The Kansas City Chiefs are working to retain numerous key players to make a legit run at a Super Bowl three-peat. After re-signing Chris Jones to a five-year, $158.57 million extension, however, that task became way more difficult.

As it stands, the Chiefs former starting offensive tackle, Donovan Smith, remains a free agent. After eight seasons with the Tampa Bay Buccaneers, Kansas City signed Smith to a one-year, $3 million deal last May.

While Smith missed a slew of games due to a neck injury, ESPN insider Bill Barnwell says that’s not the main reason the veteran remains a free agent.

“Penalties,” Barnwell wrote.

“Smith has 29 over the last four seasons, which ties him for the third-most of any player. No. 1 is former Chiefs teammate and fellow tackle Jawaan Taylor, so that should be proof that penalties alone can’t keep players from winning a Super Bowl. Smith is 30 and missed the final five games of the regular season with a neck injury before returning in the postseason, so there might be some medical concerns around him as well.”

San Francisco 49ers star Nick Bosa actually called Smith and Taylor out ahead of the Super Bowl. Speaking to reporters, Bosa was asked what stood out about their penalties this season.

“They hold a lot,” Bosa answered.

Taylor, who signed a four-year $80 million contract with the Chiefs last March, was penalized 7 times for holding and 9 false starts in 17 games. Taylor garnered 5 more flags than Jets’ Mekhi Bekton and Ravens’ Ronnie Stanley, who tied for second place (12 penalties).

In 2022, Smith was the second most-penalized offensive lineman (12) while in Tampa Bay. During the 2023 NFL season, he garnered 6 total penalties, 5 for holding, and 1 false start in 12 games.

Chicago Bears are Considered the ‘Best Fit’ to Land Donovan Smith

Despite being penalty-prone, Smith is a serviceable tackle with two Super Bowl rings.

Barnwell noted, “As I wrote before the big game, one of Patrick Mahomes‘ superpowers is avoiding sacks when pressured, but Smith posted a pass block win rate just under 91% during his lone season with Kansas City, suggesting he did a sound job of protecting Mahomes during the first 2.5 seconds of plays. That mark ranked 18th among all tackles.”

Barnwell named the Chicago Bears as the “best fit” to sign the 6-foot-6, 338-pound veteran. “As Ryan Poles and company prepare for the Caleb Williams era, the one thing they’re clearly missing is an upgrade at left tackle, where Braxton Jones hasn’t nailed down a tough job over his first two seasons in the league.

“Signing Smith would give the Bears a veteran on Williams’ blindside while moving Jones into a swing role.”

Bleacher Report’s Gary Davenport is on the same page. “That sort of effectiveness should appeal to any number of teams, from contenders to rebuilders. Given what the Chicago Bears are about to invest in Caleb Williams and the expectations that will come with being the first overall pick, an upgrade on his blind side certainly isn’t a bad idea.”

Davenport also floated the Pittsburgh Steelers and Washington Commanders as possible candidates.

Chiefs News: After Trading L’Jarius Sneed, Kansas City Could Re-Sign Donovan Smith

While Smith hinted on X that his tenure in Kansas City might be over earlier this month, things have drastically changed since.

The Chiefs agreed to trade cornerback L’Jarius Sneed to the Tennessee Titans on March 22. Kansas City had $7.6 million in cap space before Sneed was traded. Once the exchange clears, the Chiefs will have another $19.8 million to spend.

Re-signing defensive end Mike Danna is predicted to be Kansas City’s “first call,” however, keeping Smith could also be on the agenda, per ESPN’s Jeremy Fowler.