The fight with Jack Della Maddalena could be the biggest mistake of Islam Makhachev’s career – and here’s why.

Islam Makhachev, the reigning king of UFC dominance at lightweight, has never shied away from a challenge. But in stepping up to face Jack Della Maddalena at welterweight, the Russian superstar might be making a career-defining gamble—and not in his favor.

While most fans see the move as a bold step toward two-division greatness, others argue that this particular matchup could backfire spectacularly. In fact, there’s growing concern that the fight with Jack Della Maddalena (JDM) could become the biggest mistake of Makhachev’s career.

Let’s break down why this seemingly exciting opportunity could spiral into a high-stakes disaster.

Jack Della Maddalena: A Rising Monster in the Welterweight Division

If you’re not already familiar with Jack Della Maddalena, you should be. The 27-year-old Australian phenom has surged through the UFC ranks with precision boxing, surgical aggression, and a knack for brutal finishes. His blend of volume, power, and pressure has left opponents gasping for air—both figuratively and literally.

While Makhachev has dominated wrestlers and elite grapplers at lightweight, JDM presents a new kind of nightmare: an elite striker with size, reach, and relentless forward pressure.

And worst of all? He has nothing to lose.

For Makhachev, a loss would tarnish his legacy. For Della Maddalena, a win would turn him into a global star. That imbalance in pressure could be fatal for the Dagestani star.

Islam Makhachev: The Lightweight King in Unfamiliar Territory

Makhachev’s dominance at 155 pounds is undisputed. He’s defeated the likes of Charles Oliveira, Alexander Volkanovski, and Dustin Poirier (among others) with clinical control and suffocating wrestling. But the leap to 170 pounds comes with significant risk.

At lightweight, Makhachev is strong, explosive, and physically overwhelming. At welterweight, however, he will no longer be the bigger man. Fighters like JDM, Shavkat Rakhmonov, and Kamaru Usman naturally walk around at 190+ pounds. Makhachev, by contrast, is a lean 175 at most.

That size difference could negate his greatest weapons—his control and positional dominance.

Grappling vs. Volume: Will Makhachev’s Control Be Enough?

The biggest question heading into the fight is whether Makhachev’s grappling can neutralize JDM’s striking blitz.

But unlike Charles Oliveira—who welcomed grappling exchanges—Jack Della Maddalena won’t give Islam any free entries. His takedown defense has improved drastically, and his ability to scramble back to his feet has turned into a weapon of its own.

If Makhachev can’t hold JDM down, he’s going to have to stand with him—and that’s where the real danger lies. JDM lands nearly 6.5 significant strikes per minute. Makhachev? Only around 2.3.

And while Makhachev’s striking has improved, it’s nowhere near the level of Jack’s fluid, technical boxing.

One Clean Shot Could End It All

We’ve seen Makhachev dropped before—by Adriano Martins and nearly by Volkanovski. But he always recovered thanks to quick grappling reactions. Against a true welterweight with knockout power, those few seconds of vulnerability could be lethal.

Della Maddalena doesn’t just hurt people—he finishes them. 14 of his 17 wins are by knockout. And he has shown the ability to generate power in close range, mid-range, and even off his back foot.

One clean left hook, and Islam’s dreams of being a two-division champion could go up in smoke.

Islam’s Legacy Is on the Line

This is not just another fight—it’s a legacy gamble.

Makhachev could have stayed at lightweight, defended his title again, and gone down as the greatest lightweight of all time. Instead, he vacated his belt, stepped into unfamiliar waters, and accepted a challenge that could destroy everything he’s built.

If he loses to Jack Della Maddalena, critics will ask:

• Why did he leave his weight class?

• Why not wait for a bigger-name welterweight?

• Did he underestimate Jack’s threat?

A single bad night could eclipse a decade of dominance.

The Retirement Clock Is Ticking

Adding more urgency to the matter is Makhachev’s reported retirement timeline.

According to his coach Javier Mendez, Islam likely has only three fights left in his career. If this is true, then every fight from now on is a precious opportunity to cement his legacy—or shatter it.

Spending one of those final fights on a high-risk, low-reward opponent like JDM may not be the smartest strategic move. There are safer ways to chase history.

A rematch with Ilia Topuria, a superfight with Leon Edwards, or even a farewell bout in Dagestan would be easier to market and less dangerous.

The UFC Isn’t Helping His Case

Let’s be honest: Jack Della Maddalena doesn’t have mainstream star power yet. He’s a fan-favorite among hardcore fans, but to casual audiences, his name lacks buzz.

That means if Makhachev wins, he doesn’t get the boost a fight with Leon Edwards or Colby Covington would give him. But if he loses, he gives Jack his breakout moment while taking a permanent dent to his own career.

In business terms, it’s a lose-lose scenario for Makhachev.

Stylistic Nightmare: The Aussie’s Chaos vs. Dagestan’s Discipline

Makhachev’s strength lies in order—grabbing control, dictating pace, and grinding opponents into submission.

Jack’s strength lies in chaos—swarming attacks, unpredictable combinations, and mid-fight adjustments. He’s comfortable being uncomfortable, and that unpredictability could break Makhachev’s rhythm in a way few fighters ever have.

And if the fight goes into deep waters, JDM’s gas tank and aggression could overwhelm a wrestler who’s struggling with size disadvantage.

Makhachev’s Mindset: Confidence or Arrogance?

Another dangerous variable is Islam’s own confidence.

He’s earned the right to believe in his skills—but is he underestimating Jack? Has dominating at lightweight lulled him into believing he can control everyone, regardless of size?

Many great fighters have fallen victim to this mindset. Just ask Anderson Silva vs. Chris Weidman, BJ Penn at welterweight, or even Max Holloway’s failed move to lightweight.

What Happens If Makhachev Loses?

If Makhachev suffers a knockout loss or even a clear decision defeat, the fallout will be massive:

• His aura of invincibility will vanish.

• Future fights (like a third belt at middleweight) will lose steam.

• His GOAT claims will be seriously questioned.

• Fans will always wonder: Was he just a weight bully at 155?

Even if he comes back and beats Ilia Topuria afterward, the damage may be irreversible.

The Safer Path Was Clear… And He Ignored It

Makhachev could’ve waited for:

• Leon Edwards (the established champ)

• Colby Covington (a name, if nothing else)

• Or even a Nate Diaz superfight

All of these options would have less danger and more financial upside. But instead, he’s chosen the road less traveled—and it may lead him to ruin.

Conclusion: Makhachev’s Most Dangerous Gamble Yet

Islam Makhachev’s decision to fight Jack Della Maddalena may look like a champion chasing greatness, but in reality, it could become the biggest mistake of his legendary career.

He’s stepping into a bigger man’s world, against a savage striker in his prime, with little public reward and all the risk in the world.

If he wins, he survives and advances. But if he loses?

Everything he’s built could crumble in a matter of minutes.