The longest drive in Tiger Woods' career is actually the longest drive of the millennium on the PGA Tour.
The longest drive of Woods' career came at the 2002 Mercedes Championships (now the Tournament of Champions) on the Plantation Course at the Kapalua Resort in Hawaii. On the par-5 18th hole of the third round of the tournament, Woods hit a 498-yard drive to the massive downhill, downwind (that day) hole. That drive is the longest drive in the history of the PGA Tour, as measured by ShotLink.
Believe it or not, with that kind of length, all kinds of golfers hit mammoth drives that day. In fact, 10 of the 11 longest drives in PGA Tour history during the ShotLink era came on that hole on that day. Woods finished T-10 that week in the winners-only event, behind winner Sergio Garcia.
Earlier in his career, Tiger Woods was one of the two or three longest drivers in golf. Now that he's in his 40s, Woods is unlikely to top his longest drive during his career.
In Woods' career, he has six 400-yard drives on the PGA Tour, but that one at Kapalua was Tiger Woods' longest drive by a long shot.