The Trade That Keeps Haunting Cleveland: Carson Wentz and the Pick That Wouldn't Die

On April 20, 2016, the Cleveland Browns held the second overall pick in the NFL Draft and a franchise-defining decision. They traded it away.

What followed wasn't just one bad trade. It was a chain reaction — eleven trades across eleven teams, including the deals that first put those picks in Philadelphia's hands — that turned a single draft pick into a ghost story Cleveland still can't escape. Philadelphia used the pick on Carson Wentz. One of the picks Cleveland received in return later became the selection Houston used on Deshaun Watson. Then, six years later, the Browns paid three first-round picks and $230 million to acquire Watson anyway.

This is the story of a trade that refused to end.

The Bet

The Browns' new front office didn't look like any regime before it. Sashi Brown, a former salary-cap lawyer, was running football operations. His chief strategist was Paul DePodesta — the Billy Beane disciple from Moneyball, hired from the New York Mets to bring analytics to the NFL.

Their judgment on Carson Wentz, the North Dakota State quarterback the Eagles coveted: he wasn't worth it. DePodesta told ESPN's Tony Grossi the team didn't believe Wentz would become a "top 20 quarterback" in the NFL. "In a given year, there may be two or three NFL-ready quarterbacks at the college level," DePodesta said. "In another year, there literally may be zero."¹

So the Browns traded down. The Eagles — who had signed Sam Bradford to a two-year, $35 million contract about seven weeks earlier²² — sent the No. 8 pick, a third-rounder, a fourth-rounder, a 2017 first-rounder, and a 2018 second-rounder to Cleveland for the right to draft Wentz at No. 2, with a 2017 fourth-rounder going back to Philadelphia.²⁴⁹

Head coach Hue Jackson, hired that January, made a promise at the press conference the next day: "We will get this right."²

The Browns had started 24 quarterbacks since 1999.²¹ They had just passed on the chance to end the carousel.

The Immediate Aftermath

Wentz started Week 1 for Philadelphia. His opponent: the Cleveland Browns. He won.⁶

By December 2017, Wentz looked like the best quarterback in football. He had the Eagles at 11-2, had thrown 33 touchdown passes, and was the MVP frontrunner. Then, in Week 14 against the Rams, his left knee buckled. Torn ACL. Season over.¹²

What happened next is the cruelest part of this story — for Wentz, not Cleveland. Nick Foles, the backup, caught fire. He carved up the Vikings in the NFC Championship and outdueled Tom Brady in Super Bowl LII, 41-33, delivering Philadelphia its first Super Bowl title. Foles was named Super Bowl MVP.¹³ Wentz watched from the sideline in a knee brace, a champion who hadn't played a snap in the postseason.

He never played at that level again. In 2021, the Eagles traded him to Indianapolis. A year later, Indianapolis shipped him to Washington. Then came the journeyman years: the Rams, the Chiefs, the Vikings — a backup holding a clipboard, watching other men play the position he'd once owned.¹⁴

In February 2025, nearly a decade after the trade, Wentz was asked which quarterback he'd switch places with for a single game. After a pause, he answered: "I would love to trade places with Nick Foles and win that Super Bowl back in the day."³

What Cleveland Got

The Browns turned their Wentz haul into eleven players. Here is the honest accounting.⁷

The No. 8 pick never even made it to Cleveland's draft card. On draft night 2016, the Browns flipped it to Tennessee, who took offensive tackle Jack Conklin. Conklin became an All-Pro — for the Titans.¹⁶ The Browns got Corey Coleman at No. 15 with the return, a receiver whose Cleveland career was derailed by two broken hands in two seasons. He was traded to Buffalo within two years — and tore his ACL with the Giants in 2019, after he'd left Cleveland.¹⁵

The third-rounder (No. 77) went to Carolina, who drafted cornerback Daryl Worley. The fourth-rounder (No. 100) went to Oakland, who drafted Connor Cook — a quarterback, ironically, who became the first in the Super Bowl era to make his starting debut in a playoff game.¹⁷

Then came the 2017 first-rounder. The Browns held the No. 12 pick — a direct descendant of the Wentz trade — and a quarterback class featuring Deshaun Watson, the Clemson star who'd just beaten Alabama for the national title. The Browns traded the pick to Houston. The Texans drafted Watson.⁸

For the second consecutive year, Cleveland had traded a pick that another team used on its franchise quarterback.

The details sting. Hue Jackson had spent the pre-draft process building a relationship with Watson — workouts, meetings, phone calls. On draft day, CBS reported that Jackson had texted Watson that morning: "Be ready."⁵ Jackson denied sending it on draft day, but Watson confirmed the text existed. "Me and Hue during the draft process kind of communicated," Watson said. "They were a team that was big on me."⁵

They were big on him, and they traded the pick anyway. The Browns took Jabrill Peppers at No. 25 instead.²⁶ They started DeShone Kizer that fall. They went 0-16.²⁵

One piece of the Wentz haul did hit. The 2018 picks — Houston's first-rounder, acquired in the Watson trade-down — became the No. 4 overall pick, which the Browns spent on Ohio State cornerback Denzel Ward. The other 2018 asset, Philadelphia's second-rounder at No. 64, was flipped to Indianapolis on draft night: the Colts drafted Tyquan Lewis, while Cleveland took Chad Thomas at No. 67¹⁰ and sent the extra sixth-rounder (No. 178) to New England, who drafted Christian Sam.¹¹ Ward made the Pro Bowl as a rookie¹⁹ and became a cornerstone of Cleveland's secondary. In a 2020 win over Philadelphia, it was Ward who laid the hit on Wentz that led to a pick-six.¹⁸ The ghost, tackling its own ghost.

The final tally of the eleven players: Coleman, Shon Coleman, Cody Kessler, Derrick Kindred, Spencer Drango, Ricardo Louis, Jordan Payton, Peppers, Kizer, Ward, Chad Thomas. One star. A graveyard otherwise.

The Browns went 1-31 across the 2016 and 2017 seasons.⁷

The Punchline

In March 2022, the Cleveland Browns traded three first-round picks to Houston for Deshaun Watson and signed him to a five-year, $230 million fully guaranteed contract — the largest guarantee in NFL history at the time.²⁰²³

Read that again. The Browns passed on Watson in 2017 using a pick they'd acquired by passing on Wentz in 2016.⁸²⁶ Five years later, they paid three first-rounders and a quarter-billion dollars to acquire the same player they'd once been positioned to draft with the No. 12 pick already in hand.

By then Watson was damaged goods in every sense that mattered — more than two dozen women had accused him of sexual misconduct, he served an 11-game suspension in 2022, and his Cleveland career was soon defined by injuries and poor play rather than the stardom Houston had enjoyed.²⁰ The Browns had come full circle: from declining to draft Watson, to mortgaging the franchise to get him.

Who Won?

The Eagles won a Super Bowl, though the quarterback they traded for watched it from the sideline. The Browns got Denzel Ward and a decade of punchlines. Wentz got a ring he didn't earn on the field and a career that became a cautionary tale about how fragile greatness is.

Sashi Brown said in 2017 he'd make the trade again. "We do like the trade," he insisted. "I think this is a trade that probably will work out for both teams."⁴

A decade later, you can trace every branch of this tree — eleven trades, eleven teams, three years²⁶ — and the only thing it proves is that in the NFL, no trade ever really ends. The picks keep moving. The quarterbacks keep haunting. And somewhere in Cleveland, there's a file with Carson Wentz's name on it, stamped with the coldest evaluation in franchise history: not a top-20 quarterback.

Sources

Explore the trade tree behind this story:

Carson Wentz (2016) trade tree

About this article: it was drafted with AI assistance from the Football Trade Trees database and public reporting, then reviewed by a human editor. Spot an error? Email [email protected].