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Your memory is correct. Only a single non-trustee-to-trustee rollover is allowed in any 12 month period. So he could only do that for one of the pensions.

Additionally, if the pension plan writes out a check to him, they will likely be required to withhold at least 20% in Federal taxes, and your state may also require withholding. If he wants to roll the entire amount over, he will have to come up with the cash to make up for that withholding. With a trustee-to-trustee rollover, withholding is not required.

I re-read one of my Ed Slott books on IRAs to see what stuff I highlighted in 2018 became obsolete last December with the SECURE Act. Let me confirm that aj is correct on the one non-trustee-to-trustee rollover per year rule. Also, it sounded like doing a non-trustee-to-trustee rollover from IRA to IRA will sometimes result in 20% being withheld for federal income taxes. But, with a non-trustee-to-trustee rollover from 401k to IRA, there will *always* be 20% withheld. So, you have to come up with that 20% to put into the new IRA or get dinged with a withdrawal, triggering taxes and possibly penalties.

Why risk misplacing the paperwork, or getting sick, or whatever, and missing the 60 day window? Do the trustee-to-trustee transfer.
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