England legend Pearce was a coach at West Ham during Lingard's six-month loan in which he was one of the best players in the Premier League.
The attacking midfielder managed nine goals and four assists in just 16 games, helping the Hammers finish the 2020/21 season on a high.
They secured a Europa League spot and almost converted that into a trophy win last term.
They had to do so without Lingard though, as the 29-year-old ended his loan to return to parent club Manchester United where he barely played.
Lingard is now a free agent after the expiration of his contract at Old Trafford, and Pearce thinks a return could still be on the cards.
Asked by talkSPORT's Natalie Sawyer if Lingard's time at West Ham is 'done,' he replied: "I'm not sure whether it's totally done or not.
"We might have had the best six months out of Jesse Lingard that he's ever going to have in football, again or beforehand.
"He was magnificent for us, he gave us a slightly different dimension, his football was outstanding.
"He's got a footballing arrogance, Jesse. He'll take the ball anywhere on the pitch and it was a massive disappointment that Jesse didn't come and join us permanently in the summer on the back of that."
Pearce was then asked if West Ham tried to re-sign Lingard to which he said: "Of course, and so will various other clubs.
"He'll end up going where he wants to go, West Ham got him and his performances got him back in the England fold which he hasn't been in and he's very proud of.
"We talk about Danny Drinkwater in an extreme case of not having enough football over a certain amount of time but I look at Jesse and Jesse's ability and think he's been on the outside of it at Manchester United for a calendar year and I find that a shame.
"It was almost a kindred home, he enjoyed the environment, he was loved at the club, he respected Dave and playing for Dave and the demands Dave puts on players."