MMA
Jack Della Maddalena Reveals His Top 6 Madison Square Garden Moments Ahead of UFC 322 Showdown
We are just a week out from UFC 322, where Islam Makhachev steps into the heat to chase history against Jack Della Maddalena for the welterweight crown. Before making his record-setting fourth lightweight title defense at UFC 311, the Dagestani vowed he wouldn’t retire until he became a two-division champion, a climb even his mentor Khabib Nurmagomedov never attempted.
Now, with his lightweight reign behind him, the Dagestani stands on the edge of a career-defining leap. And with the UFC’s yearly return to Madison Square Garden, the stakes feel even bigger. MSG is called the world’s most famous arena for a reason. The only question is whether this mega main event can join the venue’s all-time great moments. The reigning 170-pound champion seems to think so, as he recently ranked the most iconic nights ever held at the Garden.
The Fight of the Century: Ali vs. Frazier I at MSG
Jack Della Maddalena’s pick- #2
On 8 March 1971, the world hit pause as Madison Square Garden hosted ‘The Fight of the Century,’ a showdown between two undefeated heavyweight kings: Muhammad Ali and Joe Frazier. Ali, returning from exile after refusing the draft, stepped back into the spotlight against the relentless reigning champion.
This wasn’t just a boxing match. It was a cultural earthquake. Ali embodied the anti-establishment movement, while Frazier was embraced by the pro-Vietnam crowd. Inside the ring, Ali’s speed and crisp jab collided with Frazier’s constant pressure and brutal left hook.
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Round after round, ‘Smokin’ Joe’ dug to the body and marched forward. The defining moment came in the 15th, when Frazier unleashed a picture-perfect left hook that sent Ali crashing to the canvas. Frazier won by unanimous decision, handing Ali his first professional loss and sealing his place as the undisputed heavyweight champion of the world.
Happy Birthday, Mr. President: Marilyn Monroe at MSG
Jack Della Maddalena’s pick- #6
On 19 May 1962, Marilyn Monroe turned a simple birthday greeting into one of the most unforgettable moments in American pop culture. The stage was Madison Square Garden, packed with 15,000 guests for a Democratic fundraiser honoring President John F. Kennedy’s 45th birthday.
Monroe arrived fashionably late, after being introduced several times, which only pushed the anticipation higher. When she finally stepped out, she slipped off her white ermine coat to reveal a skin-tight, flesh-colored gown sparkling with thousands of rhinestones, so form-fitting it had been sewn onto her.
Under a lone spotlight, she delivered her breathy, intimate “Happy Birthday, Mr. President,” followed by a playful twist on “Thanks for the Memory.” The performance instantly set off whispers, adding fuel to long-rumored ties between Monroe and Kennedy.
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The President even joked afterward that he could retire from politics after having the song sung so wholesomely. Tragically, this would be one of Monroe’s final public appearances, as she died less than three months later, while Kennedy was assassinated in 1963.
Conor McGregor Becomes the First Champ-Champ at MSG
Jack Della Maddalena’s pick- #4
On 12 November 2016, Conor McGregor carved his name into combat sports history at Madison Square Garden, headlining the UFC’s long-awaited New York debut. Already the reigning 145lbs kingpin, McGregor entered the cage with one mission: to become the first fighter to hold two UFC belts at the same time.
And against a veteran like Eddie Alvarez, the Irishman delivered one of the cleanest striking performances the sport has ever seen. He controlled distance with ease, repeatedly punishing Alvarez with laser-accurate left hands, dropping him three times in the opening round.
The finish arrived in Round 2, when McGregor unleashed a crisp four-punch combo capped by another crushing left that sealed the TKO at 3:04. In an image that instantly became iconic, McGregor slung both belts over his shoulders and declared, “I’d like to take this opportunity to apologize… to absolutely nobody!”
The event shattered MSG’s gate record with a massive $17.7 million, solidifying ‘The Notorious’ as the premier showman and biggest draw in UFC history.
Michael Jordan’s Legendary “Double Nickel” at MSG
Jack Della Maddalena’s pick- #3
On 28 March 1995, just five games into his comeback from baseball, Michael Jordan delivered a performance at Madison Square Garden that reminded the world exactly who he was. Wearing the number 45, Jordan torched the New York Knicks for 55 points in a game that instantly earned the nickname ‘The Double Nickel.’
His scoring barrage was vintage Jordan. He dropped 35 in the first half alone, slicing through one of the league’s toughest defenses and setting the Garden buzzing as only he could. Every jumper, fadeaway, and drive felt like a message: the king had returned.
But the defining moment wasn’t a shot. With the score tied and the Knicks swarming him on the final play, Jordan drew the defense, then slipped a perfect pass to Bill Wennington for the go-ahead dunk with 3.1 seconds left.
Chicago won the match with 113-111. However, that night proved Jordan wasn’t just back as a scorer. He was back as the game’s ultimate closer.
John Lennon’s Final Major Performance
Jack Della Maddalena’s pick- #5
On Thanksgiving night, 28 November 1974, Madison Square Garden witnessed a moment that would become rock-and-roll lore. John Lennon made his final major concert appearance, stepping on stage as a surprise guest with Elton John.
The cameo came from a friendly wager: Elton bet Lennon that their collaboration, Whatever Gets You Thru the Night, would hit number one. Lennon didn’t believe it. When the song topped the charts, he owed Elton one performance. And he paid up.
A visibly nervous Lennon walked out to a thunderous welcome and joined Elton’s band for three songs: their chart-topping duet, a soaring version of Lucy in the Sky With Diamonds, and a joyful performance of I Saw Her Standing There. Before the last song, Lennon joked that it was written by an old estranged fiancé of mine named Paul.
The night carried an even deeper meaning. Yoko Ono was in the crowd, and the two reunited backstage after the show. The performance became a warm, bittersweet landmark in pop culture history, remembered not only for its musical magic but because it turned out to be Lennon’s final major public appearance before his death six years later.
Islam Makhachev vs. Jack Della Maddalena: UFC 322
Jack Della Maddalena’s pick- #1
Madison Square Garden is set for a true mega-fight on 15 November 2025, as welterweight king Jack Della Maddalena puts his crown on the line against former lightweight champion Islam Makhachev. After vacating his 155-pound belt to chase two-division glory, Makhachev has turned UFC 322 into one of the most anticipated cards of the year.
May 11, 2025, Montreal, Qc, Canada: Co-main event Men s Welterweight Bout: BELAL MUHAMMAD vs JACK DELLA MADDALENA in UFC 315 at Bell center in Montreal, QC, Canada on 2025-05-11 Montreal Canada – ZUMAl189 20250511_zsp_l189_001 Copyright: xYannickxLegarex
The matchup is a classic clash of styles. The Aussie brings laser-sharp boxing, fight-ending power, and timing that can flip a bout in seconds. Standing across from him is Makhachev, the relentless grappler whose pressure and top control have suffocated almost everyone at lightweight.
Feeling the magnitude of the moment, the Australian champion even ranked this showdown as his personal #1 pick among the most iconic events ever to hit MSG.
