Former Tottenham Director Reveals How Spurs Missed Out on Jack Grealish & Frenkie de Jong

Steve Hitchen Opens Up on Two Huge Transfer Near-Misses

Former Tottenham Hotspur recruitment chief Steve Hitchen has revealed that the club came incredibly close to signing both Jack Grealish and Frenkie de Jong during his tenure.

Both players, who later moved for a combined £165 million, could have been wearing Spurs colors had things gone differently.

Tottenham’s Missed Opportunity: Grealish & De Jong

Hitchen, who played a key role in recruiting Cristian Romero and Pape Matar Sarr, spoke about the missed chances in a recent interview:

“We were very close to getting Jack Grealish, which probably would have been one of the best signings you could make. He was a Tottenham-type player—someone who would have set the place alight.”

At the time, Dele Alli was a key figure at Spurs, and Hitchen believes Grealish’s presence would have taken the squad to another level.

But the biggest what-if? Frenkie de Jong.

“We were really close to getting Frenkie de Jong as well. He would have made a huge difference for us, especially as we needed to replace [Mousa] Dembele. Frenkie could have slotted right in and been a major success.”

Where Did It All Go Wrong?

Despite Spurs’ interest, neither deal materialized. Grealish remained at Aston Villa before securing a £100 million move to Manchester City in 2021. Meanwhile, De Jong left Ajax for Barcelona in a £65 million transfer back in 2019.

Had Spurs been able to finalize these deals, would their trajectory have been different in the last five years?

What If Spurs Signed Grealish & De Jong?

Tottenham fans often wonder how things would have changed if Grealish had played alongside Harry Kane or if De Jong had replaced Dembele in midfield.

Do you think these two transfers would have transformed Spurs into title contenders? Drop your thoughts in the comments below!