Ashley Young was on the verge of joining Chelsea on deadline day at the start of the 2016/17 season, but Manchester United pulled the plug on the deal at the last minute. Months later, he captained the club for the first time, eventually taking the armband permanently in 2019.
Speaking on the Stick to United podcast, Young explained that he had already accepted his fate under Jose Mourinho after being told he was no longer part of the manager's plans.
Deadline Day Collapse
"I wasn't playing much... but if we had kept Louis [van Gaal] after winning the FA Cup I think things would have changed. But they didn't. So Jose Mourinho's coming in... I was out the door pretty much straight away," he said.
"Deadline day, I was due to leave. I was going to Chelsea. And between Jose and [executive vice-chairman] Ed Woodward they had said yeah it's fine, from the start of the window right up until the second to last day of the window."
Young added that a deal had been agreed with Chelsea, and he was happy to return down south because he was not playing. However, two days before the window closed, the transfer was pulled, leaving him baffled and frustrated.
From Winger to Defender
Rather than let the disappointment derail his season, Young decided to make the best of the situation. He switched from his familiar role as winger to become one of the club's most versatile defensive options.
"Then it's just getting your head around [the fact that] now I'm not going [to Chelsea], it's not happening," he said. "So come back and do everything you can. I then went from wing-back to a left back at times to a right back."
Young's willingness to adapt eventually earned him more regular opportunities under Mourinho and a position of greater responsibility within the squad.
Captaincy and Chelsea Victory
Mourinho later told Young he needed him as a senior player to take on the mantle and said he would make him captain at times. Young described the role reversal as "unbelievable," given he had been on his way out of the club.
His first outing as United skipper came against Chelsea, who were on their way to winning the Premier League title. A Young-led United produced a 2-0 victory at Old Trafford.
In 2019, Young was handed the captaincy on a permanent basis, taking over from Antonio Valencia following the Ecuadorian's departure.
Move to Inter Milan
Young's final season at United came in 2019/20, when he was tempted away midway through the campaign by Antonio Conte, who had previously tried to bring him to Chelsea. Conte, by then in charge of Inter Milan, signed Young in January 2020 and deployed him as a wing-back in his 3-5-2 system.
Inter went on to win the Serie A title in 2020/21, their first league crown in more than a decade. Young became only the third Englishman to win Serie A, following Jimmy Greaves in 1962 and Gerry Hitchens in 1963.
