Less than a year later after acquiring Trent Brown on the cheap — New England got its starting left tackle in 2018 by moving from pick No. 95 to No. 143 in a deal with San Francisco last year — they're looking at facing life after Brown, who will be the highest-paid tackle in free agency this offseason.

Brown has reportedly agreed to a four-year, $66 million deal with $36.75M guaranteed with the Raiders, making him the highest-paid offensive lineman in NFL history. Things weren't always easy for Brown as a member of the Patriots, but he parlayed his one season with the team to a big-time contract. 

So what's next for the Patriots at that spot? The most logical answer would be for Bill Belichick, Dante Scarnecchia and Josh McDaniels to lean on their first first-round pick from last spring.

When Isaiah Wynn was drafted with the No. 23 overall selection last year, many figured he projected as a guard at the NFL level because he stands at 6-foot-3 with 33.5-inch arms.

But not long after Wynn was drafted, Scarnecchia scoffed at the notion that Wynn couldn't play tackle because of his length.


"That [expletive] is way overrated," he told reporters back in May.

The 71-year-old offensive line coach added: "He's played left tackle in the best conference in America. Played it pretty good. We're going to take a look at it, and see how it goes."


Wynn saw snaps at left and right tackle in training camp practices, and he played nine snaps at right tackle in a preseason game against the Eagles before tearing his Achilles. And therein lies the source of some uncertainty if the Patriots want to make Wynn the next in line to protect Tom Brady's blind side. 

Can the team trust a red-shirted rookie with one of the most valuable positions on the field? And can they trust a player whose effectiveness is largely dependent on his agility when that player is a year removed from a torn Achilles?

Unless they want to spend another top-end pick on a tackle in this year's draft — and there are several expected to go in the first round — their options are relatively limited.

If they went that route in the draft, then they could be effectively blocking Wynn from contributing through his first two years as a pro. The guard spots — manned by the well-compensated Shaq Mason and the incredibly durable Joe Thuney — are spoken for, as is Marcus Cannon's gig at right tackle.

Depth on the offensive line is critical, of course, and no one knows that better than the Patriots. So there's value in having the type of super-sub Wynn could be, thanks to his experience at the University of Georgia playing both guard and tackle. But that's something the Patriots typically try to find in players like Cole Croston (who has practiced at guard and tackle), Ted Karras (who plays all three spots on the interior) or LaAdrian Waddle (a free agent who has experience at right and left tackle). Not a first-rounder. 

Will Wynn definitely work out at left tackle? Impossible to say. Just as it was impossible to say last year when Brown — who played primarily right tackle in San Francisco — ended up being the choice a year ago. But the Patriots owe it to themselves to trust their initial assessment and try out Wynn on the edge. 

He's far from a sure thing. But right now — given the cost of keeping Brown, what little is available in free agency and the state of the offensive line as currently constituted — he's looking like their best bet.

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