Bear Digest

6 Super Bowl free agents the Chicago Bears should target

Alan Goldsher|
Philadelphia Eagles defensive tackle Milton Williams
Philadelphia Eagles defensive tackle Milton Williams | Tim Heitman-Imagn Images

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Chicago Bears

The Chicago Bears aren’t playing in Super Bowl LIX. And if we’re being honest with ourselves, the Chicago Bears aren’t anywhere near playing in Super Bowl LX.

But the Kansas City Chiefs and the Philadelphia Eagles are very much in Super Bowl LIX, and each of those teams has a handful of quality players who might hit the free agent market after the clock at the Caesars Superdome lands on triple zeroes.

The Bears could use a bit of Super Bowl fairy dust, so here, in alphabetical order, are some potential Chiefs and Eagles FAs who might look snazzy in navy blue and orange

Mekhi Becton: Philadelphia (OG)

K.C.’s Trey Smith is getting all the publicity, but Becton might be a more logical option. He’s just 25-years-old, he’s a massive 6’7”, 364-pounder, and PFF grades him out at 75.2, making him their 21st-best guard.

Depending on who you ask, his market value lands somewhere in between $10 million and $11 million, thus he’d be considerably more affordable than Mr. Smith.

Kenneth Gainwell: Philadelphia (RB)

When Gainwell gets the rock, he does things with it. But when you're behind Saquon Barkley on the depth chart, there won’t be much rock-getting ever, so the 25-year-old will likely sprint away from the City of Brotherly Love ASAP.

If GM Ryan Poles isn’t interested in drafting Ashton Jeanty (he should be, but whatever), Gainwell could be a good partner for D’Andre Swift. Or a good replacement.

Trey Smith: Kansas City (OG)

Smith is considered to be one of the best free agents on the market —not just one of the best O-lineman, but one of the best players—and the bidding for his services could skyrocket beyond Poles’ budget.

The 25-year-old All-Pro would be a great get, but he’d also be a salary cap sucker. Decisions, decisions, decisions.

Josh Sweat: Philadelphia (EDGE)

Sweat will be entering his age-28 season, and as a high-production pass rusher inching towards his peak, he’ll likely be part of a feeding frenzy. But after Montez Sweat’s meh 2024 season, new D-coordinator Dennis Allen would be thrilled to have Sweat bookends.

Justin Watson: Kansas City (WR)

Watson catches touchdowns.

Since 2022, of his 64 receptions, seven went to the Promised Land. He’s not a speedster, but he has nice hands and runs nifty routes, something the Bears could use if they choose to move on from Keenan Allen.

Milton Williams: Philadelphia (DT)

Here’s a fun stat: PFF tells us that Williams’ 2024 pass rush grade was 90.4, the second-best among D-tackles. Spotrac pegs the Louisiana Tech product’s market value at $12 million, but he’s young, athletic, and proven, so that might be a worthwhile investment.

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Alan Goldsher
ALAN GOLDSHER

Alan Goldsher has written about sports for Sports Illustrated, ESPN, Apple, Playboy, NFL.com, and NBA.com, and he’s the creator of the Chicago Sports Stuff Substack. He’s the bestselling author of 15 books, and the founder/CEO of Gold Note Records. Alan lives in Chicago, where he writes, makes music, and consumes and creates way too much Bears content. You can visit him at http://www.AlanGoldsher.com and http://x.com/AlanGoldsher.

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