Upon being recruited by Jim Tressel at Youngstown State in 1996, he failed to land the starting job at quarterback and transferred to Division II Tiffin University. He had no offers to play right after college. In fact, the last time he played professional football was for the now-defunct Memphis Xplorers in 2007. It was an Arena Football League developmental team.
So why is Whitfield, 34, in such high demand?
"He's as thorough and as passionate a guy as I've ever seen," Baltimore Ravens offensive coordinator Cam Cameron says. "People listen to him and what he says. It would be hard not to once you get to know him."
One of those is Luck, the presumed No. 1 selection in next week's NFL Draft. The former Stanford star will be Whitfield's second pupil in as many years to earn the top spot, joining the record-setting Newton. And before that, Whitfield put Roethlisberger through the rigors while he was suspended for the first four games of the 2010 season.
Luck has been hailed as one of the greatest quarterback prospects in history. At 6-foot-4, 234 pounds, he has prototypical size for the position and is very mobile. His IQ may be average for Stanford, but it's believed to be in the upper echelon for football. Luck's passing ability is among the best of his generation.
But it didn't mean NFL talent evaluators were without questions. Some wondered if he could make the necessary deep throws. Others debated whether his release was fast enough.
Whitfield -- along with Hall of Fame quarterback Warren Moon -- sought to address these concerns.
"We really just tried to keep him sharp," Moon said. "This guy doesn't really have a lot of weaknesses, that's why he's rated so high. He can do everything very well and some things exceptional."
Whitfield admitted he didn't try to change much of what made Luck so successful in college. The entire process lasted a little over a month, with the first two weeks taking place at the Home Depot Center in Los Angeles in preparation for the NFL Combine in late February. The final stretch at Stanford led to Luck's Pro Day on March 22.
Luck trained four days in a row before taking the fifth off and then started the routine again. Whitfield's sessions -- each lasting about three hours -- focused primarily on improving mechanics for deep passes. The duo also worked on keeping the ball a little higher so the release is quicker. Many drills centered on footwork.
Whitfield also had what he called "unconventional" methods, including the now-famous broom he used to chase Luck in front of NFL scouts.
"Me coming after you wearing golf shorts and aviator glasses isn't real scary for these guys who are 6-4, 6-5 and built like linebackers," Whitfield said. "That broom is an element of pressure and stress. If the testing methods are strange or if I have to walk around Home Depot to do it, so be it. I have to make sure that you know, 100 percent, these mechanics will survive out there in a game."
Players training with Whitfield have participated with eye patches. They've worked out in the Pacific Ocean. Bean bag activities have been used to improve hand-eye coordination and focus. Cameras have been attached to a quarterback's head so video could be watched later to see where their eyes were moving.
Whitfield gave former LSU quarterback Jarrett Lee two Chinese metal balls to continually roll around in his hand while they trained this offseason in San Diego. The balls were supposed to improve dexterity.
"I thought he was joking when he gave them to me. It actually really helped," Lee said. "He knows little things like that. It's kind of why they call him 'the quarterback guru.'"
Years ago, that wasn't a phrase even closely associated with Whitfield. But thanks to what he calls "an accident," that's changed.
Whitfield was born in Wichita, Kan., but grew up in Massillon, Ohio, a town known for its football obsession. Baby boys are given a miniature ball at birth. Paul Brown Tiger Stadium, where Massillon Washington High plays, seats nearly 20,000 people.
As a second grader, Whitfield got his first job in life: team water boy. It wasn't the position that attracted him, but rather the feeling of being on the field with his "biggest heroes."
He was soon promoted to the kid who grabs the tee after a kickoff. As a fifth and sixth grader, he caught passes from wide receivers at practice. "I still have never looked up to anybody as much as I did those Massillon players then," he says.
Whitfield's dream was to become the school's starting quarterback, and it happened as a senior. That 7-3 season in 1995 earned him honorable mention All-State and team MVP honors. He later committed to play at Youngstown State.
In 1996, Whitfield suited up for Tressel and the Penguins, but saw limited action on the field. In hopes of earning more playing time, he transferred to Tiffin University, a mere 132 miles down the road, where he subsequently became one of the top passers in school history.
Despite Whitfield's success on the Division II level, a shoulder injury hurt his chance to play on the next level. He became a graduate assistant at Iowa instead, and remained there for a year before heading to San Diego to continue training. He played from 2004 until 2007 in the Arena Football League before deciding to call it quits.
Whitfield considered law school as his next direction, but needed extra money on the side. He applied for a marketing job at a beer company, however "once I turned in the resume, [the interviewer] said she had another idea."
She had a son, a fifth-grader named Mike Hinkley, who wanted to improve as a quarterback. Whitfield began the sessions in June 2007 and went through the fall.
"As his [Pop Warner] season progressed, every week I got a call from another dad or coach that he had played against," Whitfield said. "It just snowballed from there."
While training young players in '07, he also spent the summer interning under Cameron with the San Diego Chargers. Whitfield charted all the quarterbacks, including now-Pro Bowler Philip Rivers, and put together in-depth reports for coaches.
It was then that Whitfield realized what he wanted to do the rest of his life.
Hunter Cantwell remembers the competitiveness.
The former Louisville quarterback began working with Whitfield in December 2009, shortly after his college career ended. The coach spent three months fine-tuning Cantwell's throwing motion, one that he said "looked like [New York Yankees pitcher] Andy Pettitte's."
When they weren't out on the field, the two squared off at other activities.
"He's extremely competitive," Cantwell said. "It could be playing cards or pickup basketball, George is giving you a hard time or some smack talk. Always making things interesting."
That extra intensity, Cantwell added, pushed the quarterback on a daily basis.
It was also seen recently from Luck, Lee, Oklahoma's Landry Jones, Virginia Tech's Logan Thomas, Clemson's Tajh Boyd and North Carolina State's Pete Thomas -- all players he's trained this offseason. Whitfield additionally worked with quarterbacks as young as middle school.
The particular player doesn't matter much to him. Whitfield claims he is just as excited seeing a high school quarterback earn his first scholarship compared to a college star going No. 1 overall in the NFL Draft.
No matter the age and accolades, he prides himself most on his honesty with players. When Whitfield first met Newton -- who just weeks earlier had led Auburn to a National Championship and won the Heisman Trophy -- the two had dinner right after Newton's flight landed in San Diego.
While waiting for food, both men traded six napkins apiece detailing fronts, defensive coverages, adjustments and blitz packages of Oregon, the opponent Auburn had faced in the title game. Whitfield then spoke about what Newton had to work on and his plan on how to accomplish it.
"Guys want to know what's wrong, and they want you to be honest with them," Whitfield said. "How succinctly can you get them back on track as a player or improve them? I think that's my strongest asset. If you can establish that trust and that type of bond, they'll go with you wherever."
Whitfield spends most mornings and early afternoons training an individual or group of quarterbacks. He'll devote additional hours each night to breaking down film of the earlier workout or picking the brain of friends in the industry.
Among those on his speed dial: head coaches Jim Harbaugh (San Francisco 49ers">49ers) and James Franklin (Vanderbilt) as well as quarterbacks coaches Geep Chryst (49ers) and Tom Herman (Ohio State).
Cameron said they speak every month, often at least once a week.
Typically, he added, Whitfield will call to talk about the industry or gain guidance on specific ways to develop a quarterback. The tables have recently turned.
"I've had seasoned quarterbacks that are calling me about George," Cameron said. "Pro Bowl caliber quarterbacks. I won't name names, but I recommend him every time. The word is finally out there."
At the moment, Whitfield is content with his current job status. He's had interest from both college and professional teams to coach, but enjoys having things at his own pace. Life in San Diego, with beautiful weather all year, suits him personally and his business.
However the most important reason, Whitfield admitted, is seeing young players reach their goals.
"The dynamic of getting a chance to be that guy in that corner for the boxers, it's special and I love it," he said. " I think I have the greatest job in the world."
On a warm April afternoon in San Diego, Whitfield walks to a nearby football field to meet with Austin, a 12-year-old from Orange County.
Just weeks removed from tutoring arguably the best quarterback in college football, Whitfield has similar drills planned for the middle schooler.
"He might only be five-foot, but he's sharp," Whitfield said. "We're going to work on throwing on the run to the left today. We'll see if we can get that down."
But it won't stop Whitfield from trying.