I just don't really think that Dempsey suits Spurs that well. He's more of a positional type player where as the rest of the Spurs team are all about pace and being very direct. When Spurs are in full flow or on the counter attack whenever I have watched him he appears to just get left behind a bit, only being effective on the followup or coming into the box late.
This is what you need, desparately, Adebayor he had his good games, and the other games when he couldn't hit a barn door, you need someone to arrive late in the box and take the shot. Modric rarely did that, Parker doesn't do that, Sandro doesn't do that. That is a CRUCIAL role that you are both overlooking as not being a good thing.
How many games, and how many titles have Chelsea won because Lampard gets the winner by doing exactly this? its the guy who makes the smart run unnoticed by everyone else, who gets the goal. Scholes for Utd(obviously much less so now but in his first decade, it was crucial to Utd and his game), for Barca you have Xavi, Cesc, Iniesta, Busquets, just about anyone there is capable of that role, City have Yaya/Milner, Liverpool HAD Gerrard for this.
It is a fundamental, crucial thing that players do, when everyone with pace simply bursts up the field, then either shoots or crosses, the when that shot or cross sucks or gets palmed out by the keeper or a weak clearance, its the guy late into the box that gets so many winners.
Thats exactly what he did for Fulham so often, and its EXACTLY what Spurs needed last season, when Bale took 762 shots either missing or hitting the bar, when you ran out of idea's, its a guy like Dempsey that would have got you winners during that spell of poor form.
Like I said though, he's had no preseason, was geared up to move to Liverpool, got frozen out, didn't play till he joined you and he's really not played an awful lot with Dembele has he? Dembele joined having been a part of Fulham's season while Dempsey didn't, Dembele came into the team match fit and in form, Dempsey didn't, its always easier to join a team match fit and with form, than without.
Also in comparing him to Modric, and the fact he offers you a lot more potential goals than Modric did... this was a player you guys loved, whose game was nothing to do with direct play and pace. A team full of players that are only about pace and direct play, is a team destined to fail.