## Facts

- Canal Corporation (formerly Chesapeake) owned Wisconsin Tissue Mills, Inc. (WISCO), a profitable tissue business with low stock basis.
- Chesapeake and Georgia-Pacific (GP) formed Georgia-Pacific Tissue LLC (taxed as a partnership).
- GP contributed tissue assets (about $376.4 million) for a 95% LLC interest; WISCO contributed substantially all of its tissue assets (about $775 million) for a 5% LLC interest.
- The LLC assumed most WISCO liabilities, but Chesapeake retained certain environmental liabilities.
- On the formation date, the LLC borrowed $755.2 million from a bank and immediately distributed the proceeds to Chesapeake as a “special cash distribution.”
- GP guaranteed the bank loan; WISCO executed an indemnity to GP intended to support non-sale treatment, and planning contemplated a minimum net-worth level at WISCO.
- Shortly after receiving the distribution, WISCO used substantial funds to repay and re-circulate cash within the corporate group, leaving roughly $157 million in assets, far less than its potential indemnity exposure.
- Chesapeake reported the distribution as a nonrecognition, debt-financed partnership distribution (rather than sale proceeds) and reported no gain in 1999.
- The IRS asserted the transaction was a disguised sale, determined a large income tax deficiency for 1999, and imposed an accuracy-related penalty for substantial understatement.

## Issues

1. Whether WISCO’s contribution of tissue assets to the LLC and the contemporaneous $755.2 million distribution constituted a disguised sale under I.R.C. § 707(a)(2)(B) and related regulations, requiring gain recognition in 1999.
2. Whether Canal was liable for the I.R.C. § 6662(a) accuracy-related penalty, including whether it had reasonable cause and acted in good faith based on professional advice.

## Decision

- The Tax Court held the transaction was a disguised sale under § 707(a)(2)(B) and its regulations, requiring Chesapeake to recognize gain in 1999 (approximately $524 million).
- The court rejected Canal’s argument that the debt-financed distribution exception applied because WISCO did not, in substance, bear the economic risk of the partnership’s borrowing.
- The Tax Court sustained the § 6662(a) accuracy-related penalty, finding Canal failed to show reasonable cause and good faith reliance on professional advice.

## Legal Principles

- A partner’s property contribution to a partnership and a related distribution may be recharacterized as a sale under I.R.C. § 707(a)(2)(B) when the distribution is effectively consideration for the transferred property.
- In disguised-sale analysis, courts examine timing, prearrangement, and economic reality; same-day borrowing and distribution closely tied to the contribution support sale characterization.
- The debt-financed distribution exception in Treas. Reg. § 1.707-5(b) requires that the distributee partner meaningfully bear the economic risk of the partnership liability; formal guarantees or indemnities are insufficient if the partner lacks realistic exposure (including adequate net worth).
- A taxpayer may avoid the § 6662(a) penalty only by showing reasonable cause and good faith under § 6664(c); reliance on professional advice must be objectively reasonable and based on independent, non-conflicted analysis.
- An opinion prepared in an advocacy posture or affected by conflicts of interest may not support a reasonable-cause defense, particularly where the taxpayer is sophisticated and understands the transaction’s primary risk is tax treatment.

## Conclusion

The Tax Court recharacterized a leveraged partnership formation with a near-immediate, debt-funded cash distribution as a disguised sale because the distribution functioned as sale consideration and the purported risk-shifting mechanisms did not place real debt risk on the distributee partner; it also imposed an accuracy-related penalty after finding the taxpayer’s reliance on its adviser’s opinion was not objectively reasonable.


Canal Corp. & Subs. v. Commissioner, 135 T.C. 199 (2010)