Craig is the second of four sons of Marion and John Elroy McCaw. McCaw's Father was a broadcasting magnate and owner of Gotham Broadcasting Corporation. WINS which became one of the first stations to play rock and roll. Alan Freed was the earliest famous personality disc jockey on the show. McCaw's Father was in the Business of buying and selling TV and radio stations, which brought in wealth but also incurred significant debts. Elroy entered the cable television Business in the 1960s, and his four sons worked as linemen and door-to-door salesmen.
When the FCC held a lottery for cellular licenses in the early 1980s, many ordinary Americans got rich by winning the right to establish cellular systems in cities across America. In addition to entering the lottery himself, McCaw approached many other lottery winners and bought their cellular rights, which were already considered to be undervalued. Using the same tactic he'd used in cable TV, McCaw financed an aggressive cellular expansion by borrowing against and selling shares in the cable operation. Through continued borrowing and smart management of only the most useful licenses, this wireless land grab put McCaw's operation in the position of a competitive nationwide cellular carrier before the incumbent landline telephone industry took serious notice of the field.
After acquiring MCI's cellular wing in 1986, the McCaw brothers sold the cable company to Cooke Cablevision (now part of Comcast). The combined cellular operation was a significant player in the field. In 1990, McCaw was the highest paid CEO in the US.
McCaw was a founding donor and underwriter of the Free Willy Foundation (along with Warner Brothers Studios) from 1993 to 2002, with an original $2m donation. The foundation was formed to re-release Keiko the Killer Whale into the wild. It was later known as the Free Willy-Keiko Foundation.
In 1994, McCaw and Bill Gates teamed up to form Teledesic, with an ambitious plan to form a broadband satellite communications system with nearly 300 low earth orbit satellites. In 2002, Teledesic halted satellite production; and in 2003, it sold its spectrum licenses.
Following the sale of McCaw Cellular, McCaw took interest in Nextel, a then-floundering wireless carrier. By April 1995 McCaw gained effective control of the company contributing, along with his brothers, $1.1 billion over time. Within four years Nextel grew significantly to become a challenging wireless competitor, servicing 3.6 million customers throughout the U.S. and ten of the largest international markets. In 1999 McCaw formed Nextel Partners, Inc. which was later acquired by Sprint Nextel, Inc., for $6.5 billion in 2006, following a $36 billion merger between Nextel and the Sprint Corporation in 2005.
Later that same year, McCaw founded NEXTLINK Communications, planning to enter the broadband and internet Service provider market. In 2000, the company merged with Concentric Network and was renamed XO Communications. The company filed for bankruptcy protection in 2002.
In August 2004, McCaw founded Clearwire Corporation, a provider of wireless broadband Internet Service. The company's U.S. broadband network is deployed in markets ranging from major metropolitan areas to small, rural communities.
At the end of 2007, Clearwire offered Service in 46 markets in the U.S. as well as four markets in Europe.
In November 2008, Clearwire completed a landmark transaction with Sprint combining their next-generation wireless broadband businesses into a new wireless communications company, which retained the name Clearwire. With the closing, Sprint contributed all of its 2.5 GHz spectrum and its WiMAX-related assets, including its XOHM Business, to Clearwire. In addition, Clearwire received a $3.2 billion cash investment from Comcast, Intel, Time Warner Cable, Google and Bright House Networks.
In January 2009, Clearwire launched its first 4G mobile WiMAX network in Portland, Oregon, making it only the second city after Baltimore to offer a high-speed network at true broadband speeds. By the end of 2010, the company had expanded its 4G network to 71 markets in the U.S. covering more than 110 million people.
McCaw, who served as Chairman of Clearwire until December 31, 2010, once said to an interviewer, "Filling a need that others aren't addressing has always been a focus of the companies that I have been involved with."
McCaw is a significant car collector, and once amassed a collection of 400 cars with his brother, Bruce. In 2012 McCaw paid $38.1 million for a 1962 Ferrari 250 GTO, setting a new record for the most expensive car ever sold. The 250 GTO was originally built for Stirling Moss, who never raced the car. It was driven at the 1962 24 Hours of Le Mans by Innes Ireland and Masten Gregory.
As of 2016 Craig McCaw is no longer on the Forbes 400 List of Wealthiest Americans.