Leonard's wins on the
PGA Tour included one of golf's four
majors, the
1997 Open Championship, as well as the
1998 Players Championship. He ranked in the top 10 of the
Official World Golf Ranking for 24 weeks in 1998 and 1999. Leonard also had opportunities to win other major championships, notably at the
1999 Open Championship and the
2004 PGA Championship; in both instances he fell into a playoff with a bogey on the 72nd hole. At the
1997 PGA Championship, Leonard was tied with
Davis Love III for the 54-hole lead. Love shot a final round 66 to win by five shots over Leonard, who finished solo second. Leonard was ahead by three shots at the 54-hole mark of the
2002 PGA Championship before shooting a final round 77 and finishing tied for fourth. Leonard qualified for the United States
Ryder Cup team in
1997,
1999, and
2008. In the 1999 event, Leonard made a putt for birdie on the 17th hole to complete a remarkable comeback by the U.S. team on the final day. The victory was somewhat marred by the celebration following Leonard's putt, when other U.S. players, their wives, and a few fans ran onto the green even though Leonard's opponent,
José María Olazábal, still had an opportunity to match Leonard on the hole.
Broadcasting career In 2015, Leonard moved to
Aspen, Colorado, which is not conducive to the year-round practice of golf and began to transition to a career as a golf announcer. After using his career money list exemption for the 2015–16 season and failing to make the FedEx Cup, Leonard played the 2016–17 season with past champion status. He played in only 16 tournaments that year, his best finish being a tie for 16th at the Northern Trust Open. In 2017, he played in only one tournament, the Texas Open, where he finished in 58th. In 2020, he assumed an elevated role on Golf Central "Live From" as an analyst on the program's primetime shows. Leonard made his PGA Tour Champions debut at the 2022
Senior Players Championship where he finished in 61st place. In 2023, his first full season on the tour, he carded a course record score of 62 in the first round of the
American Family Insurance Championship at University Ridge Golf Course in Madison, Wisconsin and finished tied for 4th, his best finish since 2014. Later that season he finished in a tie for 1st at the
PURE Insurance Championship, but lost the playoff to
Thongchai Jaidee on the 4th sudden-death hole. It was his best finish since winning the 2008 St. Jude Open. In February 2025, he won his first senior event, the
Chubb Classic. ==Amateur wins==