The Queens Park Rangers boss was linked with Leeds over the summer and now faces a tall order at Loftus Road.
The risks of a young, up-and-coming manager joining Leeds United are plentiful.
Whether any talks ever took place, Hasselbaink was always going to be better off continuing to prove himself at Burton Albion and denying Massimo Cellino the chance to sack another coach after just a few weeks (whether he deserved it or not).
Until, that is, he joined QPR instead...
On the face of it, QPR may look more stable than Leeds. Tony Fernandes prefers to stick by his managers and only reluctantly dismisses them.
But that doesn't mean the R's are in any less of a mess than United - as Hasselbaink is finding out.
At Loftus Road, the Dutchman now faces a tall order. He has been left with a poor squad whose lack of effort is simply driving their fans mad. The QPR hierarchy appear clueless and there are serious question marks over whether JFH will be properly supported in the transfer market this summer.
If he has the patience, of course, Hasselbaink can succeed with the R's. He looks a good enough young coach with plenty of potential. But he has his work cut out. Saturday's 3-1 loss to Fulham showed that.
So why pass up interest from Leeds only to take on a club struggling just as badly... It might be a bit soon to judge - but perhaps the Whites - where JFH is revered for his playing days - would have been a better choice for Hasselbaink after all?