As the final hours of the summer transfer window's deadline day ticked to a close, the future of US international Clint Dempsey seemed precarious.
After a summer in which he upset his former club, Fulham, while posturing towards a possible new destination, Liverpool, Dempsey looked to be heading toward a season (or at least half of one) at a club that had vowed not to play him.
Hence, it was a welcome sight for Clint and his fans when Tottenham stepped up and made a deal to bring him to White Hart Lane. After all, Spurs were an ambitious side that, unlike many other top clubs in the Premier League, offered the opportunity for Dempsey to carve out a place in the starting XI.
For Spurs supporters, the move was also exciting as it brought the player who finished fourth in scoring in the 2011-12 Premier League season to a free-flowing side that had just missed out on Champions League football.
Now more than six months on from that move, it is clear that it hasn't worked out as well as either side was hoping.
After a 17-goal output for Fulham in last year's Premier League, Dempsey has just five for Tottenham this season.
While there have been flashes from Clint, the midfielder has failed to contribute as much as he is capable of at White Hart Lane.
So was this just a failed experiment for both team and player?
Only time will tell if this partnership can work out in both parties' interests.
However, there is a clear argument for why the move should not have happened in the first place.
Here are four reasons Clint Dempsey never should have come to Tottenham.
It's not as if Dempsey was struggling at Fulham before he left last summer.
In fact, the American was thriving.
His goal tally had done nothing but increase throughout his six seasons at Craven Cottage, ending with his incredible 17 league goals and 23 goals in all competitions in 2011-12.
While it is understandable that Dempsey might have wanted a change of scenery and a chance to play for a more ambitious club, the way he burnt his bridges on the way out did not make sense.
In the end, Clint was forced to make a move in order to keep playing, rather than affording himself the opportunity to wait for the best option.
Would a few more months on a Fulham side that had him playing at his best really have hurt him?
With the likes of Aaron Lennon and Gareth Bale on the wings, Kyle Walker at full-back and Jermain Defoe at striker, one thing that Tottenham look to do at every chance is counter-attack at speed.
These players fly down the pitch, trying to get the ball past defenders and create chances as quickly as they can.
While Dempsey has a lot of great attributes, this style does not seem to fit him.
In his play for Spurs this season, this has been made clear, as his moves on the counter have slowed down the break and, at times, nullified the side's greatest threat.
Now, Dempsey obviously contributes in other ways, so this isn't to say that he is an overall detriment to the side when he plays.
However, it is clear that Tottenham like to play at pace, so Clint's style of play at the front hasn't allowed him or his teammates to shine at their brightest.
When Dempsey came to White Hart Lane, the left side of the midfield already had a starter: Gareth Bale.
The Welshman's incredible abilities had him a shoo-in for the side on the left flank, leaving Clint with a more central role behind the striker.
While Dempsey has tried to do his best in this role, the fine performances he displayed in the few matches where he filled in for Bale on the left have shown that he is more comfortable in a wide role.
With Bale shifting all over the pitch and taking up a more central role over the past few matches, perhaps Clint can claim a spot on the left over the next few months.
However, at the time of his signing, Dempsey should have realized the problems that would arise from his insertion into Tottenham's lineup.
Over the course of this season, new Tottenham manager Andre Villas-Boas has proved his ability as a Premier League boss.
After a tough first attempt at Chelsea last season saw him lose the dressing room and get fired before the end of the season, AVB has done a masterful job at Spurs this season, allowing Bale to reach his potential and his side to get into position to achieve their goals.
If there is one thing that Villas-Boas has shown over his time at Spurs, it is his affinity for youth.
His system of playing a high line obviously requires mobile defenders, but the Portuguese manager has let youth reign all over the pitch.
At keeper, AVB switched from the 41-year-old Brad Friedel, who hadn't missed a start in years, to the 26-year-old Hugo Lloris. In the back, 35-year-old William Gallas went from captain to irregular starter over the course of a few months, being replaced by the likes of 21-year-old Steven Caulker.
While there is a lot to be said for this approach, it might cause some problems for Dempsey going forward.
The midfielder is going on 30 years of age and is currently on the sidelines with a slight injury.
Meanwhile, the likes of 22-year-old Lewis Holtby and 23-year-old Gylfi Sigurdsson are primed to step in and take a starting role.
Given the choice between Dempsey or either of those two playing on similar form, is there any doubt who AVB would go with?
Dempsey may have found a place to play this season at Tottenham, but he could be looking for a new club in the near future.
It is highly doubtful that that is what he had in mind when the American came to White Hart Lane.