It didn’t look like it was going to happen, but the Boston Celtics have struck a deal to keep their talented point guard in the green and white for another five years.

Facing a Monday deadline, the Boston Celtics and Rajon Rondo have reached an agreement in principle on a contract extension, his agent confirmed to ESPN The Magazine’s Ric Bucher.

The deal is for five years and will be worth at least $55 million, a source confirmed to Bucher.

Rondo and the team agreed to the deal late Sunday night, thanks in large part to what the 23-year-old point guard has demonstrated since training camp began.

General manager Danny Ainge and owner Wyc Grousbeck balked at giving Rondo the kind of deal he wanted because of concern about his leadership skills and integration in the team fabric when negotiations began.

“They were candid and we understood,” said Rondo’s agent, Bill Duffy. “It was never about on the court. They wanted him to demonstrate being more of a leader, meshing with the team, being engaged in the locker room. Those issues have been squelched. I have to give a lot of credit to Ainge and Wyc. When there is an issue and you get it resolved, it’s like a cleansing.”

Give credit to both sides for avoiding the intractability that so often prevails when a pending restricted free agent isn’t being offered what he (or his camp) believes that he’s worth. Back in June, I pegged Rondo’s value at $9.0-$10.0 million per season, and it looks like he was able to get a contract worth $11 million per year. I devalued Rondo somewhat due to his reputation, but now that the Celtics believe that it’s a non-issue, it makes sense that they’d feel he’s worth a bit more.

He still struggles with his shot, but he’s savvy around the rim, and is a great defender, rebounder and playmaker. He nearly averaged a triple-double in the playoffs when the Celtics were without Kevin Garnett.

I wouldn’t call this a great signing by the franchise as I think Rondo’s inability to shoot limits his upside somewhat, but it looks like the two sides struck a pretty fair deal given everything else that he brings to the table.

Around this time last year, I tried to estimate the kind of contracts the big name players from the class of 2004 and 2005 would sign, and here’s how I fared:

All in all, I think I did a pretty good job. Of the 12 players that signed a contract last summer, I correctly predicted the range for seven and was within $1.5 million for the other five. Granted, I underestimated what the Lakers would give Vujacic, but I find him so annoying that I have a tough time objectively determining his worth. (Though it should be noted that he didn’t do anything this season to justify $5.0 million per season.)

This year, I’m going to list the top names from the class of ’06 to try to determine what kind of extension they’ll get if their current teams choose to lock them up this summer instead of letting them hit restricted free agency in 2010. (I’ll tackle the restricted free agents of the class of ’05 in my free agency preview, which will run on 6/29.)

Due to the economy and the unwillingness of most owners to spend, the summer of 2009 promises to be tougher for free agents than years past, so we may see a few players stubbornness get the best of them. One executive predicted a “nuclear winter” of sorts, so at the very least, it will be interesting.

So here are the top players from the class of ’06 and my best estimate of the kind of money they’ll command. I’ll list their age, Player Efficiency Rating (PER), along with a few comparables.

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