[DesertCat]

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In fact being on the board at KO actually cost him billions, as he couldn't sell during the bubble because he was on the board, even though KO was clearly over valued.

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I read that Buffett actually traded a bunch of shares of BRK in 1998 for GenRE and thus profited from Berksire's inflated stock portfolio at the time. It was a very interesting transaction. And all tax free if I remember correctly because the GenRE aquisition was treated as a merger.

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The main tax benefit of using stock for an acquisition (tax deferral) accrues to the seller, not the buyer, so I don't think taxes were a consideration for Buffett in this deal. But you are likely right that he was happy to trade what he regarded as overvalued (BRK) for something he thought was undervalued (GenRe). Note that he almost always pays cash in acquisitions because he usually regards BRK as undervalued or fairly valued and doesn't want dilution. But with GenRe he did his biggest deal ever and took on huge dilution to do it when he could have used cash, so it's pretty clear he thought BRK stock was overpriced.

But of course Gen Re was nothing but problems for years after the deal, and a big part of his weak performance since the deal. He always insists on keeping management in place,so he's been very good about sizing up potential managers and avoiding deals with bad ones. In this case he blew it as he was forced to make major changes with GenRe in pretty short order. If he had a do over, I doubt he'd do this deal again.