Massimo Maccarone spent 5 years at Middlesbrough, alternating a few good season with some disappointing ones

On Her Majesty’s Service: The Rise and Fall of Massimo Maccarone

A name that rings true with Middlesbrough fans, Massimo Maccarone was an eccentric addition to the long list of fine Boro strikers. From Fabrizio Ravanelli to Mark Viduka, to Jimmy Floyd Hasselbaink, Yakubu, and Maccarone – the Riverside has long been the home of some great forwards, and the latter proved many wrong with his performances for the club.

By no means was he on par with the likes of Viduka or Hasselbaink, but Maccarone’s time in England is both memorable, and frustrating for fans. Memorable for some important goals in Europa and the Premier League, frustrating because of the hefty price-tag paid, and the seemingly contested attitude of the Italian.

The Carrara-born Maccarone started his career with Milan. He never made a first-team appearance for the club but made his name in his homeland with the likes of Prato and Empoli. With Empoli, Maccarone scored 30 goals in two seasons and announced himself as one of the Azzurri’s best young strikers, making his first and only two appearances for the national team in 2002.

Maccarone made his senior debut with Italy in a March 2020 friendly game against England. At that time, he was considered one of the most promising strikers among his fellow countrymen...
Maccarone made his senior debut with Italy in a March 2002 friendly game against England. At that time, he was considered one of the most promising Italian strikers of his generation…

He’d scored 10 goals in the 2001-02 Serie B season and 11 in 15 for the Italian U-21 side, who reached the Semi-Finals of the 2002 UEFA European U-21 Championship that season. Many clubs were lining up to take Maccarone from Empoli, but he opted for the North East of England and became Boro’s record signing at the time, joining for little over £11 million.

That sort of money was a lot for the time, and a lot for Steve McClaren’s Middlesbrough who were starting to establish themselves as a regular Premier League team – they’d just finished 12th in the league after three similar finishes prior. The arrival of Maccarone and the money spent was meant to assert Boro in the “next level,” as they looked to become a top-half Premier League side.

Maccarone did well to emulate his Serie B record at Empoli with then Premier League side Boro – he scored 9 goals in 34 Premier League games in his first season at the club, highlights of which include scoring on his home debut and bagging a brace in a 5-1 win over Tottenham Hotspur.

Having turned 23-years-old during his first season at Boro, Maccarone’s debut campaign in England announced him as one of the hottest young strikers in the continent, let alone England. Nobody expected him to hit the ground running like he did and it made McClaren and co. look like geniuses. Though the early hype was just that – Maccarone wouldn’t enjoy a campaign half as successful as his first in the next four seasons with Boro.

Massimo Maccarone had a shimmering start in his Premier League debut season, bagging a home brace against Fulham to introduce himself to the British football lovers
Massimo Maccarone had a shimmering start in his Premier League maiden season, scoring in his home debut against Fulham to introduce himself to the British football lovers

McClaren’s Middlesbrough was an exotic side with players from all over the world. It was an iconic time in the club’s history and along with the likes of Maccarone, there was Juninho, Doriva, Gaizka Mendieta, Slizard Nemeth, and a young Stewart Downing breaking through. The competition was rife at the Riverside and in the 2003-04 season – Maccarone’s second at the club – he’d make 22 Premier League appearances, scoring 8 in all competitions.

Next summer’s signings of Jimmy Floyd Hasselbaink from Chelsea and Mark Viduka from Leeds all but confirmed the premature end of Maccarone’s Middlesbrough career, and he would spend the entirety of the 2004/05 season on loan at Parma, and then Siena. In the second half of the season with Siena he managed eight goals and put himself back in contention for his return to England though, and he’d prove to be an unlikely hero for his side that season.

With 2 goals in 17 Premier League appearances, Maccarone didn’t provide domestically, but continentally, he would fire Middlesbrough all the way to the final of the 2006 UEFA Cup. His first two of five European goals that season came in the 2-0 win over Litex Lovech which sent Boro through as group winners. McClaren’s side would overcome Stuttgart and Roma to arrange a Quarter-Final clash with Basel, and the Swiss would win the first-leg 2-0. Back at the Riverside, it was Maccarone’s 90th-minute goal that capped a 4-1 win and sent Middlesbrough into the Semi-Finals of the UEFA Cup.

They faced an unlikely Steaua Bucuresti in the Semi-Finals and again Middlesbrough lost 0-1 the first-leg. The Romanian’s took an unstable goal lead to the Riverside and registered two more, leaving Boro with four to find – which came from Maccarone, Viduka, Chris Riggott, and again, in the 89th-minute, Maccarone.

Although the Final was lost 4-0 to Sevilla, Middlesbrough went out as proud runners-up, giving fans a journey like no other they’ve experienced before and if it weren’t for two late goals from a certain Maccarone en route, none of it would’ve been possible.

With this last-minute diving header, Massimo Maccarone gave Middlesbrough fans one of the most exciting moments in their history, wrapping an astonishing comeback to push Boro into an unprecedented UEFA Cup Final
With this last-minute diving header, Massimo Maccarone gave Middlesbrough fans one of the most exciting moments in their history, wrapping an astonishing comeback to push Boro into an unprecedented UEFA Cup Semi-Final

However, the following 2006-07 season would prove to be Maccarone’s last – he managed just eight games and a goal before he was off-loaded midway through the season. He rejoined Siena on a free transfer in February 2007 and would enjoy a successful career spell, scoring 48 in 131 games over the next three years. That was followed by fleeting spells at Palermo and Sampdoria, before Maccarone signed again for Serie B side Empoli in January 2012.

In five-and-a-half seasons he would help Empoli into Serie A, scoring 71 goals along the way and reminding everyone of how good a goal scorer he really was. Now aged 40, Maccarone is retired and lying low, finishing off his career with a stint in Australia, before a final hurrah in 2017 with Serie C, and hometown side, Carrarese.

Maccarone tainted his Middlesbrough stay after leaving. He called out McClaren for his inept treatment of him and fell into a back-forth with then-chairman Steve Gibson, who labeled the Italian a fool. Perhaps he was a bit foolish, in the same sense that his Italian counterpart Paolo Di Canio might have been. But like him, isn’t that controversy combined with sheer talent what made Maccarone so great? He’s over 220 career goals and whilst English fans didn’t see the entire story, he was regarded as a naturally gifted finisher before and after his time at the club.

He was an extrovert and an eccentric, and never too afraid to express himself both on and off the pitch. Maccarone’s time at Middlesbrough was fruitful but ultimately underwhelming, struggling with the world-class competition at the club during a successful time in their history. But he was certainly a part of that success and despite what’s been said and done by whoever, fans should remember him for the gifted footballer he was.

Click below to read more stories of Italian players who tried their hand at the Premier League:

Gianfranco Zola’s Inspiring Love Affair with Chelsea
Roberto Di Matteo’s Managerial Greatness
Benito Carbone’s British Tribulations
The Turbulent Times of Paolo Di Canio
Alberto Aquilani’s Missed Chance at Liverpool
Everton Full-Back Alessandro Pistone and His Injury Hell
The Hard-Hitting Times of Gianluca Festa at Middlesbrough
Attilio Lombardo’s Short Stint at Crystal Palace
Carlo Cudicini Could Have Been a Top Star

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