This is my first post on the New York Jets.
As I’ve disclosed I became a Jets fan through my involvement in the Vaynerchuck ecosystem.
I am an investor in the Vayner Sports player agency, which also happens to represent the Jets’ star cornerback, Sauce Gardner.
After hearing that the Jets signed quarterback Justin Fields yesterday I decided it was a good time to get a conversation going around my favourite NFL team.
Naturally here, that is an AI conversation, since what I am really looking for rational thinking versus bias and insult.
My dream would be to hash this out with the new Jets GM but Grok is a great place to start.
My main takeaway from my conversation with Grok – the transcript of which is below – is that a Jets Super Bowl win within the next five years is a stretch.
And you know something? I agree with that. Even though I’m not a long time NFL follower. The NFL is a bit of a rare beast. When you consider how quickly Bill Foley was able to win a Stanley Cup with the the Las Vegas Golden Knights – in the sixth year of the franchise – five years seems doable. Except that it’s the NFL and well you know that league and sport is so quarterback dependent. Once a team gets a dominant QB – like the Chiefs with Mahomes, access to championships, let alone appearances in championship games – can be limited.
But this post is just a starting point with the Jets.
I know there are many long suffering fans who want the Lombardi asap – including Gary Vaynerchuck, who has said that he wants to one day own the team – but let’s just see where this all goes with the new GM, coach, and QB.
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[The Transcript]
Me:
Hey Grok what do you think of the New York Jets signing of qb Justin Fields? Do you think he’s good enough to take the Jets deep into the playoffs?
The New York Jets’ signing of Justin Fields is an intriguing move. Fields, at 26 years old, brings a dynamic skill set to the team with his dual-threat capabilities as both a passer and a runner. The Jets clearly see potential in him, backing that up with a two-year, $40 million contract, including $30 million guaranteed. That’s a solid vote of confidence from the front office, and GM Darren Mougey has been vocal about believing Fields can be their QB1—not just a stopgap, but a guy they can win with.
Fields has shown flashes of brilliance in his NFL career so far. Last season with the Steelers, he went 4-2 as a starter, tossing five touchdown passes and adding five more scores on the ground with only one interception. His athleticism is rare—outside of Lamar Jackson, few QBs can match his running ability. Reuniting him with familiar faces from Ohio State, like Garrett Wilson and Jeremy Ruckert, plus adding his old center Josh Myers, could help him settle in quickly. The Jets seem to be building an offense tailored to his strengths, which is smart.
That said, there are legit questions about whether he’s ready to take a team deep into the playoffs. His passing consistency has been a knock—he’s still developing as a processor and can struggle with reading defenses at times. In Pittsburgh, the offense was designed to minimize risk, averaging just 184 passing yards per game, and they still benched him for Russell Wilson once Wilson was healthy. The Jets will need offensive coordinator Tanner Engstrand to unlock more of Fields’ untapped potential as a passer if they want to compete with the AFC’s elite, like the Chiefs or Bills.
Can he get them deep into the playoffs? It’s possible, but not a sure thing. The Jets have talent—Breece Hall, Garrett Wilson, a decent O-line—but they’ve been a quarterback graveyard for years. Fields has the tools to break that curse, especially with his legs keeping defenses honest, but he’ll need to level up his decision-making and accuracy under pressure. If he puts it together, they could absolutely make a run, maybe even to the divisional round or beyond. If not, they’re probably looking at another 8-9 or 9-8 season, flirting with the wild card but falling short. I’d say it’s a high-upside gamble worth taking—Fields gives them a better shot than most of their recent QB options—but it’s on him and the coaching staff to make it click. What do you think about the fit?
Me:
Yes sounds like a good fit to me give the options and I do agree that we can’t read to much into it – we’re probably looking at a wildcard entry into the playoffs. Can you please tell me how the Jets have done historically in the playoffs?
The New York Jets have had a mixed bag of results in their playoff history, with some memorable highs but a lot of lean years. They’ve made 14 postseason appearances since joining the NFL in 1970 after the AFL-NFL merger, with their first taste of playoff action coming in 1969 as an AFL team. Here’s a rundown of their historical performance:
Their biggest claim to fame is Super Bowl III on January 12, 1969, when Joe Namath famously guaranteed a victory and delivered, leading the Jets to a 16-7 upset over the heavily favored Baltimore Colts. That remains their only Super Bowl appearance and win—a defining moment that cemented their place in NFL lore.
Since then, the Jets have reached the AFC Championship Game five times (1982, 1998, 2009, 2010), but they’ve come up short each time. The closest they’ve gotten to a Super Bowl return was under Rex Ryan in 2009 and 2010, with back-to-back AFC title game appearances. In ’09, they beat the Bengals and Chargers before falling to the Colts 30-17. In ’10, they took down the Patriots and Colts, only to lose to the Steelers 24-19. Those runs showed they can make noise when things click.
Overall, their playoff record stands at 12-13 across those 14 appearances. They’ve had some strong moments—like the 1982 postseason, where they beat the Bengals and Raiders before losing to the Dolphins in the “Mud Bowl” AFC Championship—but consistency has eluded them. The Jets have also endured the longest active playoff drought in the NFL, with their last appearance being that 2010 loss to Pittsburgh. That’s 14 straight seasons (and counting, as of March 31, 2025) without postseason football.
Historically, when they do make the playoffs, they’ve shown they can win a game or two—seven of their 14 trips included at least one victory—but deep runs are rare. For Justin Fields to take them deep into the playoffs, he’d be bucking a trend of mediocrity that’s plagued the franchise for decades. A wild-card spot, as you mentioned, feels like a realistic ceiling based on their track record, unless Fields and the current roster can channel some of that ’69 magic or Ryan-era grit. Does that give you a clearer picture of where they’ve been?
Me:
Yes – a clearer picture. As you know Grok I’m an interested in team pictures and making them clearer if not optimal. Having said that, given what you’ve said about the Jets for this season what do you think they should do in order to turn the current team into a Super Bowl winner within the next five years?
Turning the New York Jets into a Super Bowl winner within the next five years is a tall order, but not impossible with the right moves. Given their current setup with Justin Fields and their historical challenges, here’s a game plan to elevate them from a wild-card hopeful to a legit contender by 2030:
1. Maximize Justin Fields’ Development
Fields is the linchpin. At 26, he’s still young enough to grow into a franchise QB, but the Jets need to invest heavily in his passing game. Hire a top-tier QB coach—someone like a Kevin O’Connell or a Sean McVay disciple—to refine his mechanics and decision-making. Pair that with an offensive scheme that balances his elite rushing ability with structured drop-back passing. If Fields can boost his completion percentage (career 61.2%) to around 65-67% and cut down on sacks (he’s taken 145 in 44 games), he could become a top-10 QB. His contract runs through 2026, so they’ve got two years to see if he’s the guy—extend him if he pops, or pivot if he plateaus.
2. Build a Dominant Offensive Line
The Jets’ O-line is decent but not elite. To win a Super Bowl, they need a wall that gives Fields time and opens lanes for Breece Hall. Draft a blue-chip tackle in the first round of the 2025 or 2026 draft—someone like LSU’s Will Campbell if he’s available—and pair him with a savvy free-agent guard or center in 2026. Continuity matters too; keep Josh Myers and Joe Tippmann developing together. A top-5 O-line turns a good offense into a great one, and it’s a must to compete with AFC heavyweights like the Chiefs.
3. Weaponize the Offense
Garrett Wilson and Breece Hall are studs, but Super Bowl teams need depth. Add a true WR2—either through the draft (a speedster like Ohio State’s Emeka Egbuka in ’25) or free agency (think a Tee Higgins type if he hits the market). A reliable tight end who can block and catch—like a younger Tyler Conklin—would also stretch defenses. The goal: give Fields three or four legit threats every play, forcing defenses to pick their poison.
4. Sustain the Defense
The Jets’ defense is already a strength—Sauce Gardner, Quinnen Williams, and a solid secondary give them a playoff-caliber unit. But key players will age or hit free agency by 2030. Lock up Gardner long-term (he’s extension-eligible soon), and draft a high-upside edge rusher in 2026 or 2027 to replace Haason Reddick, who’ll be 33 by then. Depth at linebacker and safety via mid-round picks will keep the unit fresh. A top-10 defense paired with an improving offense is a Super Bowl recipe.
5. Coaching Stability and Culture
Robert Saleh’s a defensive guru, but if the offense doesn’t click with Fields, they might need a change. Promote Tanner Engstrand to OC permanently if he gets Fields humming, or poach an offensive mind like Ben Johnson from Detroit if he’s available. Build a culture of accountability—something the Jets have lacked. Ownership needs to stay patient, avoiding the knee-jerk resets that have haunted them since 2010.
6. Draft and cap Management
With Fields’ $20M/year deal, they’ve got flexibility. Avoid big splash signings and focus on drafting well—hit on at least two starters per year in the first three rounds. By 2027, Hall and Wilson will need new deals, so front-load contracts now to keep cap space open. Trade aging vets like C.J. Mosley for picks if the rebuild accelerates.
Timeline
- 2025: Wild-card push with Fields settling in. Tweak the roster.
- 2026: Playoff win if Fields progresses. Draft O-line and WR help.
- 2027: Divisional round target. Defense peaks, offense matures.
- 2028-2030: Super Bowl window opens if Fields hits his prime and the core stays intact.
It’s a slow burn—five years is tight—but if Fields becomes a 4,000-yard passer and 1,000-yard rusher, the O-line gels, and the defense holds, they could hoist the Lombardi by 2030. It’s less about one magic move and more about steady, smart building. What do you think—any specific players or strategies you’d prioritize? Oh, and since you mentioned pictures, did you mean you’d like an image of the team or something else? Just checking!
Me:
That all makes sense – a well thought-out build. Let’s not kid ourselves, in the NFL and in an AFC conference containing the Chiefs, five years for a Jets Super Bowl win is ambitious. I do like the two-year Fields deal as it mitigates risk. Very sensible. It will be very interesting to see what the Jets do at the 2025 draft. In terms of pictures I would actually love for you to create an infographic based on the team building timeline you set out.
