The American came to Spurs from Fulham on deadline day of this past summer's August transfer window.
Given his relatively cheap fee and fine record at Craven Cottage, Dempsey seemed like a fantastic bargain and excited Tottenham's faithful.
Through the first few months of his career at White Hart Lane, though, Clint was a huge disappointment.
While able to go off and put in decent performances with his national team, Dempsey continuously drifted out of matches for Spurs and performed well below par. In November's Premier League clash with Manchester City, Dempsey notably disappeared, leading one to forget he was even on the pitch.
So disappointing were Clint's performances that fans of both the player and club (okay, me) began to question whether it might be time for Spurs to add depth at the position or even part ways with their newest acquisition.
Fast forward just two months to today and one can see a marked difference in the situation, as Dempsey has settled down nicely into Spurs' starting 11.
After taking over from an injured Gareth Bale on the left wing about a month ago, Clint quickly found his form. Suddenly, the American is playing to his potential and banging in the sort of goals that led him to fourth in scoring in last year's Premier League season.
In his past four appearances, Dempsey has four goals for Tottenham, including that incredible injury-time equalizer against Manchester United on Sunday.
Sunday's match with United just illustrated the sort of benefit Clint can bring to a side.
Despite wasting a gilt-edged opportunity in the second half and looking well below par on his final balls, Dempsey just kept working. And like he has done on so many occasions before, he found himself in the right place at the right time to slot in a crucial goal.
Oh, and the goal also meant that Clint scored both deciding goals against Manchester United, allowing Spurs to avoid defeat against the Red Devils in their Premier League series for the first time since the 1989-90 season.
Clint Dempsey may not be the most talented or the most influential person in Tottenham's side at the moment, but the American's constant improvement and clinical finishing have earned him a consistent place in Spurs' side.
Further, after a new transfer looked so necessary just a few months ago, Dempsey's play has presented Tottenham the opportunity to look past the position and invest in other areas of the side.
If Clint can keep up the positive trend of his play, he could soon be one of the most vital cogs of Spurs' run to a top-four finish and establish himself as one of the best bargains of the season. In addition, the potential benefits to the United States Men's National Team from such improvement would be great.
Expect more goals and improvement from the attacking American midfielder, as he gears up for a Premier League race for fourth and the start of the United States' World Cup qualifying "hex."