Arsene Wenger says Alex Oxlade-Chamberlain's Arsenal exit was not as painful as Kieran Gibbs' departure to West Brom.
Gibbs left for the Hawthorns in a £7m deal on the penultimate day of the transfer window, with Oxlade-Chamberlain following him out the door when he made a Deadline Day move to Liverpool for £35m.
Full-back Gibbs came through the ranks at Arsenal before breaking into the first team at 18 and going on to represent the club 230 times in all competitions.
Despite Oxlade-Chamberlain featuring more than Gibbs under Wenger last season, Wenger admitted losing Gibbs hurt him more.
"Ideally you want stability and you want players who carry the values for the generations," Wenger said ahead of Gibbs' return to the Emirates with Tony Pulis' West Brom, live on Monday Night Football.
"Overall it's true that with Gibbs (it hurt) more than Chamberlain because he had been educated at Arsenal from the age of 10.
"When he arrived he was a left-winger. I transformed him into a full-back because he was not necessarily rated as a guy who would make it as a left winger but I saw something in him that was very intelligent, with pace, that made me feel he could make it as a left-back.
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"(Academy players) carry the values that you think are important, which are based on mental qualities, humility, respect and commitment, and as well football qualities which means you always try to play in a positive way. Plus real team play and focusing on a collective way."
Gibbs was limited to just 11 Premier League outings last season and the summer arrival of Sead Kolasinac was always likely to force the 27-year-old out of the club.
A move to Watford failed to materialise before West Brom stepped in on the eve of deadline day, with Wenger gutted to see Gibbs move on.
Asked if letting Gibbs leave felt like losing a family member, he said: "Of course. And I believe that for (players that leave) it must be difficult to make that step as well.
"He did not ask to leave, it was a mutual decision. He wanted to play - he's 27, or 28. You want to play at that age.
"It was a difficult decision but on the other hand when a guy has given you so many years you have to accept that if he is not sure to play.
"It is a fact that we have got Kolasinac, you cannot keep three left-backs (along with Nacho Monreal)."