Yes, but the pro rating vs isolation of basis issue is not real clear due to confusing IRS guidance in Notice 2009-68 and tax code provisions. There are several ways to do this, some less risky than others. But even the most risky methods have not produced any IRS challenges in the last 5 years. In the following order from safest to most risky, here are the options:

1. Client asks for a single distribution paid to him. 15k will be withheld for mandatory 20% withholding, so he receives 85k. He then first rolls 75k over to his TIRA, and then he must replace the 15k to roll the 25k to his Roth IRA. 15k is recovered when he files or sooner by reducing current tax payments. This is protected by the tax code Sec 402(c)(2) which states that the first dollars employee rolls over are deemed to be the pre tax portion of a distribution made to employee.
2. Client does a direct rollover of entire balance to a rollover TIRA if his current employer will accept IRA rollovers. He then rolls the pre tax portion of his TIRA to current employer’s plan and then converts the remaining basis of 25k or any other basis he has in his TIRA from non deductible contributions. No withholding to deal with.
3. Tandem direct rollovers (pre tax first) as you described. This is the most risky because 402(c)(2) only applies to distributions made to the employee. Direct rollovers are not made to the employee. If client wants to do this despite added risks, it should be done late in the year when it is too late for the IRS to change the 1099R reporting instructions for the current year since employers will not have time to change their payroll systems.

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