He made the first ascents of some of the hardest sport climbing routes in the U.S., including Kryptoniteat5.14d (9a) in 1999, and Flex Luthorat9a+ (5.15a) in 2003, both at the Fortress of Solitude in Colorado. In January 2015, Caldwell and Kevin Jorgeson over 19-days made the first free ascent of The Dawn Wall on El Capitan, which was the first-ever big wall free climb at 9a (5.14d) in history.[2]
Caldwell and three fellow climbers Beth Rodden, John Dickey, and Jason 'Singer' Smith were held hostage for six days by rebels in Kyrgyzstan in August 2000. Caldwell pushed one of the kidnappers off a cliff, and subsequently escaped to government soldiers.[7][8] A few weeks later they learned that the man had survived the fall.[9] A book about their ordeal, Over the Edge: The True Story of Four American Climbers' Kidnap and Escape in the Mountains of Central Asia was written by Greg Child.[10] A follow-up article, "Back from the Edge", was published in Outside magazine the following year.[11] Caldwell gave a filmed lecture "How Becoming a Hostage and Losing a Finger Made Him a Better Climber".[12] The Kyrgyzstan incident is included in the 2017 film The Dawn Wall.
Caldwell accidentally sawed off much of his left index finger with a table saw in 2001. Doctors were able to reattach the severed portion, but Caldwell decided he did not want the useless finger, which doctors said would never heal fully and he would never be able to use to climb with again, and the damaged part of the finger was later permanently removed.[13][14] After three surgeries, and two blood transfusion, Caldwell was told by the doctor "You better start thinking about what else you want to do with your life." Facing the fear of never climbing again and losing something he loved so much, became Caldwell's greatest strength.[15]
He made the first ascents of some of the United States hardest sport routes including Flex Luthor in 2003 at the Fortress of Solitude, in Colorado, which remained unrepeated for 18 years, before getting its first repeat by Matty Hong in October 2021, who suggested a possible grade 5.15b (9b), but was regraded to 9a+ (5.15a) by Jonathan Siegrist in 2022.[16]
In May 2004, he completed the first free ascent (FFA) of Dihedral Wall. In 2005, he and Beth Rodden—swapping leads—made the third and fourth free ascents of The Nose. Two days later, on October 16, Caldwell free-climbed The Nose in less than 12 hours. A few days later, Caldwell climbed The Nose in 11 hours, descended the East Ledges, and then climbed Freerider, topping out 12 hours later – the first ascent of two El Capitan free climbs in 24 hours. On El Capitan, Caldwell has also free-climbed: Lurking Fear, Muir Wall, West Buttress, Salathé, Zodiac, Magic Mushroom, The Dawn Wall, and New Dawn.[1]
In January 2015, Caldwell and Kevin Jorgeson completed the first free climb of The Dawn WallonEl Capitan in Yosemite National Park, after six years of planning and preparation.[17][18]
Their 19-day ascent of The Dawn Wall was the first-ever free climb of a big wall route at the grade of 9a (5.14d) in history.[2]
The ascent captured global attention and earned a nod from President Barack Obama, who said: "You remind us that anything is possible", and which was made into the 2017 climbing film, The Dawn Wall.[19]
The following year Czech climber Adam Ondra free climbed the Dawn Wall in 8 days.[20] Ondra praised Caldwell and Jorgeson saying, "Tommy and Kevin put so much effort into the climb and faced so many question marks and logistical problems that I cannot really compare my effort to theirs. I had it prepared, had all the knowledge. I knew it was possible".[21]
Caldwell was one of the climbers featured in the 2009 film Progression.[22] The film discussed his quest to climb The Dawn Wall, and it was after seeing the film that Jorgeson contacted Caldwell to join him in the effort.
The Dawn Wall, a documentary following Caldwell and Jorgeson on their free climb of The Dawn Wall, was released on September 19, 2018. The documentary was directed by Josh Lowell and Peter Mortimer.[23]
Caldwell appeared in the documentary Free Solo, released on September 28, 2018, about Alex Honnold's free solo ascent of Freerider on El Capitan in Yosemite National Park. In the documentary, Caldwell is seen working with Honnold to prepare for the climb and is interviewed about Honnold and rock climbing.[24]
Caldwell and Beth Rodden married in 2003, and subsequently divorced in 2010.[37] In 2010[3] he met photographer Rebecca Pietsch. They married in 2012. The couple have a son, Fitz, and a daughter, Ingrid Wilde,[38][39] and live in Estes Park, Colorado.[40][2]
