The former Tottenham midfielder had been made aware of the image containing his talkSPORT co-host and used it to his advantage - as all good friends would.
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He is seen posing with four West Ham fans alongside a custom Irons flag but that wasn't the big flashpoint of the picture.
Cundy - a die hard Chelsea fan and former Blues player - was captured doing the famous Hammers pose of making an 'x' with his arms.
Never one to pass up an opportunity to banter his co-host, O'Hara uploaded the picture to his Twitter account on Thursday night.
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O Hara's caption read: "Jason Cundy is now a West Ham fan, we found the picture absolutely shocking from him."
It has been an eventful couple of days for Cundy who has found himself on the receiving end of multiple jokes.
Cundy was in Madrid on Wednesday to watch his beloved Chelsea lose 2-0 against Real in their Champions League quarter-final first-leg.
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Following the defeat, Cundy told talkSPORT of his struggles to buy a drink in the Spanish capital.
But it got worse. The 53-year-old was later kicked out of a bar mid-interview, to the enjoyment of the talkSPORT studio.
Chelsea have the opportunity to end Cundy's week on a high note when they entertain Brighton this weekend.
The Blues must win to keep alive their faint hopes of European qualification next season.
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However, it remains to be seen whether Cundy will have one eye on West Ham's trip to Arsenal on Sunday.