Underwood was born in Philadelphia on March 29, 1977, the youngest child of Paul, a former insurance salesman, and Eileen, an information specialist at IBM. The family would move to upstate New York, and later to his father's hometown of Fayetteville, North Carolina, after Eileen was laid off from her job. He attended E.E. Smith High School. As a senior defensive tackle, he posted 87 tacklesand 10sacks, receiving honorable-mention All-state and All-Cape Fear Region honors. He also practiced wrestling, finishing second in his weight class at the 1993 state meet.
College career
Underwood accepted a football scholarship from Michigan State University, to play under head coach Nick Saban. He was a reserve player as a true freshman, appearing in 11 games and making 9 tackles. He became a starter at left defensive end as a sophomore, tallying 37 tackles and 5 sacks. As a junior, he started all but one game at left defensive end, recording 57 tackles, 12 tackles for loss and 8 sacks, 2 forced fumbles and one fumble recovery. He had 9 tackles, 2 sacks and one pass defensed against Indiana University. He finished the season with 7 tackles, one sack and 2 forced fumbles in the Aloha Bowl against the University of Washington. He missed his senior season because of a sprained right ankle injury, although it has been speculated that it was not the real reason.
Underwood was selected by the Minnesota Vikings in the first round of the 1999 NFL Draft, after his stock rose with his pre-draft workouts. On August 1, he signed a five-year, $5.3 million contract with a $1.7 million bonus. He walked out of training camp the next day on August 2, after the first practice and never returned. On August 13, he was waived and forfeited a $1.75 million bonus saying he could not resolve the conflict between playing football and serving his Christian faith. Although he eventually returned, he was released later that month and had to give back his signing bonus to the Vikings.
Miami Dolphins
On August 16, 1999, Underwood was claimed off waivers by the Miami Dolphins as 23 teams passed on him. He was signed for $395,000, played in only one preseason game before injuring his shoulder and also showing a lack of focus on football. Multiple times during team meetings, Underwood was found not taking notes, but instead writing about the apocalypse. He only played in the last preseason game against the Green Bay Packers, suffering a dislocated left shoulder. Although he made the team, he was deactivated for the first 2 games because of his injury. In September, Underwood was arrested by police for failure to pay child support for his 17-month-old twins. Following the team's bye week, he was placed on the reserve/non-football injury list on September 28. Underwood later spent two months in protective care and was diagnosed with bipolar disorder. After he escaped from a psychiatric care facility, he was released by the Dolphins on December 17.
Dallas Cowboys
On March 10, 2000, he signed a two-year contract with the Dallas Cowboys, who took a chance on him because of the earlier success the team had with Alonzo Spellman who also suffered from bipolar disorder. He was moved from defensive end to defensive tackle and was a backup player. He collected 23 tackles, 4 sacks and 14 quarterback pressures. In January 2001, he tried to kill himself for the second time by running into traffic twice on a busy suburban highway. During the season he appeared in 4 games, making 3 tackles, 2 quarterback pressures and one pass defensed. He was released in October after he missed practices and was admitted to a psychiatric hospital.
On May 24, 2005, he resurfaced in the Canadian Football League with the Ottawa Renegades, after four years out of football. However, he was cut during the preseason on June 13.
Struggles with bipolar disorder
Starting in 2002, he served stints in the Dallas County Jail for aggravated robbery, assault on public servant, and evading arrest. He spent his time in a closed custody cell. In 2007, Underwood entered the Philadelphia Industrial Correctional Center, and left in February 2011.
Personal life
A few months after Underwood was enrolled into Michigan State University, his father died from leukemia at the age of 47. In 2007, Charles Robinson of Yahoo! Sports listed Underwood as one of the worst first-round picks since the AFL-NFL merger. According to the article, Underwood missed most of his senior year, and his coaches at Michigan State warned NFL scouts that he was not mentally stable enough to play in the NFL. In Robinson's view, by ignoring these warnings the Vikings made "arguably the dumbest pick ever made in the first round." In a September 28, 2010 article Yahoo Sports noted Underwood's mental health issues as a case in point in regard to the NFL falling short in helping players who suffer from various mental illnesses that are in no small part connected to the pressures of the job of an NFL athlete. The 2010 article also pointed out that "Underwood was tormented by visions of the apocalypse. He used to write notes discussing the end of the world on pieces of paper the size of postage stamps. When he was in a normal state, he could be engaging in conversation. He was funny and intelligent. He also exuded physical confidence and had extraordinary talent."
