After all, the U.S. international has been an English Premier League player for six years—and a top-tier one for two of those—so why was his move to White Hart Lane accompanied by such a bad hangover?
Although not everyone has noticed, Dempsey has started to turn a corner.
Eighty minutes on the pitch against Panathinaikos served as another important step toward his redemption, so let's analyse the change in his game that's allowed him to come to form.
Dempsey has been used in a variety of positions by Andre Villas-Boas this season, just like he was by Martin Jol last season.
No matter what starting position he has featured in, however, the key for his resurgence in form is his ability to move into the area highlighted on the diagram.
Against Panathinaikos, Dempsey operated from the left but spent almost no time widening the pitch by staying touchline wide. He received 40 passes, but more than half of them were infield.
This meant he was operating between the two banks of four that Panathinaikos had set up by ghosting inward from wide left. The right-back couldn't follow him, and the central midfielders couldn't close the gap in time.
Once he's in that position, he's looking for the killer baller. He's playing as a traditional No. 10 whenever he can and benefits from the fact that Jermain Defoe hangs on the defender's shoulder as well as anyone in the game.
Pass completion percentages be damned—Dempsey tried at least six through-balls against the Greek side. A few were cut out easily, but one was an assist for Emmanuel Adebayor's opener.
He didn't start well because he wasn't playing in the right areas or playing to his own strengths. Andre Villas-Boas shouldn't be blamed for this—in fact, he could be commended for pulling the plug on a failing experiment and reinstating the American to the position he has become most comfortable with.
The difference is remarkable. It seems that high risk, high reward works wonders for the former Fulham player, and he managed perhaps his best-ever performance in a Tottenham shirt against his former club.
Get him in the right areas, ask him to thread those balls and they will come off. If he doesn't take a central creative role in the team, he doesn't do a lot else.
Dempsey could well end the season with a 75 percent pass-completion rate accompanied by 15 assists, piling more misery on this silly statement:
RODGERS: "We had 65% possession tonight. To me, that's more important than goals."
— Official LFC (@OfficialLFC) November 28, 2012