Massimo Taibi (1999)

A man every Red Devils fan was glad to see the back of. Sir Alex was faced with a dilemma when heir-apparent to Peter Schmeichel’s goalkeeping throne at the Theatre of Dreams, Mark Bosnich was stricken with injury which left Raimond van der Gouw between the sticks. Taibi, formerly of AC Milan, was purchased for 4.5 million as a solid Italian goalkeeper seemed a safe choice for Ferguson. Massimo proceeded to flap at a Liverpool corner resulting in a Sami Hyypia goal in his debut at Anfield in which he was rather thrown in at the deep end.

However, the second half meant the tables had turned which allowed Taibi to shine, producing a string of saves, including thwarting Vladimir Smicer from a one-on-one situation as the Italian went onto a man of the match performance. Fergie believed that he had struck gold. We had been warned with that one mistake at Anfield but two games that Taibi and the United faithful will want to forget came within days of each other.

Taibi got through the 1-1 draw at home to Wimbledon unscathed in terms of his reputation but in the next home game the following week against Southampton, a certain Mr. Le Tissier would make Taibi live long in the memories of United fans, albeit negatively. A tame 30-yard effort looked as though Taibi would swallow the ball with ease, that he did. He swallowed the ball, then it proceeded to squirm under his body, through his legs to slope slowly but surely into the net.

That particular gaffe resulted in a 3-3 draw at home to Southampton, a week before Taibi decided to inexplicably punch Gary Neville accidentally resulting in the first goal of a 5-0 rout at Stamford Bridge which was United’s first league loss in ten whole months since a 3-2 loss to Middlesbrough in December 1998. Five goals went in and Taibi’s three-week United stint as goalkeeper generated four appearances and carnage befell Manchester.

Roy Carroll (2001-2005)

After the flops of a certain goalkeeper in the list and a World Cup winning Fabien Barthez, Roy Carroll was seen as a step down as Ferguson was reeling through potential goalkeepers in order to finally find Peter Schmeichel’s successor that was found in the purchase of Edwin van der Sar which swung the door open for Northern Irish, Carroll to exit the club.

In the mid-2000’s, United were going through a transitional period, a period which saw the legends of Schmeichel, Irwin, Stam, Beckham, Keane, Butt, Yorke and Cole from the Treble winning side leave, to be replaced by Kleberson, Blanc, Djemba-Djemba, Forlan and Veron. Carroll was a by-product of this transitional period. Carroll was producing the goods in what was to become an undefeatable Arsenal season but soon after ghost goal at home to Tottenham in which he clearly blundered in Pedro Mendes’ speculative effort, he was soon gone and traded in for Tim Howard.

Fabien Barthez (2000-2004)

The legacy of a certain Danish goalkeeper left behind the car wrecks of goalkeepers who attempted to follow in the footsteps of the Great Dane, Peter Schmeichel. At the turn of the century, Barthez was coming off the back of a World Cup and European Championship double with France and was seen as the best goalkeeper in the world. In the four-year spell at the club, we saw the best and worst in the Frenchman.

The best came in spectacular saves such as thwarted Dietmar Hamann in the Premier League at Anfield in 2002 along with his penalty saving antics at Fulham but his worse came with what seemed like a battle between him and Wes Brown against Deportivo in the 2001-02 Champions League campaign, a battle which was tied on cock-ups at 1-1 in a match United lost 3-2.

However, the worst from Barthez came in an FA Cup tie at home to West Ham in 2001. The sheer arrogance and stubbornness from the World Cup winner to stand with his hand aloft, attempting to coax both Paolo di Canio and the referee to stop play for an alleged offside before the Italian duly stuck in the winner which eliminated United from the FA Cup.

Juan Sebastian Veron (2001-2003)

For the price tag that was slapped on this Argentine slaphead, he didn’t half fail to produce for Fergie. Long-time United central midfielder Paul Scholes was sacrificed onto the substitutes bench as well as the 4-4-2 formation as it seemed the United side was going to be built around the almost 30 million pound man. He was sold two years on for almost half of the purchase price to oil-rich Chelsea. One thing can be said about Veron, he was a half-decent goalscorer and strikes against Tottenham in that memorable 5-3 win and Bayer Leverkusen in 2002 in my first match at Old Trafford.

Not only was Seba one of Fergie’s worst buys but ranks on many lists of worst Premier League transfers in the entirety of the 20 years it has existed.

Dimitar Berbatov (2008-present)

Here’s to part one of two in bold statements from me towards flops by Sir Alex Ferguson. Yeah, Dimitar Berbatov – the shared holder of the Premier League golden boot for the 2010-11 season (and even then he was a substitute for the main stay of the season.) The Bulgarian striker is dubbed as lazy and poor and recently has had his wish to leave Old Trafford accepted at the end of this season.  Five goals at home to Blackburn and hat-tricks against Liverpool and Birmingham meant three fifths of his league goals came in the space of three games.

Impressive? Ferguson left him out of the Champions League squad as the Bulgarian rarely got a chance to prove himself for the 30 million fee which remains United’s transfer fee record.

Jaap Stam (1998-2001)

The final part of my bold choices for this list is Jaap Stam. In the late 20th century, Stam was arguably the cornerstone in his opening season at United as he helped the Red Devils along the way to a historic treble winning season. A goal in the 6-2 victory at Filbert Street was memorable as well as many crucial tackles and clearances, most notably against the likes of Inter Milan.

Stam’s English dream was short lived as he notched up three titles in as many seasons before letting slip comments in his autobiography which infuriated and subsequently forced Ferguson into selling the Dutch defender. Ferguson has since admitted his mistake but for the price that Stam cost United he should be regarded as a flop, especially seen as though one of the few mistakes in his almost 26-year tenure Ferguson has admitted to was selling this man who could’ve moved onto legendary status at the Theatre of Dreams.

Kleberson (2003-2005)

As I said previously, through Arsenal’s undefeated season and Mourinho’s brief dominance of English football was a transitional period. Another World Cup winning player in Kleberson who triumphed in 2002 with Brazil failed to live up to expectations in Manchester in his frankly poor thirty performances with two goals in his two seasons at United. To add insult to injury, Ferguson lost four million in profit from the sale on to the Turkish club of Besiktas.

Eric Djemba-Djemba (2003-2005)

So good they named him twice? They could’ve named him three times but it still wouldn’t have excluded Eric Djemba-Djemba from this list. His time at United was almost identical to that of Kleberson’s except this Cameroonian midfielder wasn’t a World Cup winner. He was 22 years of age when he embarked on the Community Shield in 2003, tearing into the Arsenal squad in Cardiff. I was privileged to witness his only goal at Old Trafford as he scored the fifth against Panathanaikos where he sent a two-yard screamer into the roof of the net.

He led Kleberson in terms of appearances by only nine in a poor stint for both parties as United made a 2 million loss on him when he was sold to Aston Villa in 2005.

Diego Forlan (2001-2004)

He came from Uruguay, he made the Scousers cry but let’s not forget that it took Diego Forlan until his 27th appearance when he rattled in a late penalty against Maccabi Haifa.  He had to wait a further eight matches for his first goal from open play as he equalised against Aston Villa. Forlan was becoming a cult hero on the terraces of United and the fact that he went onto become a prominent goalscorer for Villarreal, Atletico Madrid and winning the Golden Ball at the 2010 World Cup.

Just like Stam, Ferguson could’ve perhaps kept hold of the Anfield brace-scoring Uruguayan for much longer and he would’ve reaped the rewards. Forlan might have become a cult hero in his final days at Old Trafford but those 26 fruitless matches might have made him a cult legend but not necessarily the best forward at the club – especially behind Ruud van Nistelrooy.

Laurent Blanc (2001-2003)

One of three former World Cup winners on this list which proves how often safe transfers for one of the best managers to have ever lived can still flop. Example number three comes from the same squad which brought you Fabien Barthez and not to mention the likes of Zinedine Zidane, Thierry Henry and the like. The only mistake Ferguson made was not signing Blanc sooner in his career as the French Barthez-kissing defender was 35 years of age upon his signing.

His poor performances and five successive losses against Bolton, Liverpool, Arsenal, Newcastle and Chelsea spell out his surname in his opening season. These weren’t good omens for the player who previously notched up 11 goals for Marseille in a season, Blanc netted four times in two seasons in a career which culminated in a Premier League for which he was sporadically selected.