In my memory, Kenny Anderson is the point guard who quarterbacked the best Celtics teams of my teenage years, the lefty who helped take Boston to the Eastern Conference finals, the precocious talent who never lived up to his potential, and the disappointment who never, ever should have been traded for Chauncey Billups.

Now, according to the South Florida Sun Sentinel, he’s also the coach of a Jewish high school team, David Posnack Jewish Day School. If you saw that coming, you should start a 1-800 psychic line and let me know so I can invest in your business.

When Anderson first admitted interest in the position to a father of two Posnack students, the interest was relayed to Posnack Athletic Director Mitch Evron.

“Yeah, I’ll talk to Kenny Anderson,” said Everon. “I’ll talk to Dwyane Wade, too.”

But Anderson’s interest was real. Never mind that he would make less than $2,500 in his new position. He sees coaching at Posnack a real challenge, one he can look forward to just years after filing for bankruptcy, after fathering seven children with five different women and being what the South Florida Sun Sentinel describes as a “distant” father to all of them.

“My challenge after leaving the pros was going back to school, that’s the only challenge I had. And I did that,” Anderson told the Sun Sentinel. “This is another challenge, and that’s what I feed off of.”

Some people would likely consider Anderson’s new job a letdown. Here’s a former NBA player, an All-Star, who made more than $63 million in his career, and that’s not counting endorsements, coaching a Jewish high school team for one-eighth of Anderson’s former monthly expenses.

But Anderson lived the NBA lifestyle for a long time, and it didn’t agree with him. He lost every penny. He lost two wives. He lost the ability to pay child support. He spent millions of dollars on cars (ten or eleven of them, he once said), clothes and women, and the rest of his money he spent on his growing stack of bills and, sometimes, just loaning money to friends he knew would never pay him back.

“I was generous,” he once told the Washington Post. “I didn’t say no. I used to have it bad, people calling me, crying. I used to be like, ‘Aw, damn, man.’ They were struggling. It’s hard. My accountants, they were like: ‘No!’ I’d be like, ‘But they’re getting ready to get thrown out of their house!’ So I helped.”

And then the money, and the perks that came with it, were all gone. Rock bottom. Nowhere to go but up. So Anderson changed his life. He started to take care of himself and watch his bank account. He went back to school and graduated from St. Thomas University. He married a woman, Natasha Anderson, who Anderson said in 2009 loved him unconditionally, not because of the number in his bank account — remember, by now that number was quite low — but because of who he was. He started a point guard academy and began teaching basketball to young kids.

Anderson told the Miami Herald his old lifestyle had been empty.

“I want to be a role model,” he said. “Before I’m gone, I want to help somebody like people helped me. Not a million kids. Three. Two. One. I want one kid to be able to say, ‘Kenny Anderson helped me.’ That’s the stuff that matters.”

A month before he graduated college, Anderson remembered his mother, Joan, and his mentor, Howie Lawrence, and wished they were still alive so they could see him now. All grown up, a college graduate, finally heeding the advice they preached to him for so long, mentoring children, being a good father, taking care of his own, finally piecing his life back together and understanding what was important.

“They’d be so shocked and so proud,” he told the Miami Herald in April 2010.

And now he’s coaching a small Jewish high school team, one that has never made the regional playoffs. Anderson was advised to start small, and that seems to be part of his plan, to prove his coaching acumen at Posnack before moving on to a bigger, more basketball-oriented school. But for now, he gets the chance to give back to the community, to challenge himself, to lead and mentor and teach students, and probably even to learn a lot himself.

Maybe one day, some of the Posnack players will look back at their time being coached by Kenny Anderson and say that Anderson helped them. That’s the stuff that matters.

Currently, the players are just in shock that Anderson decided to coach a Jewish high school team with no basketball pedigree.

“It’s awesome,” said Jonah Wassersterom, a 10th-grade player.

Awesome, but only if Anderson uses his opportunity the way he should, the way that his mother, Joan, and mentor, Howie Lawrence, would have wanted him to.

Ahh, remember when Kenny Anderson was the C’s point guard?   Back when the Celtics were good enough to miss out on the lottery but never good enough to contend for a championship?

Thank God those days are gone.  This post is both a bit of reminiscing and a reminder that there is a game tonight, another series to watch. And, if #13 has anything to say about it, “the other series” should be fun.

Is it just me, or did young Kenny Anderson have a whole lot in common with Brandon Jennings?

But the similarities between the two lightning-quick lefties isn’t the part of this highlight reel that interests me the most.  That honor goes to the Vinny Del Negro sighting at 2:15 in the video.  I know exactly what Del Negro was thinking while he watched the soon-to-be-graduate Anderson jet by him:

“I can’t wait to become a head coach so I can burn as many timeouts as I want. Muahaha.”

From rags to riches and all the way in between.

Educate. Cap. Gown. Hand shake. Diploma.  Cheers. Family. Friends. Pride. Throw cap in air. Celebrate. Enjoy. Improve.

*****

College graduation was never supposed to be a big day in Kenny Anderson’s life.  He had bigger, better things to do than pick up a piece of paper symbolizing years of hard work and achievement, the end of one chapter and the beginning of a next.

He left college after two years, remember?  He was the second pick in the 1991 NBA Draft.  He was an NBA All-Star.  He made more than $60 million, all to play a game.  Who the hell needs a diploma, anyway?  Anderson wasn’t on top of the world, but he was far closer than most individuals would ever come.

And then he crashed. He crashed hard, and he crashed quick, with a big thud. His mother died, of a heart attack. His mentor, Howie Lawrence, who helped pay for Anderson’s high school tuition by working three jobs, passed away too. He broke up with two wives.  Lost the ability to pay child support for his children.  The $60 million disintegrated. Anderson was forced to declare bankruptcy, blowing money partially because of what he calls ghetto loyalty.

“I didn’t listen to my advisers,” Anderson says. “I just couldn’t say no to my family and my community. They made me. They watched me and protected me, the prodigy. How could I say no when someone who helped me as a kid needed a few thousand dollars because he was going to get evicted?”

“I was generous,” he says. “I didn’t say no. I used to have it bad, people calling me, crying. I used to be like, ‘Aw, damn, man.’ They were struggling. It’s hard. My accountants, they were like: ‘No!’ I’d be like, ‘But they’re getting ready to get thrown out of their house!’ So I helped.”

But it wasn’t only helping people. Sometimes, it was spending just to spend. Just to get the shiny things in life. Like a few other athletes richer than the average 9-5′er could ever dream of, Anderson spent on everything under the sun.

“I see so many of the guys in the league chasing cheers, women, money, acceptance, the press — the shiny things, as I call them,” he says. “That was me. Traveling, playing, partying, VIP.”

Anderson lost everything he had, and it took nothing less for him to finally see the error in his ways.  “I believe he had to be at the very bottom to be able to say, ‘Wow, things are different,’ ” Kenny’s third wife, Natasha Anderson, told the Washington Post in 2009. “He had to do this.”

But he couldn’t have done it without Natasha, a clinical social worker at a Miami hospital.  “Meeting Tasha,” says Irwin Levy, a friend of Kenny’s, “was huge.”

“Me and my wife — that’s unconditional love there,” Anderson says. “My other wives: infatuation. It wasn’t love. It was just something to do.”

“She just loves Kenny,” says Dick Gilbert, another of Anderson’s friends, and also a mentor. “Some of the other ones didn’t love Kenny. They loved what Kenny could bring.”

“I loved Kenny unconditionally,” Natasha says. “The only other woman who’s ever done that was his mother. And I think he first saw that after he realized he wasn’t making millions anymore, and he didn’t have all the cars and the houses — and I didn’t turn my back on him. We were going to do it together. If you fell, I fell.

“I think that’s really what it was — having that one person who loves him just like his mother did.”

Anderson’s mother recognized it, too.  Just before her death, she told Anderson, “Keep that. That’s a good woman.”

And so Kenny and Natasha Anderson marched back from the depths of bankruptcy.  And they did it by themselves.

“As an athlete, everyone always holds your hand,” Kenny says. “Nobody has been holding my hand the last few years. I do for myself. I challenged myself. I sacrificed. I did something. I do the bills now. I wash dishes. Laundry. I’m the nanny.”

Wow, you say, he does the laundry and the dishes. Whoop-de-doo. But, for Anderson, it was a drastic change. This is a man who had everything given to him, from an early age. He was the first high school player since Lew Alcindor (later Kareem Abdul-Jabar) to be a three-time Parade All-American. He entered the NBA as its youngest player, and soon became an All-Star. He made piles of cash, and spent it on everything under the sun. He had ten or eleven cars in his garage at one point, and they weren’t Hyundais. He paid mounds of child support, loved bling and pretty women, and totaled $41,000 in expenses each month. “The thing people don’t understand is, it sounds like a lot of money — 60 million — but there’s Uncle Sam,” he told the Post. “There’s agent’s fees, financial advisers, houses, allowances for family members who don’t even work.”

His old lifestyle was fun and left Anderson famous, but it left a lot to be desired. “It’s empty,” he says. “I want to be a role model. Before I’m gone, I want to help somebody like people helped me. Not a million kids. Three. Two. One. I want one kid to be able to say, ‘Kenny Anderson helped me.’ That’s the stuff that matters.”

He runs a basketball academy now, the Kenny Anderson Point Guard Academy, and lives a comfortable life.  He no longer has a mansion, but a nice, $400,000 house.  He doesn’t have ten or eleven cars anymore, but does drive a Cadillac Escalade.  He doesn’t have a maid, but makes do by doing his own work around the house.  He’s successfully — and finally — put the NBA in his rearview mirror, adjusting to Life After Retirement.

Next month, Anderson will walk across the stage and pick up his diploma.  More than two decades after entering Georgia Tech as a spindly freshman with a reputation befitting a hoops god, he’ll graduate St. Thomas University as a humbled but happy man who finally figured life out.  The hard way.

“You know what?” Anderson says. “That day is going to be a lot better than when my name was called second in the NBA Draft and they put on my hat on stage. A lot better.”

But not perfect.

“If Mom and Howie saw me now,” Anderson says, recalling his mother and mentor. “Being a good father. Going to school. Mentoring kids. Taking care of my own. They’d be so shocked and so proud. I’m doing something I didn’t think I could do. It took me a while, but I finally learned their lessons.”

All those lessons, and the pain and heartache it took to learn them, are why throwing his cap in the air will be oh so sweet.

*****

Educate. Cap. Gown. Hand shake. Diploma.  Cheers. Family. Friends. Pride. Throw cap in air. Celebrate. Enjoy. Improve.

It took Kenny Anderson longer than it does for a lot of others, but he’s finally pointed in the right direction.

Quotes from the Miami Herald and Washington Post were used in this piece.