Terrell Owens
Last year, Terrell Owens, faced jail time for $20,000 in unpaid child support for one of his four children. Owens reportedly pays nearly $45,000 in child support per month and was confronted by three of his babies’ mothers on an episode of Dr. Phil. Owens eventually made payments, but then claimed he was too broke to continue. Besides child support drama, Owens also lost all of his East Coast property and millions of dollars due to failed business ventures.