Jimmy Floyd Hasselbaink explains choosing Middlesbrough over AC Milan in 2004
Last Updated: 03/01/19 7:19am
Former Leeds United and Chelsea star Jimmy Floyd Hasselbaink has revealed why he chose to join Middlesbrough over AC Milan in the summer of 2004.
The Dutch forward, who was 32 at the time, was a free agent after being told by Chelsea he was surplus to requirements following the hiring of Jose Mourinho, who signed Didier Drogba and Mateja Kezman to be his strikers.
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Among his suitors were reigning Serie A champions AC Milan, who were managed by Carlo Ancelotti and boasted a star-studded squad that contained players like Paolo Maldini, Alessandro Nesta, Andrea Pirlo, Kaka and Andriy Shevchenko.
But Hasselbaink was far from swayed by the Rossoneri's star power and admitted he was not enamoured by the prospect of backing up Ukrainian superstar Shevchenko, who had just won the Ballon d'Or.
When asked who came in for him after he left Chelsea, Hasselbaink told the Transfer Talk podcast: "Besiktas and AC Milan, but I wanted to stay in England.
"If I would have gone to AC Milan, Shevchenko was there at the time. They always played with one striker. They said as well 'you are going to be behind Shevchenko'. They had the Danish striker there as well, [Jon Dahl] Tomasson.
"I wanted to play football. I was 32. I wanted to play week in, week out.
"They were not like 'oh we want you, you are going to be the number one'. They were more like 'you are going to be the backup for Shevchenko'. I did not want that."
Hasselbaink instead headed north to the Riverside Stadium to play under future England coach Steve McClaren.
He was one of four big-name signings, along with Michael Reiziger, Ray Parlour and Boudewijn "Bolo" Zenden, who joined on free transfers, while Mark Viduka arrived from Leeds United in a £4.5m deal.
Recalling his decision to choose Boro, Hasselbaink explained: "I was on holiday and I got a call from George Boateng, who I know from the Dutch national team.
"He called me and said 'would you fancy coming to us?' He was calling for Steve McClaren.
"He then started talking about Middlesbrough and the players and how it was. He told me 'you should come, you would really enjoy it'.
"When I spoke to Steve McClaren, he said he wanted to bring in two strikers and play two strikers up front - me and Mark Viduka.
"Obviously, Viduka had a Leeds background as well. I always liked Viduka as a player and I could see that working.
"And it did work. That year, we got the best position in the Premiership in Middlesbrough's history (seventh). We went into Europe as well and the year after, we got to the final of the UEFA Cup with a crazy cup run that I will never, ever forget. It was amazing.
"We had a great time with a really nice team - [Gaizka] Mendieta, [Boudewijn] Zenden, Ugo Ehiogu, Gareth Southgate, and [Mark] Schwarzer.
"We had a hell of a team and it was a really good time."
Jimmy Floyd Hasselbaink was speaking exclusively to the Sky Sports News Transfer Talk podcast. The full episode will be available from 6am on Sunday, and you can watch it On Demand on Sky Sports, on YouTube, or listen to it on your preferred podcast provider.