Florida Tax Attorney Blog

A bond swap is a tax and investment strategy whereby an investor sells a bond that has declined in value and simultaneously purchases a substantially similar bond with the proceeds from the sale.

Why?

If an investor plans to use the proceeds of the bond sale to purchase a substantially similar bond, why not just hold the existing bond? The reason is purely strategic. By engaging in this type of transaction, the investor generates a tax loss. This artificially generated tax loss can be used to offset capital gains and ordinary income without altering the general composition of the taxpayer's investment portfolio.

Here's How It Works:

Step 1: investor sells a bond that has declined in value.

Step 2: investor simultaneously purchases a bond with substantially similar attributes in terms of principal amount, yield, and recovery period.

Following this transaction, the investor continues to own a bond with substantially similar investment characteristics and also holds a tax loss that can be used to reduce his or her income tax liability. The tax loss realized on this transaction can be used to offset capital gains realized on other investments. In addition, to the extent the loss exceeds capital gains, it can be used to offset up to $3,000 of ordinary income. SeeInternal Revenue Code §1211(b). Any loss beyond that can be carried forward and used to offset capital gains and ordinary income in future tax years. SeeInternal Revenue Code §1212(b).

IRS May Challenge Bond Swap Transactions Under 2010 Legislation.

Investors have been engaging in bond swap transactions for years in order to trigger tax losses without altering their overall economic positions, and this practice has generally been accepted by the IRS. Moreover, the United States Supreme Court has seemingly endorsed this tactic. See Cottage Savings Association v. Commissioner (upholding mortgage loan swaps by banks to realize tax losses). But recent additions to the Internal Revenue Code have raised questions about the continued propriety of this tax and investment strategy.

In 2010, Congress codified the common law economic substance doctrine in Section 7701(o) of the Internal Revenue Code. Under the economic substance doctrine, tax benefits are denied if the transactions giving rise to the benefits lack economic substance apart from tax considerations. Pursuant to Section 7701(o)(1), in cases where the economic substance doctrine is relevant, a transaction shall be treated as having "economic substance" only if: (1) the transaction meaningfully changes the taxpayer's non-tax economic position; and (2) the taxpayer has a substantial non-tax purpose for entering into the transaction.

Because the bonds swapped are substantially similar and because the sole purpose of a bond swap is to create tax losses without changing the investor's overall financial position, this type of transaction is subject to challenge under this new legislation.

Bond Swaps Probably Remain Acceptable Despite 2010 Legislation.

Notwithstanding the 2010 codification of the economic substance doctrine, bond swaps probably remain safe tax and investment strategies.

First, in order for the IRS to invoke Section 7701(o) to challenge a bond swap transaction, the statute requires that the economic substance doctrine be "relevant" to the challenged transaction. Based on the pertinent case law, the economic substance doctrine is arguably irrelevant to a bond swap transaction. Indeed, in Cottage Savings, the Internal Revenue Service raised the economic substance doctrine in opposition to a bank's mortgage swap transaction, but the Supreme Court declined to apply the doctrine. Moreover, the Supreme Court seemingly rejected the relevance of the economic substance doctrine in swap transactions when it stated that, "a much less demanding and less complex test" is required.

Additionally, even if the economic substance doctrine is relevant to bond swap transactions, this type of transaction arguably possesses economic substance and business purpose apart from tax considerations in the sense that, although similar, the two debt instruments differ in the sense that they represent different debt obligations and have different issuers. Moreover, swap transactions have substance beyond the tax considerations in the sense that the swap itself is a mere component of a larger transaction of deriving a desired rate of return on the overall investment portfolio.