Did J.R. Smith make a mistake opting out of his contract?

J.R. Smith is one of the most fascinating players still on the free agent market. He is unrestricted, and can sign with any team he chooses. He turned down his player option which would have paid him in excess of $6 million. Smith will turn 30 years old in September. He's had what could charitably be described as a bumpy career. There have been real highs; Smith is a uniquely talented player who can really get it going shooting the ball. There have been serious lows; from suspensions to bad shot selection to a propensity for the nightlife.

So the question for Smith this summer would be: should he take the guaranteed money? Or try and capitalize on his strong play for the Cavaliers and get a bigger deal. And make no mistake, J.R. Smith was really good for the Cavaliers. In the 46 regular season games he played for Cleveland, Smith's true shooting rate was nearly eight points better than what he had done this year for the New York Knicks. He brought his usage rate down from 23.3% to a much more manageable 17.6%. Sure, the Cavs were asking him to do less than the Knicks were. But Smith showed he could be a team player and fulfill a role. He bought in and even defended.

The playoffs were a bit more of a mixed bag. He was suspended for two games of the second round matchup with the Chicago Bulls. He struggled in the Finals with Kevin Love and Kyrie Irving out due to injury, with his poor offense clearly leading to even worse defense. But he mixed in timely shooting before the Finals, and for the most part was dialed in. He continued to work hard and had a clear rapport with LeBron James.

The JR Smith situation is a case study for all future players with options. Never opt out of a contract without a deal in your back pocket.

— Bobby Marks (@BobbyMarks42) July 19, 2015

As we get further into free agency, Smith's deal is not done. Most guys who opt out have quasi-legal agreements largely agreed to. You very, very rarely see someone opt out and not get a bigger deal. The Cavs are in a similar position with Smith that they are with Tristan Thompson: they don't have cap space to sign a replacement for him. They can go over the cap to keep J.R., and they may yet do that. Otherwise, it's whatever or whoever they can get for the veteran's minimum.

On the other hand, the Cavs do have a bit of leverage. They know that Smith wants to be in Cleveland. They know that his checkered past means that most teams aren't all that interested in the guy. They know every dollar they give J.R. means a larger tax bill at the end of the year. Until Smith gets a big offer from someone else, the Cavs can wait for Smith's price to drop. I thought going into free agency that maybe Smith would end up missing out on the dollars bonanza. I'm feeling pretty good about that prediction now. I thought a three year, $15 million deal with a team option for the third year was a strong possibility. I'm starting to wonder if that was too much.

One of the problems with Smith is that at this point, if you give him multiple guaranteed years it might end up being impossible to move. If he can't even make it work next to LeBron James, well, it's hard to see it happening. Even with Smith on his best behavior he found himself suspended for multiple playoff games. The Cavs might need his shooting. It's likely he'll be back. They might get him at a better deal than people once thought.