After going 1-4 in his last five fights, former UFC middleweight champion and long-time middleweight contender Chris Weidman is on the hunt for greener pastures in the 205-pound light heavyweight division.

The 35-year-old will make his debut in the new weight class during the main event of the UFC on ESPN 6 card Friday night in Boston when he takes on the undefeated Dominick Reyes.

But will Weidman's move up unfurl the way he thinks it will? That is far from certain.  

Despite the scale of the task in front of him, he is already looking forward to a fight with light heavyweight champion Jon Jones. 

"I don't think [Jones has] looked that good. I don't think he's looked as dangerous. He's not finishing, and I see there's a lot of—he's great, but I see there's definitely holes in there," Weidman said on an episode of Submission Radio in late September. "... That's the goal, to get in there with him."

Weidman's supreme confidence can likely be attributed to two things.

First and foremost, he possesses the kind of unshakable self-belief all great fighters do. Secondly, he's recently seen several other long-term middleweights move up to light heavyweight and achieve major success. 

Anthony Smith has arguably enjoyed the best results of all. While the man nicknamed Lionheart looked gun-shy and, frankly, underwhelming in his March title fight with Jones, he's picked up stoppage victories over top light heavyweight talents Rashad Evans, Mauricio "Shogun" Rua, Volkan Oezdemir and Alexander Gustafsson, all of whom are former champs or title challengers.  

Thiago Santos, who holds a middleweight victory over Smith, has also had success at light heavyweight.

After jaw-jacking knockout wins over top-flight foes such as Jimi Manuwa and Jan Blachowicz, he earned a title shot opposite Jones. Despite entering the matchup as a huge underdog, he battled to a razor-thin split-decision loss. Some onlookers actually scored the fight in the Brazilian's favor, and debates surrounding the result rage to this day.

Think about that. A man who was knocked senseless by David Branch at middleweight gave the greatest light heavyweight ever his toughest challenge to date.

Based on that history, it's easy to understand why Weidman, a former middleweight champion with multiple title defenses on his resume, feels so confident as his debut in the light heavyweight division looms. But is he likely to follow in the footsteps of Smith and Santos? 

While it's possible Weidman backs up his confidence and goes on to challenge Jones, the extreme opposite is also on the table. Against heavier foes with just as much drive to win and markedly more power, the potential for disaster is huge.

Proof is readily available. Just look at Luke Rockhold.

Like Weidman, Rockhold is a former middleweight champion. Like Weidman, he was stopped by strikes in many of his final middleweight bouts. Like Weidman, he probably had more all-around skill than his first light heavyweight opponent, Jan Blachowicz. Like Weidman, he boldly proclaimed himself the harbinger of Jones' demise before he'd even debuted at light heavyweight.

Then he was brutally knocked out by Blachowicz. He was defeated so emphatically that many now believe he should retire.

That's the problem with late-career division changes. While they can sometimes be revivifying, they can also serve as the final nail in a struggling fighter's coffin. This was true for Rockhold. What he viewed as a fresh start looked to his numerous skeptics like a last-ditch effort to get back on track. When it failed, they lowered his career into the ground and buried it. 

Weidman could find himself in a similar situation if he loses to Reyes in Boston—particularly by stoppage, which is a real possibility.

Like Blachowicz, who so effortlessly crushed Rockhold's light heavyweight dreams, Reyes is a top-10 fighter in his division. He's also as venomous a finisher as you'll find in MMA. His last fight, an insipid split-decision defeat of Oezdemir, makes it easy to forget, but he's finished eight of his 11 wins.

Weidman certainly has the skills to defeat Reyes—and potentially even work his way to Jones—but there is no arguing he's got his hands full in his light heavyweight debut. 

In the main event of UFC on ESPN 6, the former middleweight champion will come to a crossroads. One path will lead to a new start in a division other former middleweights have done well in. The other will lead to a grim juncture at which he's viewed as the sport's latest wash-up.

We'll see which one he wanders down.