By hijacking the deal from Liverpool, Spurs left a potential threat to its top-four pursuit reeling. Further, the modest £8 million transfer fee seemed a bargain for the fourth-highest scorer in the 2011-12 Premier League season.
On the American side of the spectrum, the deal allowed Dempsey, one of the US national team's most important players heading forward in its World Cup pursuit, to get even more experience in upper-echelon matches.
It all seemed so promising.
Fast-forward two-and-a-half months and 11 Premier League matches to today and the outlook has all changed.
Through seven appearances, Dempsey has failed to really stand out for the club. Fans of the American might point to his two goals, each of which were road match-winners (against Manchester United and Southampton), but even those were mere tap-ins off the back of his teammates' good work.
Before Sunday's match with Manchester City, a slight discontent could be sensed from Spurs supporters who wanted more from their (not-so-) new signing.
Then came perhaps the most lackadaisical performance yet from "Deuce," as he completely failed to show up against City, sending Tottenham supporters into a frenzy.
The best summary of Dempsey's performance actually came from my dad, a relatively new football fan. After being brought to the edge of his seat by the action, my dad called me in the 80th minute and asked, "Wait, Dempsey is playing?" Apparently, he didn't even realize this until the camera zoomed in on Clint late in the match. That pretty much says it all.
So the question becomes clear: What should Tottenham do with Dempsey?
The question has become a polarizing one. Since the end of Sunday's match, upset Spurs fans have made their feelings all too clear. Some want Dempsey benched, others go so far as asking for his transfer come January.
On the other hand, fans of the US team have defended Clint, wanting Tottenham to stick with its man for fear of the impact his dropping might have on the national side.
So let's analyze every option for Spurs.
Obviously, an option is to keep Dempsey as a starter and look to grind out his poor form. In some senses, this makes sense. After all, Spurs don't have the greatest options behind him, what with Gylfi Sigurdsson in similarly poor form and a second striker representing a change in systems.
However, there is a clear risk of Dempsey not coming out of the slump, which would cost his side dearly.
Another possibility is for Tottenham to drop Dempsey and let him work out his problems on the training ground and in lesser competitions (i.e. FA Cup, Europa League). Perhaps Sigurdsson could find his form or Andre Villas-Boas could adapt his tactics to fit two strikers.
However, these raise almost as many question marks as are created by Dempsey.
Finally, the club could just give up on the American, put him on the transfer block come January and get a new face in the window. This is of course appealing given the excitement of getting a new face in the door.
However, it's tough to expect a deal with a top attacking midfielder in a January transfer window.
So what should Spurs do?
This is a tough one for me. I really don't like the idea of selling Clint in January. I doubt Tottenham would be able to get much in and I think it would be far too early to give up on a signing. I am really intrigued by a Jermain Defoe-Emmanuel Adebayor partnership up top, but that is up to AVB.
From the other options, it comes down to what you think is plaguing Dempsey. Perhaps it's that he still isn't familiar enough with his teammates, but I'm more inclined to believe that Spurs' fast style just doesn't suit him.
To me, I would sit Clint for Sigurdsson and let him earn back his first-team spot.
Let's just hope he finds his feet from there, or he may be out the door come next summer.
What do you think Spurs should do with Dempsey? Let me know in the comments below.
For the latest news in the world of football, follow me on Twitter.
Like the new article format? Send us feedback!