New York Jets
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New York Jets fans walk this Earth in a special category thanks to heartbreaking moments throughout organization history that have stunned.

Robby Sabo

Torture is a loaded word designed for no one. As true as the statement remains, New York Jets fans wholeheartedly disagree.

For decades, Jets fandom has remained in a special class only a couple of groups can resonate with (Kansas City Chiefs and Minnesota Vikings). Heartbreak and disappointment have rung true since 1969.

Actually, it’s tough to narrow down the greatest heartbreaks to only 11 but today, it’s been done while crying throughout the entire process.

11. Bill Belichick bolts

This particular list is about gut-punches. We’re looking for in-the-moment horrific scenarios. When Bill Belichick bolted for New England after the 1999 season, it certainly hurt. But nobody thought it would alter the course of NFL history to such a degree.

From a historical standpoint, Belichick is No. 1. In terms of in-the-moment heartbreaking situations, the Belichick situation starts the list at No. 11.

10. Ken O'Brien over Dan Marino

Similarly to Belichick, the Ken O’Brien over Dan Marino draft situation falls into more of historical relevance. There’s no question the feel in the room was that of confusion; Marino was the coveted gunslinger.

In the end, O’Brien enjoyed a solid career, most likely ranking as the second-greatest quarterback in Jets history. Marino never won a chip, and although he tortured the Jets for a career, the punch in the gut wasn’t as stark as some of the coming examples.

Marino ranks ahead of Belichick for one simple reason: the shock of the moment was heavier. Remember, Belichick was a failed NFL head coach.

9. Chad Pennington preseason injury vs. Giants

On the heels of an AFC East title (the last to this very day), the 2003 Jets were ready to roll. Then Chad Pennington broke bones.

In a meaningless preseason game against the big-brother New York Giants, Pennington was hit only to fall on his right arm and break himself. He missed the first three games of the season and a once-promising season turned into a 6-10 nightmare.

It hurt badly due to the idea Pennington served as the new, young franchise quarterback.

8. Kyle Brady over Warren Sapp

Kyle Brady over Warren Sapp ranks higher than Belichick and Marino due to one simple factor: the moment was more egregious.

The sheer volume of anger was massive. Fans understood. Pundits sympathized. It was a wild choice.

7. Orchard Park, 2015

A 10-5 mark during Todd Bowles‘s rookie season placed them in Orchard Park, New York with a chance to go to the tournament for the first time in five seasons.

It was not to be.

Ryan Fitzpatrick struggled but worse was the defense’s performance. Sheldon Richardson and Muhammad Wilkerson attempting to play the edge as 300-pound defenders turned laughable. Bowles was forced in such a situation thanks to the drafting of Leonard Williams the prior spring.

The entire team laid an egg in the game Bowles will be remembered most in Jets lore.

6. Brett Favre 8-3 collapse, 2008

The Jets turned dominant when they went into Tennessee and knocked off a nasty Titans team, improving to 8-3 on the season. Brett Favre led a dominant rushing offense led by Nick Mangold and D’Brickashaw Ferguson up front.

The defense also held its own. Eric Mangini and Mike Tannenbaum, successfully throwing together one of the most talented rosters in the NFL were on the brink of something special.

Then the Jets happened. Favre played with a big-time injury as the team lost four of its last five games. The capper? Former friend Chad Pennington came into the swamps of New Jersey in Week 17 to cement his Miami Dolphins AFC East title.

5. Doug Brien, 2004

Not one, but two; Doug Brien ripped the heart out of the entire fan base with two playoff kicks.

First, a 47-yard try with just over two minutes to go in a tie game clunked off the crossbar. After an Eric Barton interception, Brien faced a mere 43-yarder that would send the Jets to the AFC Championship Game.

He missed.

The Jets didn’t touch the ball again and the Pittsburgh Steelers took it in overtime. After such an impressive performance in San Diego the week before, the energetic run came crashing to a sudden halt.

4. AFC Championship Game, Pittsburgh

The 2009 AFC title game was child’s play compared to 2010. Against the Indianapolis Colts, it was clear the Jets weren’t ready. During the 11-5 campaign coming off a beatdown of the New England Patriots, all was there, ripe for the picking.

Never have the Jets came out as flat in a crucial game than they did on that Sunday afternoon. Falling behind by three possessions early, Mark Sanchez and the offense scratched and clawed its way back yet it wasn’t enough.

3. A.J. Duhe

Five interceptions thrown by Richard Todd, three to Miami Dolphins linebacker A.J. Duhe—it’s the stuff that creates nightmares.

Don Shula knew he had to slow down the fast-paced Jets so he tampered with the Miami turf. It worked. New York was terrible in the 1982 title game and fell flat, losing 14-0.

2. Vinny's Achilles

The 1999 season represented the most celebrated preseason Jets team of all-time. Never have pundits been in such agreement that this roster represented the Super Bowl favorites.

When Vinny Testaverde blew out his Achilles at home early in Game No. 1, everything was lost.

Tom Tupa entered the game and the Jets started 1-6. Eventually, Ray Lucas took over and Bill Parcells’s amazing coaching job resulting in an 8-8 season wasn’t lost on anybody. Still, Vinny’s Achilles knocked the wind out of an entire group of green.

1. AFC Championship Game, Denver

This is was their moment. This was their chance. The 1998 AFC title game, to this day, remains this organization’s best chance at glory.

The Jets would have beaten the Atlanta Falcons in the Super Bowl.

Up 10-0 with a little under 12 minutes to go in the third quarter, the Jets were on the brink of a mind-boggling franchise turnaround. It was almost too much to grasp.

On Denver’s very first offensive play after the blocked punt that led to the Cutis Martin score, John Elway found a wide-open Ed McCaffrey on the post after Victor Green and Otis Smith blew the two-deep coverage.

On the very next kickoff after a score, the Jason Elam kickoff ended short thanks to the wind. It inexplicably bounced up only to be recovered by the Broncos. When has any NFL fan witnessed such craziness? Only the Jets.

After a field goal, knotting the game up at 10, it was over. The entire team had its will completely taken from their souls. It ranks as the most heartbreaking moment in New York Jets history by a mile.

Robby Sabo is a co-founder, CEO and credentialed New York Jets content creator for Jets X-Factor - Jet X, which includes Sabo's Sessions (in-depth film breakdowns) and Sabo with the Jets. Host: Underdog Jets Podcast with Wayne Chrebet and Sabo Radio. Member: Pro Football Writers of America. Coach: Port Jervis (NY) High School. Washed up strong safety and 400M runner. SEO: XL Media. Founder: Elite Sports NY - ESNY (Sold in 2020). SEO: XL Media. Email: robby.sabo[at]