Frank Lampard has now taken the hot seat at Stamford Bridge following the end of his playing days with the club, and the year at Derby County.
Whilst Christian Pulisic left Germany and swapped life to England in a £58 million deal which was agreed between the two sides prior to the Blues being slapped with a two-window transfer embargo.
The 21-year-old has found it difficult to cement a spot in the first-team as a regular starter, despite having played five times in the Premier League, and bagging four assists in all competitions - with the latest coming last Sunday for Michy Batshuayi in the 4-1 win at Southampton.
But BBC Pundit Chris Sutton, speaking on BBC Radio 5 Live believes the American star will have serious problems getting into the Chelsea side, and questioned whether Frank Lampard would've signed him had he'd been in charge in January.
"[Christian] Pulisic has to prove himself," Sutton said on the 21-year-old.
"He wasn’t Frank’s signing, of course. With Callum Hudson-Odoi and Mason Mount coming to the fore, he’s going to have a major problem getting into the starting line-up. I really do think that.
"I don’t see a way in for him at the moment. It’s a lot of money to spend and it would be interesting to ask Frank now if he would sign him at this moment in time if he hadn’t signed him before?
"The answer to that, I think, is pretty obvious – he wouldn’t."
Despite this, the Chelsea winger is confident his time will come at Stamford Bridge, and hasn't lost hope just yet: "Obviously, I haven’t been getting as many minutes as I would like," Pulisic said.
"I will just keep going, keep pushing. I know my time’s going to come."