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.