Dempsey's deadline-day move took him to the former club of his national team boss, Tottenham, where Klinsmann had two separate stints.
Count Klinsmann a fan of the transfer which took the Texan midfielder across London from Fulham, where Dempsey spent over five years.
"We are happy that this whole thing was finalized, that he got the move to a real international club that is always competing in the top four or six of the Premier League," Klinsmann said. "I personally, I'm excited because I played for Tottenham many, many years ago. It gives me me a chance to watch one of his games in one of my old places."
Klinsmann had a habit of hopping around in his playing career. After leaving his hometown of Stuttgart, he hardly stayed in any one country longer than a couple of years, let alone at one club. The polyglot crisscrossed Europe, picking up languages, cultural experiences and goals. So the 48-year-old German understands some of the bad blood that comes with leaving a club.
Dempsey's move was particularly protracted. The 29-year-old refused to sign a contract extension and was fined two weeks' wages when he sat out a preseason trip. Fulham officially reported Liverpool FC for its public and aggressive attempts to woo Dempsey. Eventually, minutes before the transfer window closed in England, Tottenham swooped in and nabbed the scorer of 17 Premier League goals last season.
"It is really important now that Clint can put this behind him. It was not all the time really pretty what happened the last couple weeks there," Klinsmann said. "Obviously he dragged that with him over the whole summer. Already coming into our May/June camp [it] was always in the back of his mind. He was concerned about it, which is normal."
Klinsmann called Dempsey into the 24-man roster which will face Jamaica twice in four days in World Cup qualifying. The first match is on Sept. 7 in Kingston, Jamaica. With Dempsey excluded from Fulham's first two Premier League matches this season, his fitness levels are still a question mark.
"We'll evaluate him. We'll sit down with him," Klinsmann said. "We'll discuss his state of mind and also obviously we'll test his fitness level right away when he comes in to see where he's at in order to help him. If he's lagging behind then we'll know exactly where he's at and we can help him to catch up as quickly as possible."
With Landon Donovan and Michael Bradley missing out through injury, Dempsey's role becomes more essential for the Stars and Stripes. Klinsmann may even start him, sans recent match action, saying, "We're absolutely open to throw him in the water right away."
"It really depends on where he's at, if he's in a very good physical level," Klinsmann said. "He worked out with the fitness coach of Fulham on the side. They did one-on-one work, which is often more effective than team training."
Another crucial American player to secure a transfer on the last day of the window was U.S. captain Carlos Bocanegra. The 33-year-old jumped from Rangers, where he had played a few matches in the Scottish fourth division, to Racing Santander.
"At least he played a couple of games," Klinsmann chuckled. "He's a little bit more in a match rhythm. We're pleased for him that he made that move and plays in a very competitive Spanish second division in there, which is awesome for him."
The former Inter and Bayern Munich striker indicated that Bocanegra will undergo similar fitness tests and any lineup decisions would be based on his physical state.
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