The Borussia Dortmund coach says the Japan international is one of the best in the world, but it brings him to tears to see the midfielder playing a bit-part role at Old Trafford
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But Kagawa was restricted to just 17 starts in the Premier League this season, and Klopp says it is heart-breaking to see such a good midfielder played out of position.
"It could not be our way to do things like Real and Bayern and not think about taxes - and let the next generation pick up our problems," Klopp told The Guardian.
"We need to work seriously and sensibly. We have this amount of money so we can pay that amount. But we lose players. Last year it was Shinji Kagawa.
"Shinji Kagawa is one of the best players in the world and now he plays 20 minutes at Manchester United - on the left wing! My heart breaks. Really, I have tears in my eyes.
"Central midfield is Shinji's best role. He's an offensive midfielder with one of the best noses for goal I ever saw.
"But for most Japanese people it means more to play for Man Utd than Dortmund. We cried for 20 minutes, in each others' arms, when he left."