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Crosby has intermittently been involved in notable golf events since his retirement as a full-time touring professional. He regained his amateur status in 1994, initially in order to play in the AT&T Pebble Beach National Pro-Am, the tournament founded by his father. In 2007 he played in the Porter Cup, the site of one of his greatest triumphs as a junior golfer. He did not do well this time though, finishing in last place by five shots. He also attempted to qualify for the 2007 U.S Amateur. The event was held at San Francisco's Olympic Club for the first time since his 1981 victory. Crosby captained the 2019 Walker Cup team which defeated the Great Britain & Ireland team 15.5–10.5. He will return as captain in 2021.

Crosby would quickly retire as a touring professional but would work as a golf industry executive for the remainder of his career. In 1988 he became president of the Tony Penna Golf Company, an equipment manufacturer, where he worked for 10 years. He then worked at Orlimar for 4 years, working as an executive at direct marketing. Since his experience at Orlimar he formed his own company to pursue high-end real estate and golf developments. He is also currently trying to market his dad's name more, whose "brand" he feels is neglected compared to other stars of the era.

After graduating from college, Crosby turned professional in 1984. He failed to gain a place on the PGA Tour. In the 1980s the PGA Tour did not have a developmental tour so many young golfers in Crosby's situation played overseas. Crosby decided to play in Europe, qualifying for the European Tour before the 1985 season. He played full-time in Europe from 1985 to 1987. His best year was in 1985. He recorded a third place finish at the Portuguese Open, his only top-10 of the season. He would finish 87th on the Order of Merit and kept his card. The 1986 season was more of a struggle as he did not record any top-10s and missed the majority of cuts. He finished 115th on the Order of Merit and barely kept his card. In addition, he played five events on the PGA Tour that season, playing on sponsor's exemptions, but missed the cut in all of them. The 1987 season was Crosby's final season in Europe. He missed the cut in 14 of his 18 events and finished 158th on the Order of Merit, not keeping his card. His good play at the 1985 Portuguese Open would turn out to be the only top-10 of his European Tour career.

Crosby attended the University of Miami and played for the golf team. During college he qualified for the 1981 U.S. Amateur held at The Olympic Club in San Francisco, not far from where he grew up. He shockingly won the event; at the age of 19 he was the 3rd youngest winner ever. In addition to this youth, Crosby was not considered a uniquely talented amateur golfer. The legendary golf writer Herbert Warren Wind wrote in The New Yorker, "His swing was so unimpressive that most observers felt there had to be at least a thousand better amateur golfers in the country." He was usually not even the top golfer on his college's golf team, occasionally ranking 3rd- or 4th-best. Crosby defeated future PGA Tour pro Willie Wood in the semifinal and then 24-year-old engineer Brian Lindley in the final. The win qualified him for the 1982 U.S. Open, again held at another local northern California course, Pebble Beach. Crosby shot an opening round 77 and then quadrupled-bogeyed the par-5 14th hole on Friday putting him in danger of missing the cut. However, he shot −1 for the rest of the round to make the cut by two. He would shoot 76-77 on the weekend to finish at 303 (+15) and in solo 59th place. He was low amateur, besting future PGA Tour pro Corey Pavin by a shot. Also in 1982 Crosby won the Porter Cup, an elite medal-play event for amateurs. Most recent champions of the event – like Ben Crenshaw, John Cook, and Scott Simpson – had gone on to win on the PGA Tour, so the victory certainly boded well for Crosby. He also played on the victorious 1982 Eisenhower Trophy and 1983 Walker Cup teams.

Crosby performed with his father, mother, brother, and sister in several Christmas television shows and at the London Palladium in 1976. He starred along with the rest of his family in the 1970 television musical Goldilocks. Crosby stated that he was embarrassed to perform in the Christmas specials as he was not a natural performer.

Nathaniel Patrick Crosby (born October 29, 1961) is an American golfer. He won the 1981 U.S. Amateur and played on the winning 1982 Eisenhower Trophy and 1983 Walker Cup teams. He turned professional but had little success and was later reinstated as an amateur. He is the seventh child and sixth son of Bing Crosby.