The beautiful disaster that is the Cleveland Browns

Will the Browns finally win a game? (0:42)

Damien Woody and Darren Woodson discuss if the Browns can break their losing streak Sunday against the Bears. (0:42)

On a Sunday of little relevance, in a season already over, Hue Jackson finally broke down. He had a dream the night before, fast asleep in his hotel bed, that his Cleveland Browns won a football game. Jackson woke up and couldn't wait to get to the stadium that morning. It was a great week of practice, and there were signs -- you had to look for them, but they were there -- that this would be the day the losing skid would end.

The game was at Cincinnati, a place where Jackson spent seven seasons as an assistant, and how great would it be, he thought, to win in front of old friends?

But the Browns didn't win, because they are, of course, the Cleveland Browns. They lost by two touchdowns. Players tramped to the locker room and knelt for the Lord's Prayer. It was Nov. 26, Cleveland was 0-11, and two years of failed efforts and public humiliations raced through the coach's head.

Jackson has always considered himself a positive person, the right man for a job that has seen six coaches in 10 years. But when the Our Father ended and the players rose to their feet, Jackson could not get up. He looked as if he might cry. A couple of players walked over to him.

"All right, Coach," one of them said. "We got you."

They picked him up off the floor.

The plan was to tell the story of how a lovable-loser franchise was changing its culture through the use of analytics and a massive infusion of youth. We'd follow 10 rookie draft picks through their first NFL season and get a glimpse behind the curtain along the way. The Browns, however, wanted to hold off on providing access until they recorded their first victory of the season.

There was good reason for optimism at the start of the season in Cleveland. The franchise had drafted Myles Garrett at No. 1, and the defensive end was considered a once-in-a-generation talent. There was hope at quarterback, too, with rookie DeShone Kizer coming. Curious crowds filed in to training camp in Berea, Ohio, and Jackson was fired up. He ordered the team to do up-downs, something you see more in high school practices. It was a message that the Browns were going to do whatever it took to get better.

But true to form, the plan has fallen to bits. Garrett hurt his ankle and missed the first month of the season. Kizer amassed a league-high 19 interceptions. And the cornerstone of the team, All-Pro tackle Joe Thomas, tore his triceps. Cleveland still hasn't won a game, and on Dec. 7, Browns co-owner Jimmy Haslam fired executive vice president Sashi Brown, largely ditching the Moneyball strategy after 23 months.

For the fourth time in five years, the Browns are starting over again.

"I never set out to lose at anything I do," Jackson said. "And when you can't seem to win, it's like you're in a maze and you keep coming back to the same outcome.

"Do I think anybody and everybody can do this? No, I don't. I really don't. You've got to have some strength and you've got to have some total belief in yourself in order to do this. Because it will test you, it will challenge you, and you will question yourself."

December in Cleveland can be brutally unpleasant. The wind whips up over Lake Erie, making a 20-degree day feel as if it's the coldest you've been in your entire life.

Inside FirstEnergy Stadium, it's even more miserable. The Browns are 0-14. They are the only team, according to ESPN Stats & Information, to start consecutive seasons with that record. They have lost 32 of their past 33 games. Because they close the season at Pittsburgh, this weekend's game at Chicago would seem to be their best hope to avoid becoming just the second team to go winless in a 16-game season. That Sunday's game falls on Christmas Eve bodes well for the Browns, as Jackson's only two wins in his past 32 games as a head coach have come on Dec. 24.

Those who know the team aren't getting their hopes up. A month ago, one Browns fan started planning a "Perfect Season" parade in the event the team goes 0-16 -- and even got a permit for it. The parade is set for Jan. 6.

"Whenever I hear players say, 'Why do bad things always happen to us?' I'm quick to point out that it is not a tangible thing," Thomas said. "We are the ones that make good or bad things happen."

There are many that's-so-Browns moments in 2017, snapshots of failure so inexplicable that you know it could happen to only one team. But perhaps the biggest embarrassment of the season came in early November, when Cleveland tried to trade for Cincinnati Bengals backup quarterback A.J. McCarron. The deal was done, but the Browns didn't turn in the paperwork on time.

Quarterback, or lack thereof, has been the Browns' biggest source of angst for nearly two decades. They have tried 20 different starters at the position since 2007. So imagine the sheer anger that flows through the city every time Carson Wentz is on Monday Night Football or a highlights show. Before his recent knee injury, Wentz had emerged as one of the best quarterbacks in the NFL this season, an MVP candidate. And he could have been a Cleveland Brown.

The team held the No. 2 pick in 2016, when Wentz and Jared Goff were in the draft. Jackson had extensive conversations with Wentz in the months leading up to the draft, and by all accounts, Wentz was ready to be a Brown. The team sent him part of its playbook, and he studied it voraciously, hoping to impress Jackson and the front office. He had regular conversations with Jackson by phone and made it clear he was quickly picking up the Cleveland offense. (The playbook was printed on Jackson's stationery.)

Twice a day, Wentz would go over the Browns' plays on the whiteboard in North Dakota State's film room with Ryan Lindley, a former NFL quarterback who was mentoring him before his pro day. When friends and fans bumped into Wentz in Fargo, they would often express hope he wouldn't end up in Cleveland. But Wentz always politely brushed those worries aside and made it clear he was ready to embrace the challenge of helping rebuild the Browns. Lindley teased him that if he succeeded in Cleveland, so desperate for a winner, the city would put him on its version of Mount Rushmore.

When one of his college coaches showed Wentz an Instagram picture of a high school kid in North Dakota wearing a Browns jersey with WENTZ on the back, the quarterback thought it was cool. He was even considering getting a Browns tattoo. The morning of his pro day, Wentz met with Jackson and former QB coach Pep Hamilton for an hour, admitting he'd barely slept because he was up late, anxiously studying their playbook like he was prepping for a final exam.

After he put on an impressive performance during his pro day, Wentz felt confident he'd shown them he was worthy of becoming the second pick in the draft. No other team had sent a head coach to Fargo to watch him throw.

Wentz never got the chance to find out what he could do in Cleveland. The Browns, intent on stockpiling draft picks, traded the spot. Cleveland's front office later stated he wasn't one of the top 20 players in the draft. Wentz went on to change the fortunes of the Philadelphia Eagles, who are 12-2 and have clinched the NFC East and a first-round playoff bye.

When asked last week whether he had wanted Wentz and gotten vetoed by the front office, Jackson declined to comment.

"He plays for the Philadelphia Eagles; we moved on, and the young man is doing great," Jackson said. "And I think that's all that matters."

Jackson did acknowledge that one of the biggest issues for the Browns this season is their lack of experience at the most important position in the NFL.

"You're talking about a young team led by a young player," Jackson said. "We hoped, and we were very realistic, that things could be better. But at the same time, we kind of knew that it might not go the way we wanted it to. You know, sometimes it just doesn't happen the way you think it's going to happen."

They're almost forgotten now under the avalanche of losses, but there have been some near-misses this season. On opening day, Kizer rallied the Browns before Pittsburgh hung on for a 21-18 victory. Steelers coach Mike Tomlin was obviously annoyed after the game. As he walked into the tunnel, he looked at a group of reporters and said, "Great to play s---ty and win."

Kizer completed 20 of 30 passes for 222 yards that day and showed flashes of goodness. After the game, Jackson said the 21-year-old gave him hope.

The Browns nearly beat the Titans and the New York Jets and probably should have won at Indianapolis in Week 3. If they could have pulled off one of those wins, rookie safety Jabrill Peppers has wondered, would the season be different?

"It's like we're right there," Peppers said. "We're right at the hill.

"Finding ways to win in the fourth quarter, that's the name of the game in this league. We are slowly getting to a point where the young guys are understanding the significance of it."

In search of inspiration, Jackson invited retired boxing champ Andre Ward to speak to the team when the Browns were in Los Angeles earlier this month. Ward talked about opportunity and told the players their time is coming. And when it does, they have to be ready.

The Browns locker room doesn't really have the anticipated toxic air of a winless team. Linebacker Joe Schobert figures it's because there are so many first- and second-year players who feel as if they're in this together. They have not been around long enough to get lured into believing in curses.

Many of the Browns veterans are gone, but the ones who are left seem to integrate well with the young players. Thomas, for example, went on injured reserve in October but is more visible in the locker room now than when he was playing. He sits in meeting rooms and helps coach the offensive tackles, and shares notes he accumulated from years past. He also provides scouting reports for the defensive ends.

"I love being around Joe because he tries to take care of the young guys," Garrett said. "He sticks around for whoever wants to listen. I rely on him every week, not only on my notes but his notes to come together and see who I'm going up against."

The Dec. 10 game between the Browns and the Green Bay Packers was dubbed by a local radio personality as the dawn of a new era. John Dorsey had been hired three days earlier, and the city was abuzz. Dorsey's previous job was as general manager for the Kansas City Chiefs. In his first season, he took a team that finished 2-14 the year before and made it to the playoffs. Maybe he could fix the Browns.

The game would be played without Green Bay quarterback Aaron Rodgers, so experts picked this as the best chance for Cleveland to finally win. The day got off to an energizing start. Josh Gordon, fresh off a long ban for violations of the league's substance abuse policy, caught an 18-yard touchdown pass and celebrated by donning a pair of dark sunglasses. It was cloudy.

By the end of the third quarter, the Brown weren't just winning. They had a 14-point lead. TV cameras panned to Dorsey and Haslam sitting together. Hope wasn't just in the air; the city of Cleveland was choking on it.

But in the fourth quarter, the game began to unravel. There was a hands-to-the-face penalty, an interception and a punt return. The Packers tied the score with 17 seconds to play. By then, it might as well have been over.

On the Packers' first possession of overtime, Brett Hundley hit Davante Adams for a 25-yard touchdown. The crowd wasn't necessarily stunned. This is what happens in Cleveland. A bitter wind cut through the stadium, raising the obvious question: Why would anyone subject themselves to this?

Christian Lugo, a longtime member of the Dawg Pound, almost didn't go to the game. He wasn't feeling well, knew it would be cold and decided to give away his seat. But then he started thinking about how he hadn't missed a home game since 1999, so he bought another ticket for $50 and went to the game.

He didn't want a Packers fan taking the seat. (The stadium was half-empty.) But mostly, he went because he thought that could be the day things finally turned around in Cleveland.

It wasn't.

"Everything here is hard," Lugo said

Dorsey, dressed in slacks and an overcoat, sat in a corner stall of the locker room late that afternoon, taking in the scene. He wanted to see how this team reacted to another loss.

The new GM caused somewhat of a stir last week when he went on a local radio show and said the past front office "didn't get real players," which would seem like a slam on his new team.

"I may have misspoke a little bit," Dorsey said during a phone interview Monday. "I'm man enough to say it. I'm not an English major. What my heart was wanting me to say is we have some young players here. We just need more young players."

Dorsey was a linebacker for the Packers in the 1980s and has a deep respect for the passion of Cleveland's fan base. He says he wants to "reawaken the sleeping giant."

He spent six months out of football when he and the Chiefs parted ways this past summer. He didn't know what it was like to have that much time on his hands, so he forced himself to follow a routine. Dorsey devoted the early-morning hours to his Catholic faith, then would go to the gym. By 11 each morning, he'd head down to his makeshift office in the basement to watch film and call people around the league. He wanted to be ready if he had another chance in the NFL.

Now he has so many decisions to make. The Browns have six of the top 65 picks in the 2018 draft and would land the No. 1 pick with a loss at Chicago or a win by the New York Giants against the Arizona Cardinals. Cleveland is expected to have two picks in the top six.

Maybe the Browns will draft UCLA QB Josh Rosen or USC's Sam Darnold. Or Dorsey could make a Wentz-like pick and go for Wyoming's Josh Allen.

It sounds almost impossible that Cleveland could finally find the one thing that two decades of coaches couldn't. It could get its marquee quarterback.

But before that, the Browns have to get through this long winter. Dorsey will observe the final days of their season and decide where they need to go next. He'll compile his observations and share them with the coach, who presumably will be Jackson.

In their news release announcing Dorsey's hire, the Haslams announced that Jackson will be back next season. Dorsey says he has been struck by how hard the team plays for Jackson.

Some days, the players are what keep Jackson going. It has been rumored that the Bengals might want him to replace longtime coach Marvin Lewis, but Lewis is still currently employed by Cincinnati, and Jackson told reporters last weekend that he's committed to Cleveland and wants to see this whole thing through.

"I truly believe there is winning in there," Jackson said. "I just think we've got to go bring it out.

"We're closer now than we've ever been."

ESPN senior writer Kevin Van Valkenburg contributed to this report.