The son of a Brazilian footballer and a product of the famed La Masia academy there was little doubting his ability when Spurs splashed out €6 million to bring him in from Barca in 2008.
However in his four years at Tottenham he managed to make even less of an impact then he did at Barca. In fact the playmakers most impressive times came away from the club whether at Ipswich or Racing Santander; or on international duty with Mexico.
Last summer Tottenham finally took the plunge and sold the former starlet to La Liga outfit RCD Mallorca for a fee of €1 million. But again for the first half of the season it looked as if this was another false dawn for Dos Santos who initially struggled at his new club.
However he has turned it around since the New Year. After scoring his first goal for the club in January he has become a regular feature in the starting line-up; playing the entire 90 minutes in his previous 19 La Liga matches.
Despite his upturn in form Mallorca are still struggling and this weekend will be relegated should they fail to win against Atletico Madrid and Deportivo manage to pick up anything at Malaga.
So with the Balearic club teetering on the edge of a relegation precipice it seems the vultures have already started circling around the former Spurs man.
According to reports Valencia are leading the way for his signature but Real Betis and Atletico Madrid are also keen on snapping him up ahead of next season.
The reports suggest Dos Santos has no desire to leave the Iberostar Stadium unless relegation occurs but if his current team do fail to beat the drop it appears Dos Santos will be on his way.
But that is not where the story ends.
When Tottenham sold the Mexican to Mallorca last summer they agreed to retain 50% of his next sale for themselves. Mallorca took the risk in order to bring the price down and now the cash-strapped La Liga outfit look like struggling to make anything other than what they paid for their star in the summer.
For Spurs it could be very good news. With a couple of extra million Euros likely to fall into their coffers this summer.
But perhaps more intriguing is Valencia’s interest. With their striker Roberto Soldado increasingly linked with a move to Spurs this week a deal could be struck between the three parties so that everyone wins.
With Mallorca wanting 100% of the fee and Valencia wanting Dos Santos Tottenham could effectively say yes to both; as long as the price on Soldado drops considerably.
It is an interesting situation that should certainly be monitored closely; starting with Sunday’s results from La Liga.
image: © Pedrito Guzman