10 most heartbreaking losses suffered in NY Jets history

3. The NY Jets' double OT playoff loss to the Browns in the 'Marathon by the Lake'

For longtime Jets fans, this is the one game that forever haunts their memories. The Jets' excruciating four-hour, 23-20 double-overtime loss in the divisional playoff round to the Cleveland Browns on January 3rd, 1987.

In the post-Super Bowl III world, the 1998 and 2010 New York Jets are considered by many to be the two best single-season teams in franchise history. Rightfully so, but the 1986 Jets are firmly in the discussion as well.

Back then, this Jets team was coming off an 11-win season in 1985, and in '86, the team raced out to a 10-1 start. New York had an extremely balanced attack on both sides of the ball.

On offense, the Jets had a Pro Bowl quarterback and running back from the year prior in Ken O'Brien and Freeman McNeil to go along with one of the league's best deep threats ever in wide receiver Wesley Walker and other Pro Bowl players in wide receiver Al Toon and tight end Mickey Shuler.

Defensively, the Jets "New York Sack Exchange" with Mark Gastineau and Joe Klecko continued to wreak havoc on opposing defenses.

The All-Pro pass rushers were the 1986 equivalent of Myles Garrett and Aaron Donald — two dominant forces. Linebacker Lance Mehl also had a career year in '86, making the Pro Bowl. So there was no shortage of impact players on the Jets that season.

But after storming out the gate in 1986, injuries hit the Jets hard, and the team faltered down the stretch. The Jets would lose their last five games to fall to 10-6 as they subsequently lost position atop their division and the AFC.

They entered the playoffs as a wild card team, and doubt started to creep in. But the Jets would begin to erase that doubt, blowing out the Kansas City Chiefs at home 35-15 in the first round of the playoffs.

To shake things up and halt the losing skid, quarterback Ken O'Brien was benched in favor of Pat Ryan. O'Brien would return to the lineup a week later to relieve an injured Ryan. 

The following week in Cleveland, it wasn't a pretty game by any stretch. Both teams struggled mightily to move the football, but with 4:14 left in the contest, Freeman McNeil broke a 25-yard touchdown run, giving the Jets a 20-10 lead.

Up two scores, with time winding down, the Jets were on the verge of advancing to the AFC Championship Game to play the Broncos, a team the Jets had easily defeated earlier in the season.

It was easy to foresee a potential New York vs. New York Super Bowl scenario, and the Giants would eventually win Super Bowl XXI 39-20 over the Broncos.

But as great as the Giants were in '86, Jets fans knew that they were fully capable of beating any team in the league at their peak during that season. 

Unfortunately, on this dreadful Sunday in Cleveland, the Jets found a way to beat themselves and break their fan base's hearts.

Down 10 points, Browns quarterback Bernie Kosar led a frantic comeback, thanks to the most infamous penalty in Jets history.

Facing a 2nd-and-24, backed up on their own 18-yard line, former NFL Defensive Player of the Year Mark Gastineau, who had 2.5 sacks on the day, roughed up Kosar after an incompletion and was flagged for roughing.

The penalty would give Cleveland new life, and Kosar captained the Browns' offense to New York's one-yard line as the two-minute warning hit. A Kevin Mack touchdown run with 1:57 remaining would cut the Jets' lead to 20-17.

Despite still having two timeouts, Cleveland would unsuccessfully attempt an onside kick. The Jets' Marion Barber would recover the football on the Browns' 45-yard line. In typical Jets fashion, the team botched the sequence of events that ensued.

New York ran two running plays that barely got back to the line of scrimmage, but they accomplished the goal of forcing the Browns to use their remaining timeouts. However, on third down, with 1:48 left, the Jets inexplicably ran a pass play where Ken O'Brien was sacked.

By rule, back then, any sack in the last two minutes of a game, the clock would stop until the ball was reset. By not running the ball, New York lost the opportunity to take more time off the game.

Despite all this, the time and field position was still on the Jets' side. After punting the ball away, the Browns would get the ball back on their own six-yard line with 1:03 remaining, having no timeouts, only needing a field goal.

But hold up, the Jets were called for holding on the punt. So the Browns would accept the penalty and force New York to punt again. Cleveland's strategy paid off as a punt return would get them out to the 32-yard line.

During this sequence, more time had come off the clock, down to 53 seconds, but the Browns had gained nearly 30 extra yards, setting themselves up with a shorter field to get into field goal range.

The catch, however, was that their kicker Mark Moseley had already missed two field goals. So a field goal of any length was no sure thing, which would prove out later.

The Jets' comedy of errors in their collapse continued on Cleveland's very first play from scrimmage. The Jets would be called for a 26-yard pass interference penalty that instantly put the Browns near field goal range at the 42.

One play later, Bernie Kosar would connect on a deep pass to Webster Slaughter down to the Jets' five-yard line. With the clock ticking away rapidly and the Browns excessively celebrating the big play, Kosar would rush his team to the line of scrimmage and throw a near-interception in the end zone to Jets defensive back Russell Carter.

The Jets almost won the game in the hysteria, and Cleveland dodged a bullet. With 11 seconds left, the Browns opted to kick the short game-tying field goal rather than attempt another pass into the end zone.

With the game tied at 20 heading into overtime, the torture would continue for the Jets. New York's offense couldn't get anything going in the extra session despite having several opportunities to win the game in overtime.

The Jets even got a gift when the Browns drove all the way down to their six-yard line in the first overtime. Still, Moseley missed a 23-yard field goal wide to the right.

Sudden death became an inevitable and prolonged one for the Jets as Mark Moseley connected on a game-winning 27-yard field goal in the second overtime.

In sports, one team's misery is another team's fortune. Even though Cleveland would suffer a heartbreak of their own eight days later against Denver in the AFC Championship Game, the Browns' triumphant comeback against the Jets is one of their franchise's greatest moments.

On the flip side, It was one of the darkest days in the history for the New York Jets and still is.