BY STEVE SOLLOWAY

Maine Sunday Telegram

His shoulders sagged as he walked past the basketball court. The weight of 28 months of planning and thousands of decisions seemed to be getting Jon Jennings down.

"The electric air pump quit," he said quietly, turning to look back at all the souvenir Maine Red Claws basketballs that needed to be inflated. It was going to take a lot of time and elbow grease to pump up the basketballs by hand.

Last Monday's moment in history was about 90 minutes away. The Red Claws were about to play their very first game at the Augusta Civic Center. Like a Broadway producer, Jennings had taken his production on the road for a tryout performance before Opening Night at the Portland Expo on Friday.

Jennings is the president and general manager of the team and an invested partner in Maine Basketball, LLC. He is 47 years old and has also worked as a White House Fellow during the Bill Clinton Administration, taught a class on the American presidency at Stonehill College, was known as the "Sock Guy" in Sen. Ted Kennedy's office and organized the party to end all going-away parties for President Clinton on the day George W. Bush was inaugurated.

That's just scratching Jennings' résumé. When you cut through the titles and job descriptions you reach the boy with the dream.

Member of the family

Back in Augusta, he looked again at the basketballs that had no bounce.

Jennings came to Portland in the summer of 2007. He had questions and he wanted answers and opinions. The NBA Development League had teams in small cities west of the Mississippi River. Maybe it was time to expand into the Northeast.

It was time for Jennings, an apprentice to Bobby Knight at Indiana University, George Irvine and Donnie Walsh with the Indianapolis Pacers and Red Auerbach and K.C. Jones with the Boston Celtics. He ran for the U.S. Congress in his home state of Indiana back in 2004 but lost to a six-term incumbent in what state pundits call the "Bloody 8th District."

Jennings raised $1 million more than his Republican opponent and had Larry Bird by his side on the campaign trail. He had also been away from Indiana for too long. He got 47 percent of the vote.

Before he died in 2006, Auerbach, the legendary coach and patriarch of the Boston Celtics, called Jennings. OK, you've got that out of your system. Now come back to your family.

Enthusiastic

Jennings brought K.C. Jones, when he visited Bill Ryan Sr., chairman of the board of TD Bank Inc. in 2007.

"I was mesmerized by K.C. Jones," says Ryan, of the man who coached Bird, Robert Parish, Kevin McHale and so many other Celtics greats. Ryan was also impressed with Jennings. "He was very sincere, very thorough. They had a study of minor league basketball. He told me how much he really wanted the basketball project to incorporate the community. As a banker and businessman I've heard a lot of proposals and this one was complete."

Ryan and his son, Bill Jr., signed on to the ownership group. They have the largest stakes.

Jennings asked Bill Troubh to accompany him in his meeting with Joe Gray, Portland's City Manager. Troubh had worked with Dan Burke to present the proposal to bring the Sea Dogs to Hadlock Field. That Jennings had enlisted Troubh for the initial talks regarding use of the Portland Expo wasn't lost on Gray.

Jennings' determined enthusiasm was noted, too.

"I was always fanatically devoted to being the best," says Jennings, sitting in his Maine Red Claws office. "I was the family freak show when I was a little boy. I could recite the names of all the presidents when people came to our house. When I was finished, my mother would say, 'That's nice, Jon. Now go back to bed.'"

A mature young man

Alice Jennings was a single mother, raising Jon and his little sister on paychecks from the local Alcoa plant in Richmond, Ind.

"My mother worked the third shift. She ran a machine that printed bottle caps. Then she'd come home and get me and my sister ready for school. I was the first in my family to graduate from high school."

He remembers the pictures of Mary, Joseph, and Jesus on the mantle. Joining the Holy Family was a small portrait of a handsome, smiling man. "For years I didn't know who it was or why he had such a special place on our mantle. Then I found out it was President (John F.) Kennedy."

Jennings' father left the family early in Jon's life. Jennings would devour biographies of men like Thomas Jefferson and Winston Churchill. "I identified with individuals who overcame obstacles when they young."

His fourth-grade teacher was Ken Clarke, Jennings' first male teacher at Parkview Elementary School. "Jon's father was gone," said Clarke from his home in Richmond, Ind. "I think I became the man in his life. Jon was such a great kid. He was already mature. He had all these questions."

Clarke played on Richmond High's 1942 state championship basketball team. He coached basketball at the elementary school, the only time Jennings played on a team. Jennings did play on the high school football team. On a Mountain Claws Q&A, Jennings is asked to list his most notable athletic achievement.

"What makes you think I had one."

Soon after Jennings graduated from Richmond he did something Clarke will never forget. "He endowed a $500 scholarship in my name. Who does things like that?"

"It was after I went to work for the Pacers," says Jennings. "Being a guy, you don't call your teacher up and say thank you. My way was to establish a scholarship for any kid going into education."

He ran for president of the Student Congress at Richmond High and won. "As part of my platform, I promised a trip to Washington for everyone who voted for me," says Jennings, with that small grin that has become familiar. "About a hundred of us went to Ronald Reagan's first inauguration."

It was Jennings' first trip to Washington. He had a general idea where he was going, but no real directions. He ended up with the tickets and got his classmates to the inauguration.

That's Jennings. Make a plan, follow it, open doors and enjoy. Find common ground with those you meet and bring sincerity, humor and insight.

Known to many

Simon Brown, a Red Claws intern and a senior sports management major at the University of Southern Maine, interviewed Jennings for a class paper. In a way, says Brown, the experience was like interviewing the Leonardo DiCaprio character in the 2002 movie "Catch Me If You Can," which was based on the true story of an imposter.

Except there's nothing pretend about Jennings. Except on Halloween night this fall when he and his 6-year-old daughter, Abigail, went to the home of Sen. Olympia Snowe and her husband, Jock McKernan, the former governor. The senator answered the door and then called to her husband. "Jock, come out here. You'll never guess who the Tin Man is."

No one knows who will walk through the doors to the Red Claws' office next. On the first day of training camp two weeks ago, Jennings introduced the team to Thurgood Marshall, Jr., son of the first black U.S. Supreme Court Justice and a friend to Jennings.

At Indiana University, basketball players Dan Dakick and Rick Rowray invite Jennings to a pizza party at Coach Knight's house. Soon, Jennings is working for Knight.

Jennings is hired by K.C. Jones, meets Auerbach and becomes his racquetball opponent. He brings tapes of Auerbach's favorite TV shows, "Hawaii Five-O" and "Magnum P.I.," to Red's office.

Bird welcomes Jennings to the Celtics family as a fellow Hoosier. "Actually, he called me hillbilly which was pretty funny," says Jennings. "Because he was one. We did grow up in similar circumstances."

And there's Reggie Lewis, the Northeastern star who becomes the hometown Celtics favorite, dies prematurely from a heart attack. Jennings stays close to Lewis' widow and, with Lenny Zakim, establishes Team Harmony in Boston's poorer neighborhoods. Zakim dies and today a bridge leading into Boston bears his name while Jennings still works for those in need.

Jennings meets Sen. Kennedy, who mentions how comfortable NBA socks are. Soon, Kennedy has a supply. Jennings attends Harvard's Kennedy School of Government for his master's in Public Administration.

Rick Pitino arrives to coach the Celtics and fires Jennings and the other assistants who were working for Pitino's predecessor, Chris Ford. Jennings heads to Washington in 1997 to work several jobs in the Clinton White House, including one as liaison to the President's Initiative on Race. Two years later Jennings is at the Department of Justice, working under Janet Reno as assistant attorney general acting as primary liaison to Congress.

In Jennings' office, enlarged photos march across the walls -- Jennings with Pope John Paul II, Jennings presenting Nelson Mandela with a Celtics uniform top with Mandela's name on the back. Jennings with Ted Kennedy.

By the door is a picture drawn in crayon by his daughter of her and Jennings. She has pigtails and is riding her bike. Jon is next to her and very svelte. "Of all the pictures in his office, that, by far, means the most to me."

He asked her mother to their eighth-grade prom back in Richmond, Ind. He thinks the phone conversation lasted 90 seconds. He was afraid Amy Elsea would say no after she said yes.

"I had the biggest crush on her and I think she thought I was the biggest loser."

They didn't date again through high school. While he went on to Indiana University, she went to Purdue. In 2001, Jennings saw her name and e-mail address on the registration list for their 20th high school reunion. She wasn't going to attend. Her twin sister talked her into it.

Jon and Amy married seven years ago on Martha's Vineyard. Ken Clarke and his wife drove from Indiana to be there.

Dream fulfilled

Last Monday night, the electric air pump, on loan from the University of Maine at Augusta, cooled and began to work again. The game with the Springfield Armor, coached by former Celtics guard Dee Brown, started. Jennings sat next to the Red Claws bench.

By halftime, the crowd was responding with cheers and applause to the Red Claws play. Jennings got emotional. The home opener in Portland was days away and an inaugural season needs to be completed. But his plan was working, his dream coming true. Nearby, Bill Ryan Sr. clapped his hands.

"Jon is not unique," said Ryan. "He is special."