He joined seven months ago, but arrived at a time when Boro were woefully out of form and Michael Carrick was shuffling his pack game-by-game in an effort to find a winning formula.
Whittaker was thrown straight into the starting XI to make his debut in the Tees-Wear derby against Sunderland, then dropped for the following game at Sheffield United, then reintroduced to the side for the next game against Watford. All at a time when Boro were losing and play-off hopes were fading.
On top of that, he’d had to deal with the fall-out of his Plymouth exit when then-boss Miron Muslic claimed the forward had refused to play against Burnley prior to his Boro move.
Whittaker was “devastated” by the accusation and made it “abundantly clear” he hadn’t refused to play and that it had been agreed in advance with Muslic that it was best for all concerned that he was left out.
It was hardly the ideal backdrop to his Boro arrival. And as the underwhelming second half of last season played out, Whittaker struggled to make his mark in a side that was woefully inconsistent and plodding towards a mid-table finish.
But now things feel different.
The 24-year-old returned to Rockliife for the start of pre-season refreshed after his summer break. His mindset, he says, has changed. And he instantly had a good feel about life under Rob Edwards.
“It was difficult,” he says of his first half season at the club.
“But I know I have to deal with these situations and not necessarily listen to the outside noise.
“Dealing with the end of last season and last season as a whole was difficult, but I’ve used the summer to work hard, have a break and now I feel ready.
“When I first came in it was difficult. The situation I came into was different from Plymouth. But now I’ve settled, had a good summer and want to carry on into the season.”
RECOMMENDED READING:
This, then, feels like the start for Whittaker at Boro?
“Yeah, definitely,” he says.
“It’s easy to say I only had half a season, but getting through that, I had some time off and now I feel ready to go.
“This next year feels big. From myself, I know the levels I want to hit, but we also know what we want to achieve as a team.”
It’s worth a reminder here of the levels Whittaker has previously hit in the Championship.
In the 2023/24 season, he scored 19 league goals and provided eight assists, all for a side that finished 21st, surviving by a single point.
He couldn’t repeat that last season but still scored three goals before the end of October for struggling Argyle, and hit a brilliant late winner in the surprise FA Cup win at Brentford shortly before his Boro move.
Given his dazzling Championship form, Boro, unsurprisingly, weren’t the only club in for Whittaker in January. There’d been long-term overseas interest and Burnley – who of course went on to win promotion – were pushing hard. But it was the Boro move that most appealed, and it was seen as a real coup at the time.
Despite his difficult first few months at Boro, when you consider what went before then there should surely be excitement at what Whittaker can achieve this season, especially now he says he’s playing with real belief.
“Getting the goal and assist in the first friendly (at Mansfield) was a massive help for me,” he says.
“I think I’ve shown this summer I have the confidence and I’m not being indecisive. That’s the level I’m at now and hopefully I can take it into the season.
“A lot of that has come from me, just believing in myself and not letting outside noise affect me.
“I had a good summer off, worked hard and changed how I looked at certain things. And Rob coming in has been a big help as well. He’s given me the freedom to play how I want to play and to be ourselves.”
It’s still relatively early days, but Whittaker likes how things feel under the new head coach.
He says: “It’s been really good. He knows the quality we’ve got, he’s just tweaked certain things throughout the summer.
“With the formation we’re playing, he’s allowing us [the attackers] to all play together and to have that freedom. It’s really good. I think we’ve got the right balance.
“As a team we have so many individuals who can make it difficult for teams. Rob has given us the freedom and wants us to be unpredictable. It’s hard for defences to deal with that.”
