By Laura Saunders 

This is a tale of two similar mergers with very different tax consequences for shareholders.

One is the $34.1 billion combination of two health-care giants, Aetna Inc. and Humana Inc., announced July 3. The other is the $28.3 billion merger of two insurance giants, ACE Ltd. and Chubb Corp., announced July 1.

At first glance, the deals look alike--and like several other mergers this year. In both, the shareholders of the acquired firms, Humana and Chubb, will turn in their current holdings in exchange for about half cash and half shares, assuming regulators approve the deals. The cash payments will generally be taxable as capital gains if the investor's holdings are in taxable accounts, rather than in tax-sheltered retirement plans such as IRAs or 401(k)s.

There is a big difference between the deals, however. Humana shareholders won't owe tax on their receipt of Aetna shares, while Chubb shareholders will owe tax on their receipt of ACE shares.

Why is this? According to Robert Willens, an independent tax expert in New York, the Aetna-Humana merger contains an extra provision that allows the exchange of shares to be a tax-free swap. "This small detail makes all the difference," he says.

Here's what could happen in practice, says Mr. Willens:

Say an investor bought a share of Chubb for $45 in 2005 (adjusted for a 2006 split). In the merger, this investor is slated to receive about $64 worth of ACE stock (at recent prices) and $63 of cash in return for each share of Chubb. He or she will have a taxable long-term capital gain of $82--the difference between the investor's starting point of $45 and the total value of $127 a share offered by ACE.

If the stock portion of the Chubb-ACE deal weren't taxable, says Mr. Willens, the investor's capital gain would be $63 a share instead of $82. Because the gain includes tax on the exchange of Chubb shares, these investors in effect have to use more of the cash they receive to pay Uncle Sam.

Humana shareholders, meanwhile, will owe tax on their cash payment of about $125 a share, but not on the receipt of Aetna stock--so their tax bills will be relatively lower.

To be sure, the Chubb shareholders get a benefit in return for paying tax on the share exchange. Their starting point for measuring a capital gain, or cost basis, on their ACE shares resets higher--reducing taxes on the stock when they eventually sell it.

Because share exchange isn't taxable to Humana shareholders, their cost basis carries over to new Aetna stock. So if an investor bought Humana for $3 a share many years ago, then that will be the starting point for measuring a taxable gain when the Aetna shares are sold.

But in many cases the Humana shares won't be sold soon. And if the Humana investor holds the Aetna shares until death, no capital-gains tax will be due on appreciation up to that point because of a tax-code freebie known as "the step-up."

Some Humana shareholders say they are pleased that their deal gives them more control over the timing of taxes. Benjamin Klausing, a physician in Louisville, Ky., owns shares of very low-cost Humana stock he was given in 2002. "I'm glad I have a choice," he says.

A Chubb spokesman declined to comment on tax aspects of the merger with ACE.

What if investors in Chubb or Humana--or other mergers under way--don't want to pay any taxes triggered by the deals? Experts say there are two good options, if the investor is willing to give shares away soon.

One is to donate some or all shares to charity instead of writing a check. Donors of appreciated assets to qualified charities and donor-advised funds often can skip paying capital-gains tax and still deduct the full market value. This move can be highly tax-efficient for donors who have assets with lots of gains, experts say.

The other option is to give shares to someone in a lower tax bracket. The top rate on long-term capital gains is currently 23.8%, but joint filers with taxable income up to $74,900 in 2015 have a zero rate on capital gains, and many other taxpayers have a 15% rate.

In such a move, the giver's cost of the shares transfers to the recipient, and it becomes the starting point for measuring taxable gain when they are sold or exchanged in the merger.

But note that if the recipient is a child, "unearned" income above $2,100 is often taxable at the parent's highest marginal rate. And gifts above $14,000 to any one person a year typically are deducted from the giver's lifetime exemption, which is currently $5.43 million.

Investors considering these options should move quickly, says Mr. Willens. If the gift or donation occurs too late in the merger process--such as after the shareholder vote--then the taxable gains arising from merger will be payable by the original owner. "That would be the worst of all worlds," he says, "to give stock away and still have to pay taxes on it."

Write to Laura Saunders at laura.saunders@wsj.com

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