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NFL's riskiest free agents in 2020: Jameis Winston tops the list

Every free agent presents a certain level of risk.

When the New York Jets tractor-beamed C.J. Mosley away from Baltimore, expectations in New York were clear: The $51 million guaranteed handed to the Pro Bowl linebacker all but ensured an improved Gang Green defense in 2019. Nobody expected Mosley to start just two measly games due to a nagging groin injury that ultimately deep-sixed his season.

Long-suffering fans of the Jets were equally certain that star runner Le'Veon Bell, gifted $35 million in guarantees, would flip the switch on an offense long asleep at the wheel. Instead, one of the game's sauciest talents flatlined for a career-worst 3.2 yards per carry behind an inept collection of overwhelmed blockers.

The players listed below are phenomenal athletes with the inherent goods to thrive. I also see at least one red flag with each of these players -- in some cases, a flock of crimson flags whipping in the wind.

Let's dig in:

Jameis Winston, quarterback: Winston will find work because of his upside: He's months removed from lashing defenses for a league-leading 5,109 yards through the air. Only Tom Brady, Drew Brees, Ben Roethlisberger and Peyton Manning have thrown for more yards in a season, but none of them can match BAD JAMEIS. His NFL-worst 30 interceptions buried Tampa week after week, and the season was -- poetically -- wrapped with Winston unfurling a game-ending pick-six in a Week 17 overtime loss to Atlanta.

"It smells as bad as it could possibly smell and it'll smell that way for a long time," Bucs coach Bruce Arians said of his swashbuckling -- and often drowning -- pirate of signal-caller following that season-capping blunder.

With a record-setting seven pick-sixes in 2019, Winston appears to be done in Tampa -- with the Bucs reportedly hot to trot for Brady -- and realistically out of rope as a starting NFL quarterback. No franchise can sell Winston as a QB1 due to his perilous ball security. The risk is reduced in a backup role, but that scenario screams for some under-fire coach turning to Jameis in, say, Week 7 -- and suffering the consequences.

He's an enigmatic talent who can light up the enemy, but no starting passer came imbued with more risk to his game than Winston. What would change in a brand new zip code away from one of the finest quarterback tutors around in Arians?

Leonard Williams, defensive lineman: Not so long ago, Williams beamed as a thundering draft-day home run for the Jets. Highly disruptive over his first four campaigns, Williams earned glowing grades Pro Football Focus, but lacked the sack totals New York was hoping for.

Traded to the Giants last season, Williams reportedly seeks at least $15 million annually. The sides "are not close" on a new deal, per NFL Network Insider Ian Rapoport, which isn't a stunner considering New York GM Dave Gettleman's history for letting overpriced veterans walk.

After a season that saw his pressure rate fall off, Williams comes tinged with questions over whether his early-career promise will ever return. While just 26, the behemoth makes more sense as a transition-tagged performer with plenty to prove before the G-Men -- or anyone -- invest a mountain of money in him.

Quarterback Ryan Tannehill and running back Derrick Henry, anywhere outside of Tennessee: We'll know soon enough how the Titans feel about both players, with RapSheet noting Tennessee is "focused" on inking a long-term pact for Tannehill while bringing back Henry at a "big number."

I'm dubious of any other solution.

Tannehill and Henry should stay right where they are in a get-the-band-back-together assault on the AFC South. My Spidey sense tingles at the thought of Tannehill making starts elsewhere, while Henry -- one of the game's most compelling runners -- works best inside a Titans offense determined to truck cowed opponents behind a top-shelf line.

These two make the Titans go -- and the Titans do the same for Tannehill and his hammer-dropping rumbler. Don't get too cute here, Tennessee.

Melvin Gordon, running back: Gordon's future fortunes boil down to finding the right fit. The Chargers have seen enough, refusing to cave in with a long-term deal during Gordon's botched, into-September holdout. Upon his return, the 26-year-old plodded to the tune of 3.8 yards per carry and too often disrupted the flow of Austin Ekeler's sensational backfield magic. The down campaign doesn't take away from Gordon's electric work in 2018, but his next team should prepare for streaky play with plenty of highs and lows. On the latest Around the NFL Podcast, Buffalo was named as an appropriate landing spot. Pairing Gordon with someone like Devin Singletary makes sense. Solo workhorse duties would loom as a concern after what we saw last autumn.

Robby Anderson, wide receiver: Anderson can play. He's an asset down the field, ranking 11th in deep receiving yards since 2016. It's unfair to call him a one-trick pony, but the undrafted Anderson -- lacking a 1,000-yard season -- fits the Kenny Stills speed role. Someone is about to pay dearly for his services ($12 million to $15 million annually, per NFL Network's Tom Pelissero) while looking past Anderson's off-the-field issues and overall up-and-down play. The counterpoint: Anderson toiled for a sketchy Jets attack and might emerge as money in the bank inside a better offense. It's a roll of the dice.

Jimmie Ward, safety: Making his 2019 debut in Week 5, Ward thrived as a reliable, sure-tackling safety for the Niners. Availability has been a career-long issue, though, with broken bones causing Ward to miss time in five of his six seasons. We know where he fits. The Niners have seen him through a rocky journey -- staying in San Francisco on a fair deal makes the most sense.

Jamie Collins, linebacker: I'm weary of any player bolting New England for a bag of riches. Collins deserves the concern, thriving with the Patriots over two separate stints sandwiched around a disastrous two-plus-year run with the Browns. Granted, those Cleveland teams were nuclear-level messes, but fans and people around the team questioned if Collins was putting forth top effort. Bill Belichick worked him back into form, but Collins also struggled down the stretch last season. It's anyone's guess what he'd morph into if the wrong team came calling.

Jason Peters, offensive tackle: Peters will finish his career as one of the finer linemen of his generation. At 38, though, it's fair to wonder if he can piece together a 16-game season. Injuries limited him to seven tilts in 2017 and knocked him out of three starts a year ago. Tackles are all the rage, but anyone eyeing Peters would alleviate risk with a fair, one-year offer while planning for the occasional absence.

Follow Marc Sessler on Twitter @MarcSessler.

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