Tottenham are believed to be on alert over the possibility of signing another free agent who Mauricio Pochettino nearly brought to north London years ago.
Spurs already agree conditional Robertson and Senesi deals
If Spurs survive on Sunday — and one point against Everton will be enough — the summer rebuild will begin immediately.
Roberto De Zerbi has already laid the groundwork.
Verbal agreements are in place to sign Liverpool’s Andy Robertson and Bournemouth’s Marcos Senesi on free transfers, with both deals contingent on the club retaining their Premier League status.
Robertson, 32, brings experience, leadership and nine years of competing at the highest level at Anfield.
Senesi, 29, adds proven top-flight quality at centre-back after four impressive seasons on the south coast. Neither deal has been formally signed, but the terms are agreed, and both players have committed to joining the project if Spurs stay up.
De Zerbi personally wants Tottenham to sign £20m star who dominated Arsenal
The Italian is a big fan.
Now, a third free agent has entered the conversation, and this one carries a familiar backstory.
Tottenham eye shock free deal for Paulo Dybala
According to Football Insider’s Pete O’Rourke, Tottenham are eyeing a move for Roma forward Paulo Dybala, whose contract at the Stadio Olimpico expires at the end of June as things stand.
The “top” Argentine has been a long-standing target for the club, and sources have told the outlet that Spurs could look to capitalise on his availability as they reshape the squad under De Zerbi.
Dybala has had a frustrating final season in Rome.
Injury problems have limited him to 26 appearances, 16 starts and just 1,504 minutes across all competitions.
Three goals and six assists represent a modest return by his own standards, though his quality on the ball — the vision, the creativity, the ability to unlock a defence with a single pass — has never been in question.
Roma have discussed a one-year extension on reduced terms, but nothing has been signed and Dybala is expected to assess all of his options once the season concludes.
Boca Juniors are also interested in bringing him back to Argentina.
What gives this story an extra edge of shock is the history.
In the summer of 2019, during Mauricio Pochettino’s final months in charge, Tottenham came agonisingly close to signing Dybala from Juventus.
The deal was virtually done — personal terms had been discussed, the structure of the transfer was in place — before it collapsed on deadline day over complications surrounding the player’s image rights.
It was one of the most dramatic near-misses of that window, and the sense of what might have been has lingered at the club ever since.
Seven years on, the circumstances are very different.
Dybala is no longer the 25-year-old who was lighting up Serie A as one of the most exciting forwards in European football. He is 32, his body has let him down more often in recent seasons, and O’Rourke acknowledges that his age and injury record may put some clubs off.
But on a free transfer, with no fee involved and the wages negotiable, the risk-reward calculation shifts considerably.
De Zerbi is building a squad that needs creativity, experience and players who can perform in high-pressure moments. Dybala, for all the question marks around his fitness, has 40 Argentina caps, and a World Cup winner’s medal.
First, Sunday. Then the contracts. Then, perhaps, the deal that got away finally gets done.
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