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In season 5 of Leverage, Nate is obviously training Parker, Hardison, and Eliot to take over once he (and Sophie) retires.

In "The Blue Line Job" (S5E2), Nate asks Parker, "Well, how would you do it?" And in "The Gimme a K Street Job (S5E5), Eliot tells Nate, "I know what you're doing," referencing Nate's guidance in figuring out how to manipulate the members of Congress. But in "The Gold Job" (S4E16), Nate lets Hardison run the con and gives him guidance and encouragement when it fails.

When do Nate and Sophie (probably) actually start to train the rest of the team to take over after they retire? Season 5, or earlier?

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As far back as Season 1, Nate and Sophie are seen to be effectively trying to "cross-train" the team. Instances include:

  • "The Juror #6 Job" in season 1, where they are trying to teach Parker how to be more "normal", and Sophie is seen instructing her in persuasion techniques
  • "The Stork Job" in season 1, where Sophie coaches Eliot in grifting techniques to capture the attention of Irina, the mark (although Nate's coaching of Parker doesn't go so well as she stabs her guy with a fork)
  • "The Ice Man Job" in season 2, where Hardison tries to be the inside man, and completely overplays it despite advice from the others on how he should act

And of course, regularly throughout each season, there are regular comments about Hardison teaching the others basic computing or hacking tricks (such as teaching Eliot photoshopping in "The Wedding Job" in season 1).

It's not explicitly clear exactly when Nate and Sophie decide to consider retirement and step up the training of the rest of the team, but it could easily be from the start of season 4, once they finally get together (season 3 finale) as a couple.

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