Contrast that begging-bowl approach with how smoothly the deal-making went this time round. "I've never seen a move happen so quick," said Cleverley. "I trained with Everton on Wednesday afternoon and then by the following morning, at 6.30am, I was getting a knock on the hotel door in Watford from the doctor saying he wanted to get the medical started.
“It happened that quick. I'd gone from not knowing there was a sniff of Watford being interested to being at the training ground the next day and Vicarage Road two days later."
Cleverley said his agent didn't need to ask him twice if he fancied the move. As soon as he put the phone down, he packed a bag, drove to Everton's Finch Farm training ground, collected his boots and headed south.
"I just jumped at the chance," he said. "It was the chance to play Premier League football for a club I know well and a club I really enjoyed playing for. I was delighted. I just want to play and do well.
And didn't he do well in his last stint; scoring 11 goals in 35 appearances, a ratio some strikers would be proud of.
"It was the best period I've had of goalscoring in my career," he said. "It was down to where I played, confidence and it being that bit easier to score as a midfielder in the Championship than it was in the Premier League. It was a really good moment of my career. I hope I can get those feelings back."
Mackay feels Watford are getting a good egg as well as an established box-to-box homegrown midfielder. "Within ten minutes of training on day one with us, I said to Sean Dyche 'we've got one here'. He was terrific around the place, always smiling. He was an absolute pleasure to work with and was a star for us."
So much so that he romped the Player of the Year award. "It's definitely one of the major achievements in my career," said Cleverley. "I've got the matchday programme I was on the front of and I've got the [winner's] plate on a stand in my trophy cabinet."
Now 27, Cleverley has since won 13 England caps, won the Premier League, played in an FA Cup Final, got married and had two kids. He's hungry for more professional success, much more, and found a man whose ambition is very much aligned to his in Gino Pozzo.
"Speaking to him for just five minutes you can see how passionate he is about football and about progressing the club. It's something I want to be a part of and hopefully we can make things permanent in the summer."
The ownership of the club has changed since Cleverley was last in these parts but some things remain the same. "I knew Mapps [Adrian Mariappa] and Craig [Cathcart] and I kept in touch with Jonesy [Will Jones] the kitman so it's been easy for me to settle back in," he said.