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Lieberman was elected in 1988, not '98, when he beat Weicker very narrowly. William F. Buckley (a Sharon, CT resident) and friends were behind Lieberman's victory. An ultra-conservative Democrat was preferable to them over the very progressive Republican Weicker. Lieberman's Democratic credentials are non-existant even if he was Gore's running mate in 2000, itself miraculous given that Gore won the election.
Weicker retaliated against Buckley & Co. by becoming governor of CT, as an independent, and instiuting an income tax, which probably took several years off Buckley's life. Weicker chose not to run again having accomplished his biggest goal.
If Weicker does run for the Senate again, assuming Lieberman isn't Secretary of Defense by then, and/or an announced Repug, he will surely do it as an independent voting with the Dems. Looks like great political theater to me.