The Five Worst Moments in the Celtics' NBA Draft History

Ah, what could've been. Just imagine one of the greatest, if not the greatest, power forward of all time in stunning Celtic green.

The unfortunate circumstances of the 1997 NBA Draft Lottery are just one of the few instances in Celtic history where fate has not smiled upon the franchise.

Obviously there are more good moments, than bad, but there are certainly enough poor moments for the true Boston fan to wallow in.

Aside from what I've put on the list you could also throw in the 2001 draft. The Celtics picked up a premier scorer in Joe Johnson, but soon traded him away to the Phoenix Suns. After that they picked up a pair of nobodies in Kendrick Brown and Joe Forte.

As you'll see from this list, however, it's not always about who the Celtics did or didn't draft, but about the potential that Boston missed out on.

No. Five: Chuck Share

OK, I know most of you are going, "Who the hell is this?" Believe it or not, Mr. Share was the first ever NBA Draft Pick, way way back in 1950.

The Celtics picked him first overall in hopes of making their franchise one of the best right out of the gate. Unfortunately, Share never set foot on an NBA court in a Celtics jersey.

Granted, he never turned out to be worthy of a number one overall pick, only averaging less than 10 points a game over the course of his career, but when you misfire on the first pick in NBA history, that's a big misfire.

No. Four: The Lottery

Twice in Celtics history has the franchise gone into the lottery with high expectations, with hopes of getting the pick that would enable them to find that player to bring the franchise back to glory. Yet both times they've come up with nothing.

The first instance of heartbreak occurred way back in 1997. The man on the first page of this slide show was the obvious prize to whomever secured the first pick in the draft.

Having finished with the worst record the year before, the Celtics had a 36 percent chance of coming away with the first pick, and with Tim Duncan.

Instead, fate chose to smile upon the San Antonio Spurs who have since used Duncan as the cornerstone to four titles in the past decade.

The story repeated itself a decade later, prior to the 2007 Draft where there was not just one, but two great prizes to be had in Greg Oden and Kevin Durant.

This time, based on the odds, Boston was supposed to end up with the second overall pick, which would've been the outstanding swing man above. Instead, the C's were relegated to the fifth pick.

At this point no Celtics fan is complaining, because that circumstance forced GM Danny Ainge to make the trades that led to a 17th NBA Championship, but as Durant continues to make strides towards being one of the best players in the league, this fan can only wonder what could've been.

No. Three: Reggie Lewis

Reggie Lewis already had the heartbeat of the Celtic Dynasty in him before he set foot on the storied parquet in the Boston Garden.

He played his college ball at nearby Northeastern University and Matthews Arena, the first home to the Celtics.

He was selected 22nd overall in the 1987 Draft with the Celtics hoping to erase the sad memories of Len Bias the year before.

Lewis had developed into an All-Star by his fifth season. Sadly, Lewis was torn away from the franchise by a heart condition after collapsing during an offseason practice in 1993.

His retired No. 35 remains one of only two numbers that hang in the rafters without a championship attached to it.

No. Two: The 1997 Draft

This was supposed to be the year that everything turned around. The Celtic franchise had been stuck in mediocrity or worse since the retirements of Larry Bird and Kevin McHale and the death of Reggie Lewis.

1997 was supposed to make everything better. Slick Rick Pitino was in charge and there was no way the Celtics would miss out on the top pick and Tim Duncan....until they did.

Even with two of the top six picks, things were supposed to get better, right? Wrong. Pitino selected Chauncey Billups and then tortured his poor point guard, failing to see the potential greatness that eventually showed itself in Detroit.

What was worse was Pitino trying to rebuild his Kentucky team in Boston with the selection of Ron Mercer sixth overall. If you look back at the 1997 Draft, there weren't exactly many better options. However, even among the many role players that came out in '97, several were better than Ron Mercer.

Pitino's ego quickly wore out in Boston as it was clear he was unfit to run a basketball organization with as much history as the Celtics. He couldn't handle the criticism or the pressure and was thankfully bounced out of town.

No. One: Len Bias

Perhaps the saddest story in all of basketball is the one of the great Len Bias. One of the best college basketball players ever, Bias was picked by the Celtics as the second overall pick in the 1986 draft.

The mighty were only getting mightier as Boston was coming off its 16th Championship led by Larry Bird, Kevin McHale and Robert Parish. The team was clearly getting old, however, and Bias was expected to inject new life into the team.

Instead, he got carried away at a party the night after the draft and died due to a cocaine-induced heart attack. He forever remains the ultimate "what if?" in Celtic lore.

Had he lived, he clearly would've been transitioned in as the next great Celtic leader. Boston fans would bid good-bye to the Bird era and would welcome the Bias era, which likely would've carried them up until the Paul Pierce era.

Unfortunately for Boston fans, and basketball fans everywhere, Bias remains just that, a "what if?", and a lesson for all young, superstar athletes everywhere to be careful about what goes into your body.

For a taste of how great Bias was, check out this clip on Youtube. http://www.youtube.com/watch?v=4qHB7TAoUUc