The 5 Decisions That Will Shape the NFL Offseason
Several dominoes could be about to fall across the league
The NFL offseason is always among the biggest whirlwinds on the sports calendar, but this year five big decisions could shape what the entire league looks like when the dust settles on free agency and the book closes on the 2024 NFL Draft.
The Chicago Bears’ Caleb Williams vs. Justin Fields Conundrum
No single decision will impact the landscape of the NFL in 2024, and beyond, than whether the Chicago Bears decide to forge ahead with Justin Fields, or chart a new course by selecting generational quarterback prospect Caleb Williams with the No. 1 overall pick in the NFL Draft.
To at least one current GM, the decision is an easy one.
“Caleb is as athletic as they come at that position,” an NFL general manager tells me. “He has super potential.”
Williams enters the NFL as one of the most heralded quarterback prospects of the past decade, with the Heisman Trophy in tow alongside a 66.9 career completion percentage with a whopping 93 touchdowns to just 14 interceptions.
Bears general manager Ryan Poles has the opportunity to alter the trajectory of what was once a proud, crown jewel of an NFL franchise, by selecting Williams first overall and can building around him with upwards of $79.7 million in cap space this offseason.
But, the possibility remains — albeit remote, that Justin Fields showed Poles enough during a 2023 season that saw him pass for a career-high 2,562 yards with 16 touchdowns and nine interceptions that at age 24 he can reach new heights and lead the Bears back to the promised land.
For the rest of the league, the palace intrigue is twofold.
If Fields returns, the Bears will in all likelihood trade out of the No. 1 overall pick in exchange for a king’s ransom for a second consecutive year and add significant draft capital to their war chest. The amount of teams that would storm the gates for the chance to draft Williams would be significant.
Meanwhile, if Poles believes Williams has a loftier ceiling than Fields, a young and electrifying quarterback who has rushed for 2,220 yards in 40 NFL games becomes available to the highest bidder.
Is there a better option, not named Caleb Williams for quarterback-desperate teams such as the Falcons, Steelers, Raiders, and Patriots, among others, on the outside looking in at the top of the draft order and of competent quarterback play than Fields?
The NFL Draft begins with the No. 2 selection this year, but the NFL offseason in some ways hinges on what the Bears decide to do at quarterback.
How The Tampa Bay Buccaneers Deploy the Franchise Tag
Buccaneers general manager Jason Licht is in an unenviable position.
Having already released Pro Bowl linebacker Shaq Barrett, and as I reported at FanBuzz, likely opting not to tag veteran linebacker Devin White, Licht, and the Buccaneers must decide how to handle the futures of All-Pro wide receiver Mike Evans, resurgent quarterback Baker Mayfield, and Antoine Winfield Jr., one of the rising young safeties in the sport who may already be the premier player at his position.
While the Buccaneers have approximately $43.9 million in cap space, those are still some expensive mouths to feed, who happen to be attached to players who will have robust markets if they somehow reach free agency.
Evans has surpassed 1,000 receiving yards each of his 10 seasons, and the wide receiver tag is slated to be $21.8 million this offseason.
Meanwhile, Mayfield seems to have found a home in Dave Canales’ offense, and with the Buccaneers’ supporting cast, passing for a career-high 4,044 yards with 28 touchdowns to 10 interceptions. However, Canales is now the Panthers’ offensive coordinator and the tag would guarantee Mayfield $38.3 million in 2024.
Finally, Winfield held opposing quarterbacks to a meager 68.9 passer rating during the 2023 season, while intercepting three passes and adding six sacks. Oh, Pro Football Focus happens to list Winfield as the No. 1 safety in the NFL.
“If I had to guess,” a prominent agent familiar with the Buccaneers’ thinking told me from Indianapolis and the Combine this week. “The Buccaneers will use the tag on Antoine Winfield Jr. He’s the most important of the bunch.”
Remember, teams can only use one franchise tag, even if they have a potential franchise quarterback, top-10 wide receiver in the league, and the NFL’s best young safety to re-sign in a single offseason.
Conventional wisdom would suggest the Buccaneers would love to keep Winfield Jr. in the pewter and gold for the foreseeable future, but, if Licht and Winfield’s representatives can’t reach a long-term contract, committing $16.2 million on the franchise tag seems like an easy — and palatable decision.
Whether the Buccaneers tag Evans or sign him to a long-term contract will shape the wide receiver market. Mayfield would immediately become one of the most coveted veteran quarterback options should he reach free agency. And, to say Winfield would have a robust market would be the understatement of the offseason.
“I loved Winfield when he was at Minnesota,” a veteran NFL scout told me this week. “I’d love it if we had the chance to sign him, but it sure sounds like Tampa’s trying to tag him.”
Licht and the Buccaneers have some major decisions to make, how Tampa deploys the tag will impact the top of three vital free-agent markets.
Will Stefon Diggs request a trade?
The wide receiver market is shaping up to be robust, even if its star power is a bit overshadowed by a historic crop of free-agent running backs.
Tee Higgins has been tagged by the Cincinnati Bengals, Mike Evans might be by the Buccaneers, same goes for Michael Pittman Jr. with the Colts, not to mention Calvin Ridley, Darnell Mooney, and Tyler Boyd are all set to become free agents in a few weeks.
Still, the best receiver available might be potentially up for grabs via trade.
After all, general manager Brandon Beane and the Buffalo Bills reside in the seventh ring of Salary Cap Hell. Somehow, Buffalo must shed $41.23 million in cap space to get under the cap before March 13.
One way to do so would be unloading star wide receiver Stefon Diggs.
Diggs is set to count $27.8 million against the cap in 2024, and Buffalo would save $19.05 million against the cap with a post-June 1 trade and an additional $22.4 million in 2025 while triggering an $8.8 million dead money charge for this offseason.
It isn’t often that a receiver with 9,995 receiving yards and 67 career touchdowns becomes available, but a Bills firesale may be necessary.
Just don’t count on teams banging down the Bills’ door to make a trade.
“It’s a smaller trade market for him than you’d expect,” an AFC Scouting Director tells me. “He’s a different personality. Has some up and down production years, but sees him self as one of the elite receivers. He’ll want big money, but his production may not match.”
Any Diggs trade would undoubtedly impact the receiver free agent market and perhaps take a team with significant cap space out of the running for one of the other top free agents at the position.
What Dak Prescott’s Eventual Contract Extension Looks Like
No decision matters more to the Dallas Cowboys’ present and future than how they handle Dak Prescott’s contract this offseason.
After all, not only does Prescott account for 22.3% of the Cowboys’ salary cap ahead of the 2024 new league year getting underway, but Dallas is currently $4.03 million over the cap. In a year where the Cowboys are all-in on Mike McCarthy and it might be an NFC Championship Game appearance or bust for the head coach.
CBS’ Joel Corry believes Prescott could reset the market, on an extension that could average $60 million per season.
According a prominent NFL agent, who was granted anonymity to speak freely about a client he doesn’t represent, Prescott holds all the cards.
“If Dak is comfortable financially and is okay to approach this seeking a team-friendly deal so they can keep building around him then that’s one approach to take.” The agent tells me. “But, if it were me, and he wants every penny he is entitled to, then you go to war and get every last penny.”
The agent echoes Corry’s sentiments and believes that not only is $60 million the likely destination of these talks, but a very reachable conclusion to them.
But, former NFL Executive of The Year winner, Jeff Diamond, tells me he doesn’t envy the position Jerry Jones and the Cowboys find themselves in.
Diamond believes there’s a blueprint for what Prescott’s deal ultimately winds up looking like.
“Dak has tremendous leverage because the team has to get a deal done,” Diamond says. “They probably have to do a four-year extension for between $210-220 million with a $50 million signing bonus pro-rated over five years and a low 2024 cap number to around $24 million in total to save them about $31 million against the cap this offseason.
“The guarantee probably be about $200 million. That’s pretty strong for a really good regular season quarterback, but not so great in the postseason, with a 2-5 playoff record and coming off a bad loss to the Packers.”
What Prescott’s deal ultimately winds up looking like will play a major role in how aggressive the Cowboys can be in free agency, and whether the likes of Tyron Smith, Stephon Gilmore, Jayron Kearse, etc., are back in Dallas next season.
Will the Houston Texans go All-In?
The Houston Texans were among the biggest surprises of the 2023 season, but don’t dare call DeMeco Ryans’ team a one-year wonder.
Houston has staying power, thanks not only to Ryans’ hyper-competitive culture, and franchise quarterback C.J. Stroud’s sky-high potential entering just his second season but also because of the promise that the $70 million in cap space at Nick Caserio’s disposal to fortify an exciting young core.
“The big thing (coach) DeMeco (Ryans) and I have talked about on a consistent basis is just trying to build as deep and consistent a roster top to bottom (as possible),” Caserio told reporters at the NFL Combine in Indianapolis.
The Texans have a legitimate Super Bowl window for at least the next three seasons, with Stroud playing under his rookie deal and Houston in a very winnable AFC South, but how aggressive will Caserio be in free agency?
Since only the Washington Commanders, Tennessee Titans, Chicago Bears, and Caserio’s old friends with the New England Patriots have more spending flexibility, expect the Texans to shop at the top of the market—especially when it comes to pass-rushers. With a loaded running back market, can you imagine Saquon Barkley sharing a backfield with Stroud? And they'll continue to build out a secondary in Ryans’ image.
Houston’s aggressiveness won’t just determine which players are available for the rest of the league but could drive up the asking price at some positions if Caserio comes out swinging in the early days of the new league year.
Because of its young nucleus that’s led by Stroud, who may already be a top-10 quarterback in this league, the Texans may just win the offseason and parlay big signings into a legitimate Super Bowl run. How often has that happened?
I feel like ditching Fields is the obvious choice but it is the Bears... Sigh.