owner Jerry Jones, saw in Sanders not a franchise cornerstone but a marketing asset. A “sideshow,” in Bayless’s characterization, a player with a massive national following that would drive ratings, merchandise interest, and fan engagement at a moment when the Browns desperately needed good news.

2. Skip Bayless Reveals Why Jimmy Haslam’s Pride Will Force Deshaun Watson as Browns’ Starting QB

During his recent appearance on Gridiron, Bayless said, “To me, this confirms my deepest fears for a Shedeur Sanders I love, and I said before his last year at Colorado, he should be the first overall pick, and it was the most shameful draft development I’ve seen in all my time covering National Football League drafts that he fell to the fifth round, at which point I believe Jimmy Haslam, who does run the Browns and is sort of a Jerry Jones wannabe, I believe he was the one who jumped in and said, ‘Take him. We might need him as a sideshow.’ That’s what I believe he said at that moment in the fifth round.” He continued, “They did need him as a sideshow because they knew he had a very strong national following led in part by me, the show, we love him, believe in him. And yet, Jimmy Haslam paid $230 million guaranteed for Deshaun Watson over five years, and he still owes him $46 million for next year. So Jimmy Haslam, his pride is now on the line. And I believe that Jimmy Haslam badly wants Deshaun Watson to be the starting quarterback and a successful starting quarterback next year to prove him ultimately right so he can say, ‘See, I told you he could do this.’” Bayless went on to say, “Deshaun has not played football for about two years. Deshaun has gone to hell and back with his off-the-field issues, as we know. And yet, I believe that Mary Kay Cabot, who has been covering the Cleveland Browns for almost 40 years, is getting this straight from the horse’s mouth. I believe she is so connected, so plugged in …. she is plugged into Jimmy Haslam and his wife, who also has a big say in the franchise, and I believe she’s just — this is — she’s the messenger.”

3. Did Shedeur Sanders’ 2024 Season Stats Already Expose Watson’s Catastrophic Return?

Few financial decisions in recent NFL history have drawn as much scrutiny as Haslam’s commitment to Watson. In March 2022, the Cleveland Browns signed Watson to a fully guaranteed five-year contract worth $230 million, the largest fully guaranteed deal in NFL history at the time. The signing came despite Watson facing more than two dozen civil lawsuits from women accusing him of sexual misconduct during massage sessions. The NFL ultimately suspended Watson for 11 games in 2022 under its personal conduct policy. Watson’s on-field return to the Browns proved disastrous on multiple fronts. He played limited snaps in 2022 following his suspension, struggled with consistency throughout 2023, and then suffered a season-ending shoulder injury in 2024 that required surgery and kept him sidelined for the remainder of the year. By the time the 2025 offseason arrived, Watson had started a combined 24 games for Cleveland across three seasons, a catastrophically low return on a quarter-billion-dollar investment. Yet the financial reality remained unmoved: the Browns still owed Watson $46 million for the 2025 season. Lost in the ownership dynamics and the financial calculus is a football argument that Sanders’s supporters believe is compelling on its own terms. In his seven starts for the Cleveland Browns during the 2024 season, Sanders went 3-4. On the surface, that record reads as unremarkable. In context, it represents something considerably more significant. The Browns’ offensive line that season was regarded by multiple metrics as the worst unit in professional football. Their receiving corps offered Sanders almost no margin for error. He was, by every available measure, operating without the foundational support a young quarterback needs to develop or succeed at the NFL level. Yet within those seven starts, Sanders delivered results that exceeded what his circumstances should have allowed. He defeated Aaron Rodgers and the New York Jets at home. He defeated Joe Burrow and the Cincinnati Bengals at home. He opened his NFL career with a road win in Las Vegas. For a fifth-round rookie operating behind a porous offensive line with limited weapons, those results were not nothing. They were, in the eyes of advocates like Bayless, evidence of precisely the competitive instincts and execution-under-pressure ability that made Sanders a consensus top prospect heading into the draft.

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• Deshaun Watson
• Shedeur Sanders