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Bill Belichick potentially secured his quarterback of the future in the first round of the 2021 NFL draft. Three years ago, he thought he did the same thing at another key position. However, the New England Patriots still don’t know for sure whether Isaiah Wynn can hold down the left tackle position for good.

Luckily for the talented offensive lineman, he can look forward to a significant raise in 2022. But will the Patriots’ $10 million gamble on Wynn’s future pay off? Because if history repeats itself, New England could be stuck in an unenviable situation.

Isaiah Wynn hasn’t exactly lived up to his first-round pedigree

The Patriots possessed two first-round picks in the 2018 draft. Although Belichick could have taken Lamar Jackson 23rd overall, he passed on the chance to build around the dynamic quarterback. Instead, he took Wynn, who earned first-team All-SEC honors in his final year at Georgia.

A talented pass protector with solid athleticism and movement skills, the 6-foot-2, 310-pounder entered the NFL with some question marks about his positional fit. The Patriots thrust him into the mix at tackle, but Wynn’s rookie year ended before it really began, as he suffered a torn Achilles in New England’s second preseason game.

Wynn entered the 2019 season as the team’s starting left tackle. However, a nagging case of turf toe limited him to only eight games. His 2020 campaign came to an end after just 10 starts because of a knee injury.

When healthy, Wynn has shown the ability to perform at a high level. But the fact remains that durability issues have kept the former first-round pick off the field far too often.

The Patriots have officially taken a $10 million gamble on their left tackle’s future

The Patriots have spent the offseason investing heavily on both sides of the ball. Belichick’s expensive free-agent shopping spree filled many of the team’s holes. However, heading into Monday, the future of the left tackle position had yet to be fully addressed.

With Wynn entering the final year of his rookie contract, New England needed to make a decision about extending his stay. Despite his checkered injury history, the Patriots officially took an expensive gamble on his future.

The NFL’s Network’s Ian Rapoport reported via Twitter that the Patriots picked up Wynn’s fifth-year option. That locks the talented tackle into a fully guaranteed salary of $10.413 million for 2022. The 25-year-old blindside protector will make roughly a third of that figure ($3.64 million) this season.

Considering how much time he’s missed since entering the league in 2018, it’s definitely risky to guarantee that amount of money. Will Wynn suddenly stay healthy, play all 16 games, and prove he deserves an extension? Or will history repeat itself? It’s a calculated gamble by Belichick, but one that has big-time upside if all goes well.

New England’s offensive line boasts top-five potential if Wynn stays healthy

Focusing just on 2021, it’s hard not to get excited about the potential of New England’s offensive line. On paper, the unit looks like one of the best in the league. Then again, as Patriots fans have witnessed over the years, an injury or two can drastically alter a protection scheme.

At tackle, Wynn bookends a familiar face who recently made his way back to Foxborough: Trent Brown. A massive man capable of doing serious damage as a run blocker, he should form a devastating duo alongside right guard Shaq Mason. Brown will become a free agent next spring, so he has plenty of motivation to play at a high level again.

Although the Patriots lost Joe Thuney in free agency, they shouldn’t experience much of a drop-off. In fact, Michael Onwenu could develop into an even better player than New England’s longtime left guard. His sheer size and strength allow him to dominate defenders, and he has the upside to become a perennial Pro Bowler.

Onwenu also benefits from playing alongside a vastly underrated player in David Andrews. The veteran center doesn’t have elite physical traits, but his leadership, toughness, and intelligence make him very effective. With Andrews under contract through 2024, the Patriots have the pivot spot taken care of.

If Isaiah Wynn can put his injury issues in the past, expect this unit to control the line of scrimmage on a weekly basis. And that can only lead to good things for Cam Newton or Mac Jones.

All contract data courtesy of Spotrac.

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Sportscasting NFL Writer

Stephen Sheehan

Stephen Sheehan began his sportswriting career as a high school student covering sports for the South Florida Sun-Sentinel through a student outreach program. He wrote for Bleacher Report and Fan Rag Sports and worked full-time for Sportscasting in 2020 and 2021. Stephen specializes in covering the NFL, particularly the New England Patriots.

Stephen is inspired by the stories sports can tell, from money to tragedies to breaking news; there are so many different ways to cover the industry. He monitors Twitter and various websites every day to find stories to tell in unique ways.

Stephen was a 2008 Culpepper Journalism Foundation Fellowship winner, received a bachelor’s degree in journalism in 2013 and a master’s in sports management in 2015 from the University of Florida, and is an active rugby player and former rugby and football coach.