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Who’s Cashing in as the Single Biggest Winner of the NFL Postseason?

Last Updated: January 13, 2023
Who has the most to gain and the most to lose on football’s biggest stage? Boardroom convenes its GRIDIRON ROUNDTABLE to fire off some NFL Playoff predictions.

Now that you’ve read and probably memorized Boardroom’s FanDuel-powered predictions for the Super Wild Card phase of the NFL postseason that begins Saturday, Jan. 14, it’s time to make like Leo, Ellen Page, and Tom Hardy and go deeper.

In fact, since we’re kicking things off with Super Wild Card weekend, we decided to get super wild as it relates to Super Bowl prognostications and impending free agency/contract extension silly seasons, so we convened our first-ever GRIDIRON ROUNDTABLE — Griffin Adams, Sam Dunn, Chuck McMahon, Anthony Puccio, and Shlomo Sprung — to respond to three essential playoff queries in the race for footballing supremacy:

  1. Which team is the most compelling or overlooked Super Bowl dark horse?
  2. Who is the upcoming free agent or contract extension candidate with the most to gain or lose in the Playoffs?
  3. Who’s your pick to win it all and why, and how much are they winning you on a $100 futures bet?

From ballers to bettors and beyond, let’s toss out our best NFL Playoff predictions.

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Who is the most compelling Super Bowl dark horse?

All odds via FanDuel Sportsbook as of Jan. 13.

ANTHONY PUCCIO: The 49ers (+500). I know they aren’t your typical “dark horse” per se, but all the hype is around the Bills, Chiefs, and Eagles — and for good reason — but San Francisco showed us all season how they were able to overcome the kind of injuries that would have put just about any other team out of commission.

The star power is obviously there with CMC, Deebo, Aiyuk, etc. The defense is one of the best in the NFL, and it apparently doesn’t really matter who’s at QB: Jimmy G went 7-3 and Brock “Mr. Irrelevant” Purdy went 5-0. Don’t discount their culture built on continuity behind a championship-pedigree coach in Kyle Shanahan who’s been on the big stage before.

SHLOMO SPRUNG: Remember the Cincinnati Bengals (+750), the team that made the Super Bowl *checks notes* last season? Cincy finished No. 7 in the league in rush defense during the regular season and has all its top offensive skill players healthy. Joe Burrow showed his mettle in last year’s playoffs outdueling Patrick Mahomes in the AFC title game, and Joe Mixon, Ja’Marr Chase, and Tee Higgins are all ready to prove themselves all over again. I know I wouldn’t want to play #WhoDey right now.

GRIFFIN ADAMS: Woof! Outside the top five contenders, which is where I would normally search for a dark horse, I’m not liking much, if I’m being honest. The Cowboys are right there at sixth in terms of odds, but it certainly would feel icky if I picked them as a “dark horse” Super Bowl contender. And since nothing is jumping off the page after Tier 1, I’m thinking I’ll just go with the most proven commodity of the bunch — Tom Brady and the Tampa Bay Buccaneers (+2800).

Let me start off by saying I get it. They’ve been terrible all season long and the “cliff” talks are actually starting to appear somewhat valid as Brady continues to age. That said, as previously mentioned, every other team has something they are dealing with, and I’d rather put my money on the guy who’s won seven Super Bowls over anyone else. Will I? Probably not, but if it’s TB & TB or the field (outside of the top five)? I’m taking TB & TB.

SAM DUNN: Yeah, what he said. I’m not betting likelihood; I’m betting value. If you’re giving me 28-to-1 odds, I’ll take the team with Tom Brady on it. Not for nothing, the Bucs have already beaten their Wild Card opponent, the Dallas Cowboys, one time this season, and the game’s at home besides.

CHUCK McMAHON: You might find this shocking, but watch out for the Los Angeles Chargers (+2100). Seriously. The Bolts boast quite the dynamic offense — one that could mean major problems for any opposing defense in the playoffs. Not only does QB Justin Herbert anchor a top-10 passing game, but Austin Ekeler may be the most versatile running back in the NFL — we’re talking 13 TDs rushing and five receiving on the season.

If the offense can cook and the defense can keep things together for four quarters, expect some electricity out of LA this postseason.

Which free agent/extension candidate has the most to gain or lose?

SD: Jalen Hurts. He’s eligible for an extension for the first time this offseason, and the extent to which he’s able to carry the Eagles back to the promised land could be the difference between landing a new contract in the Kyler Murray/Russell Wilson neighborhood (five years and $230-$240 million) and earning a record-setting deal by average annual value, guaranteed money, or both.

In any event, he’s a free agent after the 2023 season. But a star-making postseason run will surely force the Eagles’ hand one year early if that wasn’t already 100% the plan.

Click here to read Boardroom’s projections for a potential Jalen Hurts contract extension.

SS: Geno Smith and Daniel Jones already proved themselves by even getting to the playoffs in the first place with the Seahawks and Giants, respectively, so they’re already playing with house money as they enter Super Wild Card weekend. If Geno can knock off the 49ers as double-digit underdogs? Add some more millions to his next contract.

If DJ can somehow bring New York to the divisional round or conference title game? Big Blue will have to come to the table with a bigger offer. But if they come up flat this weekend? Let’s just say there will be some lingering doubts moving forward about the QBs being players who can actually lead a franchise to the promised land.

GA: This one’s easy for me: Lamar Jackson.

I’ll take it a step further and say if it was me in his shoes, I would have already decided to sit out this postseason given all the injury questions.

Look, Action Jackson deserves to get paid, just as any starting QB in the NFL who has won a league MVP should. But Jackson and the team have gone back and forth on extension negotiations for the last couple of seasons, with the two sides unable to reach an agreement before the player’s self-imposed deadline of the 2022 season opener.

Now, they still can come to terms on an extension, but as Boardroom’s Randall Williams wrote in September, this can go a number of ways. If he wanted to stay in Baltimore, however, the franchise has shown its cards when it offered a lower offer than what Jackson wanted ahead of the season. And since the QB didn’t win MVP or light the league on fire with his production this year, will the Ravens really offer more than what they already have?

The only way they would is if LJ can hero-ball his way to a Super Bowl title, which seems unlikely considering he’s not 100%. So, sit out. Preserve your health. Get that money.

CM: Geno Smith. While one could argue that the veteran (and imminent free agent) has already proven himself worthy of a big deal after his standout performance during the regular season that positions him as a compelling Comeback Player of the Year Candidate, can you imagine what a solid Seattle run in the playoffs could do for his stock?

Not only did the 32-year-old set the Seahawks’ single-season franchise passing records — yes, surpassing Russell Wilson immediately following the future Hall of Famer’s relocation to Denver — but he also was named to the Pro Bowl. If Geno can help guide Seattle past the 49ers during Wild Card weekend, expect several QB-hungry teams to put Geno on their radar this offseason.

Click here to read Boardroom’s projections for a potential Geno Smith contract extension.

AP: This is a tough one. The Giants don’t have much to lose overall, but I think Daniel Jones has the most to gain here. He’s already playing with house money since he proved he can be a QB on a winning club, but if he pulls off an upset at Minnesota, more fans will be willing to believe that he can be a big-game QB like Eli Manning proved 15 years ago. These G-Men went 3-5-1 against teams .500 or better — can Jones get the job done against tough teams? I’m sure GM Joe Schoen is curious, too.

Time to predict a Super Bowl winner. Go!

GA: Bird Gang. ‘Nuff said. Billions. (Or technically $100 to win $500).

CM: For the first time in NFL history, a team with a cat nickname will win the Super Bowl.

Cincinnati has scratched and clawed its way to the top of the AFC North and into the playoffs, but I don’t think we’ve seen the best of the Bengals just yet. Between a confident Joe Burrow, a capable Joe Mixon, and a deep receiving corps headlined by Ja’Marr Chase, it’s going to be hard to stop this team from going on a run similar to last year. If I was a betting man, I’d take my $100 futures bet and put it on the Bengals to win the whole damn thing — and win me a sweet $750.

AP: I’ll back the Niners. My $100 bet is winning me $500. Tasty.

SD: It’s finally the Buffalo Bills‘ year.

If there ever was a team of destiny, it’s gotta be the Orchard Park crew, right? They came so incredibly close to the AFC title game only to fall short in an all-time thriller against the Chiefs in last season’s Divisional Round, but one more year of maturity plus the sheer immeasurable aura of inspiration exuded by the incredible Damar Hamlin makes them the ultimate bandwagon team. They were preseason betting favorites to win the big one, and I’ll gladly take them now. A $100 bet wins me $400.

SS: I’m rolling with the San Francisco 49ers. While Brock Purdy was the last pick in the draft, he’s shown that big games don’t faze him. The Niners have the best defense in the league, game-breaking weapons on offense in Christian McCaffrey and Deebo Samuel and haven’t folded in big close games like the Buffalo Bills, haven’t lost momentum down the stretch like the Philadelphia Eagles, or hasn’t lost to a top team like the Kansas City Chiefs did against the Bills and Bengals. I’ll wager $100 to win $500, thanks.

NOTE: Boardroom staff wagers are for entertainment purposes only and are not (necessarily) meant to be taken literally.

Click here to read the Boardroom x FanDuel NFL Playoff predictions for every game of Super Wild Card weekend.

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