iHeart
Moved 100 million shares, worth $516 million, to an unrestricted subsidiary using the investment permissions in its bonds; the subsidiary then bought back iHeart's bonds at a deep discount. A Texas court upheld the transaction in Franklin Advisers v iHeart.
Discussed in Liability Management Exercises: Law and Practice at ¶¶ 2.91, 2.103, 2.145, 2.151–2.153, 5.92.