After sitting out most of the summer as he awaited a move out of Fulham, it appears likely that Dempsey will see playing time with the U.S. team in Jamaica.
Following a drama-filled summer with Fulham that ended with Dempsey sitting out the first two games of the Premier League season before moving to Tottenham at the transfer deadline, the star midfielder's fitness was put into question ahead of the World Cup qualifying match in the Caribbean.
But after spending a few days with the national team in Miami prior to arriving in Kingston on Thursday morning, Klinsmann hinted that his best player could be ready to start against the Reggae Boyz.
"He looks good and he looked sharp in training," Klinsmann said. "Overall the last three or four days went really well in Miami for us. We have all the guys at our disposal and we are eager to prove a point tomorrow night."
The U.S. is already missing midfielders Michael Bradley and Landon Donovan due to injury and defender Maurice Edu hasn't been playing on a club level as he has also been in transfer limbo. Not having Dempsey would have been a major blow as the team looks to earn a spot in Brazil in 2014.
Klinsmann says it's his job as the national team coach to get his players ready for international matches in short notice and he feels the team is "looking pretty good" at the moment.
"We have to pick them up wherever they left off, that's our job as national team coach," Klinsmann said. "And then we have to evaluate them in a couple of days now and see where they're at. I think that we are looking pretty good."
The U.S. and Jamaica kick off at 8 p.m. ET on Friday and will match up again four days later in Columbus, Ohio.