Crossing the Arsenal/Tottenham divide is a move that few have dared to embark on and Jack Wilshere will not be joining either William Gallas or Sol Campbell down that rarely trodden path.
Who would have the nerve to betray their former club by joining their fiercest local rivals?
Luis Figo and Carlos Tevez joined Real Madrid and Manchester City respectively in two of the most controversial transfers in the history of the game, tainting any relationship they may have had with Barcelona and Manchester United in the process.
Only a small handful of players have irked Spurs or Arsenal fans by playing for both clubs, with Campbell being the most high-profile example.
Though he is unemployed and searching for a new club as a free agent, Wilshere has claimed that he wouldn't turn his back on the Gunners by moving to Spurs.
While speaking to the Sky Sports Super6 podcast, the 34-cap England international spoke of his admiration for Jose Mourinho but conceded that the Premier League title challengers wouldn't be willing to take him on even if he was willing to put his allegiances to one side.
"I love [head coach Jose] Mourinho, I think he's an unbelievable coach... But I couldn't do it.
"They wouldn't have me!" he said. "But I don't think I could do it. It's not as if Arsenal got rid of me and kicked me out and there is bad feeling, they offered me a deal and I wanted to try something else. I'm an Arsenal man."
Wilshere's gushing words of praise for Mourinho arrive during a time when the Portuguese manager is beginning to re-establish the level of respect he once unanimously commanded across the game.
Criticisms of his perceived negative style of play have tainted his reputation in recent years, but the fact a player of Wilshere's technical ability has spoke so highly of him suggests his meteoric standing remains in tact.
On the subject of his future, the creative midfielder suggested he is willing to move abroad to kickstart his career once again.
"It is important to find a club where I am going to play, be an important player and be happy. I don't want to rush into anything. It has to be the right team in the right country," Wilshere said. "I am open to Europe or wherever.
"People forget I am 28. Everyone thinks I am 30 or 31, probably because I started when I was 16. That is 12 years ago, which is a long time in football."
Given how his stint at West Ham petered into insignificance, it seems unlikely that he'll be offered another chance in England's top flight.
Whatever Wilshere decides on, we certainly won't be seeing him under Mourinho at Tottenham.