His 23 United States Tennis Association (USTA) Pro Circuit singles titles were the all-time record, as of November 2013.

Playing for the University of Miami in 1996–97, he was named National Collegiate Athletic Association (NCAA) Rookie of the Year, before he turned pro in 1997.

A high school valedictorian, Russell was one of few Association of Tennis Professionals (ATP) players in his time who had a college degree, having earned a B.S.

[2] In the fourth round of the 2001 French Open (his best run at a major) against defending and eventual champion Gustavo Kuerten (as well as the contemporary world No.

Other career highlights include a fourth-round showing at the 2007 Indian Wells Masters event, a semifinal appearance at the 2012 U.S. Men's Clay Court Championships, and wins against top-10 players Mardy Fish and Tomáš Berdych.

He has coached Frances Tiafoe, Ryan Harrison, Sam Querrey, Taylor Fritz and Mackenzie McDonald through USTA Player Development.

[1][3][4] He started playing tennis at age five with his father, George, who was formerly a member of the University of Michigan's Big Ten Conference 1965 championship team.

[2][10] He was one of the few Association of Tennis Professionals players while he played who had a college degree, having earned a Bachelor of Science in business administration from the University of Phoenix in January 2012.

[2] Russell reached the second round in singles and the quarterfinals in doubles with Kim at the 1995 Australian Open Junior Championships.

[2] He lost in the singles finals at the 1996 USTA National Boys' 18 Clay Court Championships to Bob Bryan.

[6] He was named 1997 NCAA Rookie of the Year and an All-American, and finished # 7 in collegiate rankings (and # 1 among freshmen), before he turned pro in 1997.

[14] A week before he was to go pro in 1997, while serving to Andre Agassi during a 1997 practice session in North Carolina he suffered a spiral fracture of the humerus bone in his right arm.

[2] He also won his first ATP match, defeating Hugo Armando in the first round of the U.S. Men's Clay Court Championships in Orlando, Florida.

[2] Russell won the singles and doubles, with Robert Kendrick, championships at the USTA Futures event in Mobile, Alabama.

[6] He spent four and a half months in rehab, and began taking courses at University of California, Berkeley by the internet.

[6] Two weeks later, in the first round of the 2007 Australian Open, Russell led former # 1 player Lleyton Hewitt two sets to love on center court before succumbing.

[6][19] In the 2007 Indian Wells Masters event, he made it to the final 16 players in a 96-player field, after upsetting 11th seed – and 12th-ranked – Tomáš Berdych in round 2 in straight sets.

But as sportswriter Greg Garber wrote in an ESPN article, after expenses, "In terms of net income, a minimum-wage worker at McDonald's did better financially than Russell did during the nine years before 2007.

He came through qualifying and beat top seed, world # 9 and compatriot Mardy Fish in straight sets on his way to a three-set loss to Juan Mónaco.

[23] Russell, as a lucky loser, made it to the quarterfinals of the 2013 U.S. National Indoor Tennis Championships, losing to Denis Istomin in straight sets.

[24] In November 2013, he won an ATP Challenger in Charlottesville by coming back from 0–5 in the final set against Canadian Peter Polansky for the win.

In 2015 at 36 years of age, Russell earned a spot representing premier American men's professional tennis at the Australian Open.

Annually, the Australian Open serves as the initial Grand Slam event in the (ITF) professional series.

Russell has coached Frances Tiafoe, Ryan Harrison, Sam Querrey, Taylor Fritz, Mackenzie McDonald and Tennys Sandgren on the ATP WorldTour through USTA Player Development.