A native of Boston, Pearl attended Sharon High School in Sharon, Massachusetts and is a 1982 graduate of Boston College, where he served as the manager of the men's basketball team. He and his ex-wife, Kimberly, have two daughters, Jacqui and Leah, and two sons, Steven, who is on the Tennessee basketball team, and Michael.

Before coming to Tennessee, Pearl was the head coach at Milwaukee and, prior to that, at Southern Indiana, where he won a Division II national championship. He also served as an assistant coach at the University of Iowa under then-head coach Tom Davis.

Among his accolades, Pearl is the second-fastest NCAA coach to reach 300 victories, and needed only 382 games to reach this mark (Roy Williams, the current coach at University of North Carolina at Chapel Hill, needed 370 games at the University of Kansas to reach this milestone). It should be noted, however, that all of Williams' victories came at the Division I level, whereas a portion of Pearl's victories came in Division II, and contributed to his rise to the Division I ranks.

Against division rival Kentucky and in-state rival Vanderbilt, Pearl chooses to wear a brightly colored orange jacket in honor of the late UT coach, Ray Mears. To show the importance of the game, Pearl wore the jacket during the 2009 SEC Men's Tournament Final.

During the 1988-89 basketball season, Pearl, then an assistant coach at the University of Iowa, was at the center of a recruiting scandal involving the University of Illinois at Urbana-Champaign. Both Illinois and Iowa were recruiting Deon Thomas, a top high school player from Chicago. Pearl lost this recruiting battle when Thomas committed to Illinois. Thereafter, Pearl called the high school student and recorded a phone conversation with Thomas. During the conversation, Pearl asked Thomas if he had been offered an SUV and cash by Illinois assistant coach Jimmy Collins, and Thomas indicated he had. Pearl then turned over copies of the tapes to the NCAA, accompanied by a memo describing the events. During the subsequent NCAA investigation, Thomas denied the allegations and said the story was false; a lie detector test supported Thomas' claim. The NCAA did not find Illinois guilty of any wrongdoing relating to Thomas' recruitment, finding that the proof provided was not "credible, persuasive and of a kind on which reasonably prudent persons rely in the conduct of serious affairs." However, since the investigation uncovered other violations, including Illinois' third major violation in six years, the NCAA cited Illinois with a "lack of institutional control" charge and implemented several recruiting restrictions and a one-year post-season ban. The event led to a "blackballing" by many coaches in D–I, and even led ESPN commentator Dick Vitale to call Pearl's actions "career suicide" during a telecast.

When Pearl and Collins were both head coaches for four years in the Horizon League, the two men never engaged in the traditional postgame handshake, reportedly due to lingering feelings over the incident. When Thomas was asked about forgiving Pearl in a 2005 interview, he was quoted as saying "It's hard to forgive a snake." Thomas went on to play basketball at the University of Illinois, becoming its all-time leading scorer.

Pearl picked up a Screaming Eagles team at USI in 1992 that had won just 10 games in the previous season. Pearl posted a 22–7 record in his first season, and led the Eagles to nine straight NCAA D-II tournaments in addition to winning four Great Lakes Valley Conference titles.

In 1994, USI finished with a 28–4 record en route to a loss in the D-II championship game; in 1995, the Eagles won 29 games and claimed the D–II championship. A team from the GLVC played for the National Championship every year after his first season at USI. Pearl was named the NABC Division II coach of the year after his national championship. He left USI with a 231–46 record over nine years.

Pearl took over as head coach of the Milwaukee Panthers men's basketball team in 2001. In just four seasons, he compiled 86 wins (including a school-record 26 in 2005, and a new Horizon League record for winning percentage) and led Milwaukee to their first NCAA tournament appearances in 2003 and 2005. Pearl led them to the Horizon League tournament title in both of those years. He also led the school to its first ever NIT bid, as well as its first-ever NCAA D–I postseason victory, in 2004. Milwaukee's 2005 NCAA Tournament run capped the best season in school history, as the Panthers won both the regular season and conference tournament titles, defeating rival Butler University in the championship game. Using an intense full-court press, the Panthers scored two upsets in three days over Alabama and Boston College en route to the Sweet Sixteen, where they fell to eventual national runner-up University of Illinois. The Panthers finished their season 26–6 and were ranked in the coaches poll at the end of the season for the first time ever (# 23). Pearl left UWM after the 2005 season, his fourth, as the Horizon League's leader in all-time winning percentage (51–13, 79.7%).

On March 28, 2005, Pearl was named as the new head coach at Tennessee, succeeding Buzz Peterson. Tyler Smith had signed with the Vols under Peterson, but decided not to attend Tennessee.Jaamont Gordon went to conference rival Mississippi State. Smith opted for a season of prep school before heading to Iowa, though later transferred to Tennessee and became a starter. Pearl stirred up more controversy when he released Matthew Dotson from his scholarship.