Dempsey's wait for a deadline-day transfer paid off. Not only did he join a traditionally more competitive team, he'll earn a far more competitive salary.
The United States national team forward completed a switch from his previous club Fulham with just minutes left before European soccer's trade deadline expired after agreeing to a contract worth an estimated $22.2 million over three years.
The terms of EPL contracts are not made public, but a source close to the deal confirmed that Dempsey is committed to Tottenham until 2015, with Fulham receiving a transfer fee of $9.6 million as compensation for losing its biggest star.
Brad Friedel was previously the highest-paid American, with the goalkeeper having earned $6.59 million per season since he joined Tottenham last year.
Friday's deal brought to an end a transfer saga that had rumbled on for most of the summer off-season, with Liverpool the strongest contender for Dempsey's signature for much of that time. Fulham even put in an official complaint about Liverpool's conduct after a story appeared on a club-related website insisting a move was imminent.
Another EPL team, Aston Villa, also got involved in the action, having an $11 million offer accepted by Fulham, before Dempsey quashed that deal by refusing to move to the Birmingham-based club.
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In the end it was the last entrant into the race that got the prize. Tottenham left it late but came in strong on the final day of the transfer window and provided the 29-year-old Texan with the kind of move he was desperate for.
After five years of outstanding service for Fulham, it was, quite simply, time to move on for Dempsey. The west London club served him well, allowing him to blossom from an unproven youngster fresh from the NCAA college system (and then a brief stint in Major League Soccer) into one of the finest players in the EPL, arguably the world's best domestic club competition.
"To play under [Tottenham head coach Andre Villas-Boas] and play for this club is a dream come true," Dempsey said. "I want to make the most of it. There are a lot of great players here; I'm looking forward to training and playing with them."
Dempsey deserves huge credit himself for having forged such a productive spell in Europe, and few will begrudge him this opportunity to take another potential step forward in his career. Along with Landon Donovan, Dempsey is part of the core of the national team and has always delivered loyal and passionate service to his country, having taken part in the 2006 and 2010 World Cups.
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Now he has the chance to elevate himself to the next level, and this move will also add to his profile stateside. Though most EPL games are available on U.S. television, Tottenham draws a considerably bigger audience than Fulham.
Furthermore, the north London club is likely to challenge for a place in the Champions League next season. Indeed, it would have been in the event this year after finishing fourth in last season's EPL. However, Chelsea's victory in the Champions League final meant the Blues, not Tottenham, took the last English qualifying place.
Dempsey's transfer will be rubber-stamped on Saturday, assuming he passes a physical examination that should be little more than a formality. Neither he or fellow new signing, French goalkeeper Hugo Lloris, was available to play for the club against Norwich City on Saturday.
Last season was Dempsey's finest yet in England and provided further confirmation of his rising star. A return of 17 goals in 37 games was impressive in itself, but more than anything it was his confidence and no-nonsense approach that won the most plaudits. The irony of this move and his newfound status as the highest-earning American soccer player is that financial reward is one aspect that seems to mean less to him that many of his fellow professionals.
For him it has always been about the improvement and the challenge, which is why this move and the chance to fulfill the dream of playing for a big club will be extra sweet.
Martin Rogers is a soccer columnist for Yahoo! Sports