Ex-Middlesbrough and Leeds United striker questions Jonathan Woodgate's decision plus loanee impresses against Portsmouth
Woodgate was relieved of his duties as Boro head coach last month after just over a year in charge at the Riverside, and Hasselbaink believes the former defender needed more experience around him.
The Dutchman told Sky Sports: “I know Steve Gibson very well. Brilliant man. He has given Jonathan the opportunity, he has also given him as long as possible.
"Do I think Jonathan has been smart by putting Keane as his assistant? No. In his first job, he needed a more experienced person next to him. That’s what I would’ve done.
"Hindsight’s a brilliant thing and it’s now easier to talk about it. If it was me, I would’ve had someone a little bit older with years of experience next to me because it is a big job.”
"Even though they were not going for promotion, it’s still a big job. Changing the play-style and having a lot of good players.
"They shouldn’t be in the position that they are, even with the change of style.”
Former England stopper highlights Warnock asset
Rob Green believes Neil Warnock’s man-management skills will help Boro survive in the Championship this season.
Green, who retired from the game last year, remembers playing against Warnock and says it was always a challenge against his sides.
“I used to despise playing against Neil Warnock’s teams because every game was a fight,” Green told BBC 5Live. “Everyone I spoke to who played under him said ‘I tell you what, you’ll really enjoy playing under him.
“To be fair, I did. He’s a good guy, he’s been around football for a long time and if there was anyone who could even think about keeping Middlesbrough up, I’d put my money on him.
“The tactical side, the side that you see with Pep Guardiola and Jurgen Klopp, is something that he has but not at the forefront. What he does have is the other side, he puts his arm around the players and speaks to them, makes them feel good about themselves.
“If you’re struggling as a player, as Middlesbrough are, those guys will have their confidence shattered at the moment, it will be really low. You need a manager to come in and say ‘I believe in you and make you feel amazing’.”
Browne on target in play-off draw
Finally, Boro loanee Marcus Browne produced a fine display in the first leg of the League One play-offs on Friday night.
The 22-year-old re-joined former club Oxford United in January and has impressed since returning to the Kassam Stadium.
Browne helped The Us climb to fourth in the table before the season was suspended in March, contributing with four goals and four assists.
And Browne was on target once again as Oxford came from behind to draw 1-1 with Portsmouth at Fratton Park.
The second leg of the play-off semi-final will take place on Monday, July 6.