Terence Crawford is coming off the biggest fight of his career. The Nebraska native defeated Canelo Alvarez via unanimous decision to become not only the new undisputed super middleweight champion but also a three-weight undisputed champion in the four-belt era. The historic win cemented his legacy while opening several new doors for the 38-year-old. Though it remains unclear whether Crawford will continue fighting or embrace retirement, one thing is certain—he won’t be short of challengers.

Meanwhile, his old rival from the welterweight days, Jaron ‘Boots’ Ennis, has officially moved up to the 154-pound division. His debut at the new weight saw him face Uisma Lima, a bout he won in dominant fashion with a first-round knockout. With names like Vergil Ortiz Jr., Bakhram Murtazaliev, Abass Baraou, Sebastian Fundora, and Xander Zayas on the table, Ennis has plenty of intriguing options. Still, the fight fans truly want is a showdown with Terence Crawford. For that to happen, one of them would have to move in weight—and if it does, what exactly would Crawford stand to gain or lose?

Pros of fighting Jaron Ennis for Terence Crawford

The biggest advantage for Terence Crawford in fighting Jaron Ennis would be the massive payday that comes with it. After defeating Canelo Alvarez, Crawford became an overnight global sensation. Canelo was viewed as an almost unbeatable force, until Crawford dismantled him with ease. Now, Crawford’s market value is higher than ever, and a bout against a long-discussed rival like Ennis could easily surpass even his Canelo payday. 

According to reports, Crawford earned around $50 million from that fight. If he steps into the ring with Ennis, he would undoubtedly be the A-side, commanding an equal or even larger purse. Eddie Hearn, Ennis’ promoter, doesn’t seem opposed to the idea. He recently said, “That is a fight for the ages, against Crawford… Look, Terence is only going to fight ‘Boots’ if there’s loads of money on the line… He’s not gonna fight anymore, unless it’s for a lot of money.”

Beyond the money, there’s legacy. Ennis has long been compared to Crawford due to their shared switch-hitting style, leading fans to label the young star as Crawford’s natural successor. Though a fight between them never materialized when they were both at welterweight, it could now be billed as a ‘mentor versus protégé’ showdown. A win would not only reaffirm Crawford’s dominance across multiple weight classes but also showcase that, even at 38, he can outclass the new generation. 

Defeating a younger, hungry Ennis would break the age barrier and further cement Crawford’s legacy as one of boxing’s all-time greats. However, fighting Ennis comes with its disadvantages as well. 

Cons for Terence Crawford against Boots Ennis

Even though Terence Crawford completely outclassed Canelo Alvarez, dropping back down in weight to face ‘Boots’ Ennis could prove to be a major challenge. Cutting weight at 38 would not only be physically taxing but could also leave Crawford vulnerable against a much younger, faster opponent. Ennis, who is a stylistic match and nearly a decade younger, possesses quick footwork and a high punch volume.

These tools could trouble even the most seasoned fighter. Moreover, Crawford’s bout against Israil Madrimov last year revealed that he isn’t entirely without weaknesses. Ennis could train and adapt to exploit those weaknesses to overcome Crawford. A loss to Ennis could be devastating for Crawford’s recently solidified reputation as the pound-for-pound best across eras and divisions. 

After his dominant performance against Canelo, Crawford would enter the Ennis fight under immense pressure from both the media and fans to dominate once again, especially against a less experienced Ennis. Anything short of a one-sided victory could tarnish his legacy and shake his image as boxing’s ultimate standard-bearer. Not to forget, fighting Ennis could also delay any potential plans for a rematch with Canelo Alvarez.

A Canelo Alvarez rematch would be much more lucrative, giving Crawford the chance to demand a 50-50 purse split, which can be in the hundreds of millions. Additionally, Crawford doesn’t need to go down in weight; he has already won a belt in the division. The only way a fight against Ennis would make sense is if the Philadelphia native becomes the undisputed champion in his division and Crawford fights him to become the first four-weight undisputed champion. 

But that isn’t happening anytime soon. 

At the end of the day, weighing the pros and cons, it might be wiser for Terence Crawford to wait for a potential rematch with Canelo Alvarez, if that opportunity arises. Alternatively, he should retire at the pinnacle of the sport as the undisputed pound-for-pound king. He has already achieved what few fighters in history ever have. But what do you think? Should Crawford, at 38 years old, return for one last mega payday against Jaron Ennis, or walk away with his legacy untouched?