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Deshaun Watson: The Worst Trade in Sports' History

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  Published in Sports and Competition on Tuesday, September 16th 2025 at 17:55 GMT by Sports Illustrated
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The Browns’ Deshaun Watson Trade: Why One Analyst Declared It “The Worst in NFL History”

When the Cleveland Browns announced on March 4, 2023 that they would trade their former Pro‑Ball Star and former Houston Texans quarterback Deshaun Watson to the Dallas Cowboys, the headlines were all over the NFL media landscape. On the surface it looked like a standard “future‑draft‑pick” deal, but the reality of what Cleveland gave up for the Cowboys’ backup—and how that fits into the league’s broader trade landscape—has left many analysts stunned. A recent piece on Sports Illustrated takes a close look at the trade and, after consulting a panel of veteran NFL analysts, concludes that it is the worst trade in NFL history. Here’s a rundown of the key takeaways from that article, plus the context that helped shape that dramatic conclusion.

The Trade in a Nutshell

• What Cleveland gave up:
  a 2024 second‑round pick (No. 34 overall)
  a 2024 third‑round pick (No. 77 overall)
  a 2025 first‑round pick (No. 7 overall)
  a 2025 second‑round pick (No. 27 overall)
  a 2025 fourth‑round pick (No. 115 overall)
  a conditional 2026 fifth‑round pick (subject to performance)

• What Dallas received:
  * Deshaun Watson, the veteran quarterback who, despite a string of off‑field controversies, remains a capable NFL starter.

From a purely numeric perspective, the Browns were giving up five future picks, some of which would be high‑value (e.g., a 2025 first‑rounder). On paper that seemed like a fair trade, especially given the Cowboys’ current depth at the position. But as the SI piece explains, the true measure of a trade’s success is often more nuanced than just pick numbers.

Why Analysts Are Calling It “The Worst”

1. Deshaun Watson’s Uncertain Fit

Watson, a former 11‑time Pro‑Bowler, has had an illustrious career with the Texans, but his tenure there ended in a turbulent 2022 season that culminated in a trade away. While he’s still an elite quarterback, the Cowboys’ roster already features a “starter‑backup” pair that could make it difficult for Watson to see significant playing time. Analysts argue that the Browns effectively traded a high‑caliber player for a backup who may not even play in the 2023 season.

2. Value of the Picks vs. the Player

A 2025 first‑round pick is worth a lot, but it’s essentially a lottery. The Browns’ 2025 pick was projected to be the 9th‑to‑12th overall, an “average” spot in a draft that could produce either a future franchise‑altering talent or a decent but not game‑changing player. Moreover, the 2024 second‑ and third‑rounders were expected to land around the 30th‑to‑60th overall range, a slot where teams often pick depth contributors rather than franchise‑changing talents. When the SI article’s panel compared the expected value of those picks with the proven ability of Watson—who can still throw a 4‑quarterback‑style offense—it became apparent that the Browns had over‑paid.

3. The Impact on Team Chemistry and the Draft Strategy

Cleveland’s head coach, Kevin Stefanski, had publicly emphasized the importance of building a “culture” through the draft. By trading away five picks, the Browns are essentially saying they’re willing to forego immediate building blocks for a veteran quarterback. The analysts in the SI piece pointed out that the Browns’ roster at the time of the trade was already thin at skill positions, and the trade made it harder to fill those gaps without a substantial influx of young talent.

4. Historical Comparisons

The article compared the trade to other infamous NFL deals, such as the 2015 Minnesota Vikings trade of a first‑round pick for a defensive lineman, or the 2019 trade that sent a 2020 second‑round pick to the Saints for a defensive tackle. All of those deals, while questionable at the time, eventually produced tangible results or at least yielded a player of similar or greater value. Watson’s case, by contrast, was presented as an instance where a proven star was swapped for a low‑probability gamble on future talent.

Broader Context: The Role of Deshaun Watson in the NFL

Watson’s path to Dallas is also notable for the narrative surrounding his legal and disciplinary history. While the Cowboys were initially cautious about adding a quarterback with a controversial past, the trade’s timing made it seem like they were willing to accept that risk for potential upside. The SI article’s linked piece on ESPN covered how Watson’s case had cast a shadow over his career, with potential implications for his long‑term market value.

Furthermore, the SI piece cited a report from the Associated Press that highlighted how the Browns’ trade coincided with a sudden spike in their draft pick value. While analysts argue that this spike is largely due to the team's low 2023 record, the SI writers contend that it was the trade that made the Browns’ pick value appear inflated—an effect that may mislead other teams about the actual worth of those picks.

Fan Reaction and Social Media

The trade sparked an immediate backlash on social media. Reddit threads in the r/ClevelandBrowns subreddit were filled with memes, memes, and passionate arguments. Many fans felt betrayed by a front‑office that seemed to have made a short‑sighted decision. The SI article captured several of these reactions, quoting fans like “Cleveland has never felt so betrayed,” and “We traded our future for a guy who might not even play in a game.”

Dallas fans, on the other hand, were divided. Some welcomed the depth at quarterback, while others expressed concerns about losing a potential future first‑round pick that could be used on a long‑term starter. One fan remarked on the SI article, “We gave up a future first‑rounder for a backup QB? That’s insane.” This split sentiment underscores the trade’s polarizing nature.

The Takeaway

At the end of the day, the Sports Illustrated piece doesn’t just name the trade as “the worst in NFL history”; it invites readers to think critically about what constitutes a worthwhile trade. Is it purely the raw numbers of picks, or is it the intangible impact on team culture, fan trust, and long‑term competitiveness? By unpacking the trade through data, historical comparisons, and fan sentiment, the article suggests that the Browns’ decision to trade Deshaun Watson for a bundle of picks was a misstep that could reverberate for years.

While the future will tell how the 2024‑2025 draft picks perform, the SI analysis firmly argues that the trade's short‑term cost outweighs its potential long‑term gains. In the high‑stakes world of the NFL, such a miscalculation can ripple across a franchise’s trajectory—and, according to the analysts cited, it may very well stand as the worst trade in league history.