He was so miserable he asked his wife, Janice, if it would be OK for him to look for another line of work. Instead of asking him to show her the money, she supported his dream by waiting tables.
That decision was made easier after Green convinced fellow Wittenberg College graduate Bob Wagner to let him be his graduate assistant in 1995.
At the time, Wagner questioned Green's sanity, but after hiring Michael Carter to be his quarterbacks coach, he needed someone to be the G.A., so Green was it.
Green survived Wagner's firing to become University of Hawaii head coach Fred vonAppen's graduate assistant in 1996. Like Wagner, vonAppen wondered if Green was all there.
He soon discovered last fall that Green not only knew how to interpret criminal defense, but was pretty good on the offensive side of the football field as well.
So much so that, yesterday, vonAppen decided to hire Green as his receivers and tight ends coach. He replaces Walt Klinker, who, in two days, will leave Hawaii to become the University of Kansas offensive line assistant.
"Get the hell out of my office," Klinker jokingly said to Green after yesterday's announcement. "This is still my desk for a couple of more days."
Klinker's job of coaching the big uglies on offense shifts to the shoulders of Alima Afoa, who handled the offensive line at San Diego State during the Aztecs' 1986 Western Athletic Conference championship season.
That means Doug Semones will slide into Afoa's spot and coach the defensive line. VonAppen believes it's the final piece of the puzzle to his new-look staff.
The second-year coach has lost Klinker to Kansas, secondary coach Trent Miles to Fresno State and wide receivers assistant Ken Margerum to Menlo College.
He hired former National Football League player Mickey Pruitt to handle the secondary. VonAppen also landed Wally English, who will be the offensive coordinator. Guy Benjamin will handle quarterbacks and also coordinate the academic end of the equation.
"When you see something is broken, you'd better fix it, pal," VonAppen said yesterday. "We feel like these changes are for the good of the program.
"I'm very happy to keep Tim Green with us. I was afraid we might lose him. He has a fine football mind. I'm not sure why a lawyer wants to be a coach, but we're lucky to have him."
Green wore a wide smile most of the day. He was feeling a little corny, but after looking back on the last three years, who could blame him?
"Unbelievable," Green said. "Truly a dream come true. I'm ecstatic because it's an awesome opportunity for my wife and myself to coach in Division I football.
"Three years ago, I was working in a law firm and volunteering high school football. I had a great opportunity from Coach Wagner to get my foot in the door.
"I coached running backs the first year, helped Guy with the quarterbacks last year and learned a ton. Obviously,
Fred has given me a great opportunity."
It's also an opportunity for Semones to continue his odyssey and allow Afoa to return to a side of the field he knows and loves.
"It's a position I played in college (San Diego State)," Afoa said. "I also coached it at San Diego State, along with special teams and tight ends.
"I will help Tim with the tight ends. He'll handle the receiver phase and I'll handle the blocking. I'm excited about the switch."
Semones echoed that sentiment.
"It's great I'm going to the other side of the ball and learn some things from (UH defensive coordinator) Don Linsdey. My personality is more suited for defense.
"I was a defensive player. I was a defensive coordinator in high school before becoming a head coach. I've always been kind of a defensive guy first.
"I was fortunate to work on the offensive side of the ball last year with tight ends to learn that system. Now, I'm going to the defensive side to further my education.
"I'm still going to spearhead special teams, but there are going to be different units on both sides of the ball working on it. We will be improved on special teams next year, I guarantee it."
Semones will handle the three interior linemen in the new 3-4 look Hawaii will unveil next season. The top returnees up front are Ben Bright, Tony Tuioti, Ellie Kapihe and Bob Piggot.
As for Green, he's just glad to be the newest member of the club.
"I always loved football and I despised practicing law," Green said. "I asked my wife if it would be OK if I looked for a college coaching job.
"She saw how miserable I was and was excited when we got the opportunity to come here. She said let's go. When I found out on Monday, we just looked at each other. For us, it's unbelieveable how it all worked out."