Having left the Emirates for Manchester United in controversial circumstances three years ago, the Dutchman has now been shipped off to Fenerbahce.
It is likely that the 31-year-old would say, no, he is happy to take in a new adventure, or no, his decision was vindicated by his title win in 2013.
But look a little deeper and there are plenty other high profile Gunners players who pushed for a move away from the club, only to find that life wasn't so greener, or patient on the other side.
In fact, if you look at the list of Arsenal's big exits over the last few years, practically all of them have ended up as less important figures than they would have hoped to be at their new clubs, or even moved on from the side they signed for.
In contrast, the Gunners, in spite of their sales, are now in a position where they should be challenging for the league again next season.
Van Persie, Samir Nasri, Gael Clichy, Alexander Song and Cesc Fabregas, all left the club between 2011 and 2012, and except for Fabregas, each has seen their footballing career begin to stutter within three seasons of leaving the Emirates. Even the Spaniard's homecoming to Barcelona was much more short-lived than he expected it to be.
Would all these players say they were right to move because they won league titles, even if their football careers became less certain and, on a personal level, less successful soon after?
Clichy and Nasri, despite winning league titles at Manchester City, have seen their importance at the Etihad dwindle recently, while Alex Song was on loan at West Ham last season.
Van Persie of course, was a key man when United won the league in the season immediately after he left Arsenal, but niggling injuries soon kicked in, and despite the arrival of his favoured coach Louis van Gaal, the 31-year-old was deemed dispensable enough to offload to Fenerbahce for a low fee.
The Dutchman may be valuing his Premier League medal as his most treasured honour, and well he might, but if he would have remained with Arsenal, ensuring his legacy at the club remained unblemished, he would have likely had at least two FA Cup wins to his name to provide compensation.
But even more importantly than that, he would not have been offloaded by Wenger after having a season dealing with injuries. Additionally, he could have been the striker many would say Arsenal still need in order to make that genuine step up to challenge for the title.
As he prepares to start his new season in Turkey, Van Persie may just be thinking that he should have been happy with what he had in North London.