Donaldson's first appearance on Survivor was in the second season, Survivor: The Australian Outback. After being placed on the tribe Ogakor, he quickly formed a bond with fellow castaways Amber Brkich, Jerri Manthey, and Mitchell Olson. However, he also acted as the swing vote between the alliance between Olson, Manthey, and Brkich and the alliance between Tina Wesson and Keith Famie. Donaldson ended up siding with Wesson and Famie in the decision to eliminate Olson. After the tribes merged, Donaldson joined the rest of Ogakor in systematically eliminating the former members of the rival tribe, Kucha. Near the end of the competition, he won the final immunity challenge, over former allies Wesson and Famie. As a result, he was given the choice of whom to face in the jury vote. He had formed an alliance with Wesson early in the show and stated that he wanted to see that through. He also said that he did not want Famie to have a shot at winning the title. In the end, Donaldson cast his vote to eliminate Famie, who was generally disliked, and who Donaldson perceived as less deserving to win the title of Sole Survivor, should Donaldson not win himself. Ultimately, Donaldson finished in second place, with Wesson winning in a 4–3 vote, earning the votes from Brkich along with former Kucha members Nick Brown and Rodger Bingham.
He participated in Survivor: All Stars, six seasons later. He was on the Mogo Mogo tribe and was the fifth person voted out (but seventh overall to leave the game due to two contestants voluntarily leaving). At Survivor: America's Tribal Council, Donaldson was voted by an online poll as the "sexiest male castaway" out of all players from the first eight seasons.
Donaldson returned to play for a third time in the twentieth season, Survivor: Heroes vs. Villains, and was placed on the Heroes tribe. He quickly became an outsider, after forming an alliance with ex-Survivor: Palau players Tom Westman and Stephenie LaGrossa, who were both eliminated within the tribe's first four tribal councils. At the tribe's fifth elimination, Donaldson was targeted as an outsider, but was ultimately spared by the tribe, instead voting out the injured James Clement. He and the rest of the Heroes tribe won the last three immunity challenges before the merge. As a result, both tribes entered the merge with five members each. After "villain" Parvati Shallow gave hidden immunity idols to allies Sandra Diaz-Twine and Donaldson's Australian Outback tribemate Jerri Manthey; Donaldson's ally and "hero" J.T. Thomas was eliminated, giving the former Villains tribe members the advantage in numbers. After Thomas's elimination, all four remaining Heroes were eliminated within the next five tribal councils, with Donaldson being the last "hero" remaining in the final episode. Ultimately, he was voted out on Day 37 and became the eighth jury member, casting his jury vote for the season's winner, Diaz-Twine over "villains" Shallow and Russell Hantz.
Donaldson also hosts the new spin off of Top Shot, called Top Guns, which premiered on H2 February 15, 2012, and features firearm instructors and former Top Shot competitors who test firearms throughout history.