The 1999 season was a disaster for Leaf. In June, he decided to play in charity golf tournaments rather than attend a voluntary
mini-camp. Then on July 23 during his pre-camp physical, doctors discovered a tear in his right labrum.
On August 19, Leaf tried to confront a heckler who called him a loser and compared the injured quarterback to another well
known bust, Heath Shuler. Leaf had to be restrained by two coaches and escorted off the field. This embarrassing incident
was also caught on tape and played in the media ad nausea. That episode, along with the shoulder injury prompted the Chargers
to place Leaf on injured reserve wiping out his sophomore season.
Leaf continued to make headlines in 1999 despite not being on the active roster. In November he got into a profanity laced
shouting match with general manager Bobby Beathard after refusing to complete a workout. For that he was fined a weeks pay
– $73,500 – and suspended four weeks without pay. During the suspension he was seen playing flag football.
After a relatively quiet off season that included thoughts of retirement and a visit to a shaman, Leaf returned to action
in 2000. Basically out of desperation, the Chargers named him their opening day starter. He didn't keep the job for long.
After posting a 33.4 QB rating in two losses, Leaf was benched in favor of Moses Moreno.
Moreno however, was quickly injured and Leaf was thrust back into action. In Week 4 against Seattle he injured his wrist throwing
an interception. That injury would keep him out for eight weeks. While he deemed himself "unfit" to play football, the injury
didn't stop Leaf from hitting the golf course.
Leaf returned to action in Week 11 and played his best game as a pro in Week 12. In a 38-37 loss to Denver, he completed 13
of 27 passes for 311 yards, 3 TDs, and 1 interception. The following week, he guided the team to their only victory of the
season, a 17-16 squeaker over Kansas City. Leaf threw 2 TD passes and 2 interceptions in the victory.
The underachieving signal caller started the Chargers final four games, all losses and took off to get married. On February
28, 2001, while he was on his honeymoon in Tahiti, the Chargers waived the disgruntled signal caller. He was picked up the
next day by Tampa Bay, who paid the $100 waiver fee for his rights.