What to do about the Isaiah Thomas and Marcus Smart contracts?

With the Celtics’ summer moves complete or on the way, it is natural to look towards what is next. Well…after you finish dreaming up lineup combinations for days, watching Jayson Tatum highlights, and thinking of how the Celtics can take down the Cavaliers and ultimately the Warriors to bring home banner 18. But when you have to have a short- and long-term view, as Danny Ainge does, what is next on the roster-building path is never far from your mind. And Boston has two big items looming: new deals for Marcus Smart and Isaiah Thomas.

NBA teams have until October 31^st each year to sign players who are heading into the fourth year of their Rookie Scale contract to extensions. This year, this deadline applies to players who were drafted in the first round and signed in 2014. That class includes players like Andrew Wiggins, Jabari Parker, Joel Embiid, Aaron Gordon, Dante Exum and the Celtics’ own Marcus Smart. Players entering their fourth year can sign an extension that kicks in the following year. For recent examples, think of Giannis Antetokounmpo or Rudy Gobert last summer. They both signed extensions in 2016 that start in 2017-18. Should Boston and Smart reach an agreement on an extension, it would begin with the 2018-19 season. Smart will play out 2017-18 on the fourth year of his Rookie Scale deal at $4,538,020.00.

If the Celtics and Smart can’t reach an agreement, he’ll be a restricted free agent in the summer of 2018. Boston will assuredly tender him a qualifying offer. That means the Celtics will have the opportunity to match any offer Smart may get as a restricted free agent.

Sometimes it is hard to believe Smart is already starting his fourth year. In many ways, he still seems like the hard-nosed rookie who came in with NBA-ready defense and a questionable offensive game. While the defense is still there, as Smart can capably guard 1-4 for portions of games, the offense remains a question mark. But that is an oversimplification and ignores some quality improvement he has made.

In his third year, Smart played in a career-high 79 games, starting 24, and he scored a career-best 10.6 points per game to go along with 4.6 assists per game. He became a far better playmaker, especially in pick-and-roll actions. He’s more decisive now and confident in his decision making. He understand the importance of delivering the ball on time and in the right spots to his teammates. He’s also tightened up his handle and doesn’t commit nearly as many careless turnovers as he used to. Now his turnovers are more an act of trying to make a play, as opposed to just losing the ball. These are all key markers of growth for a young player, especially one who plays the point guard position a lot.

But the old bugaboo of shooting the basketball remains. Smart shot 35.9 percent overall and just 28.3 percent from behind the arc, despite getting up 332 three-point attempts. He does confidently shoot the ball without hesitation, but his shot all too often remains flat. He also shoots what scouts call a heavy ball. This means that the shot comes off his hands with great velocity and with little arc. It either goes straight through, or it caroms off hard. For those of you who are football fans, think of a touch passer floating one in versus a quarterback firing laser beams. The best can do both. Smart, to this point, launches rockets only. Sometimes it works, but, all too often, it doesn’t.

All that said, there are some signs of shooting improvement if you squint hard enough. He took nine heaves, as he’s one of the few NBA players who disregards his shooting percentage and launches end-of-quarter shots from anywhere. While not enough to swing it big time, it did cost him one percentage point on his average. More importantly, he realized the value of the corner three. He took 22.3 percent of his triples from the corner, where he hit a career-high 41.9 percent. Almost every NBA shooter hits for a higher percentage on the shorter corner three than elsewhere around the arc, but getting those shots is important. Whether it was Smart realizing it or a function of the offense, look for him to get more shots from there going forward.

Most important of all, he raised his free throw shooting percentage up to 81.2 percent. He has gone from 64.6 to 77.7 to 81.2 percent over the last three years. For a guy who Boston wants on the court at the end of close games because of his defense, he needs to knock them down at the charity stripe. And this wasn’t a function of less attempts either, as he attempted a career-high 250 free throws.

Smart isn’t likely to ever be a knockdown shooter. It is rare to see players make that big of a swing multiple years into their careers. It rarely happens. For every Jason Kidd, there are 100 players who never get there. But if he can focus on what he does well offensively, Smart should be just fine.

Which begs the question: how much do you pay an elite-level defender with a limited offensive game who plays the guard position? Big men who are elite defenders get paid because they generally provide rim protection and rebounding. Wings are next, because every team has elite scoring wings that need to be shut down. Guards have had a different sort of go of it. Tony Allen, who is regarded as the benchmark for defensive guards, has never made more than $5.5 million in a season.

For Smart, the issue with extending him isn’t about cap space or matching an offer as a restricted free agent. The cap space ship sailed when Boston added Gordon Hayward at the max and several pricey rookies over the last two years and, presumably, this coming year. At issue with a new deal for Smart is how much the Celtics ownership is willing to spend in luxury tax payments and making sure they don’t create an untradeable player with a bad deal.

It is fair to expect the Celtics to lowball Smart in discussions that take place prior to the October 31^st deadline. If he is willing to take a team-friendly deal, Boston will gladly sign him to it. If not, they’ll let him reach the market in 2018. As he’ll be a restricted free agent, this isn’t without risk. The Washington Wizards were forced to pay more for Otto Porter than they wanted, but with no viable way of replacing him, they had to retain him. But circumstances can and do change. For one, there doesn’t project to be nearly the amount of cap space available next summer as there was in 2016 and 2017. Second, while the Celtics would lose a valuable player in Smart, they still have Terry Rozier around, and they have draft picks coming that could conceivably replace Smart in the rotation. This gives Boston a bit of leverage others in their situation haven’t had.

For those reasons, and Boston not worrying about Smart’s cap hold due to not having cap space anyway, expect Smart and the Celtics to bypass an extension at this point. They’ll certainly talk, but barring Smart taking less than he may be able to get next summer, talks will be tabled until that point. They’ll re-engage in 2018 and see where things go from there.

Isaiah Thomas is in an entirely different situation. Because Boston used all their cap space this summer, they can’t sign Thomas to an extension at this point. A new deal for Thomas will have to wait until next July. But the bigger point is: how far should the Celtics go to keep him in green?

A million words have been written about Thomas and his offensive gifts and lack of defensive ability. Only slightly fewer words have been written on how much he’s meant to the Celtics and the city of Boston. Some have now taken to calling Thomas “The Reason” because he was the reason the Celtics landed Al Horford and Gordon Hayward in free agency the last two years.

Coming off an All-NBA 2^nd team appearance, Thomas is in prime position to get paid. He signed a sweetheart deal that has actually declined in annual value over the life of the contract. For 2017-18, Thomas will make just over $6 million. No matter how bad his defense may be, if he delivers on offense, that is a bargain. Thomas is one of the NBA’s best offensive weapons, able to take over games at will, and the Celtics have figured out how to get the maximum from him. His bargain contract, as much as his play on the floor, helped Boston land both Horford and Hayward in back-to-back summers.

Now he’s up for the first big payday of his NBA career. Thomas has said in the past that for his new contract: “They’ll have to back up the Brinks truck”. But does that mean a max deal as many are assuming? For a guy who will have made less than $30 million total in his career, is he looking for a huge contract? Or is Thomas content to take a bit less if that is for the good of the team?

If the cap settles at $102 million, as last estimated by the NBA, Thomas’s max in his first year will be $30,900,000.00—more than he’s made in his entire seven-year career to that point. Thomas is not eligible for the Designated Veteran Player or so-called “Super Max”, because you have to be given that by the team that drafted you or by a team that trades for you while on your rookie contract. Even if Thomas repeats his All-NBA performance, he’s locked in to the 7-9 years of service tier for a max contract.

But back to the question: will Boston have to pay that much? Re-upping with both Thomas and Smart would launch the Celtics deep into luxury-tax territory for the first time since the Paul Pierce/Kevin Garnett era. Ownership has indicated they are happy to pay the tax for a contender, and keeping both players is key towards being a contender.

The guess here is that Thomas won’t insist on a max. He’s going to get paid a ton of money either way, and he doesn’t seem like the type who has to extract every dime he can get. By taking even slightly less, it could free up Ainge to make some other moves. The overall payroll might be the same, but the roster would be more balanced and flush with talent. Just as important for Thomas, as he approaches the age 30 barrier, are years. For a player his size and age, getting a five-year deal would be a major accomplishment and mean long-term security. That could be part of the give and take in the negotiations. Boston gives him an extra year or two, while Thomas agrees to take less than his max to give the team some tax relief and flexibility.

No matter what, the Celtics’ roster-building work isn’t done. While many have made Anthony Davis the object of desire for the next big move, the more immediate concerns revolve around Thomas and Smart. Both may be a year away from that next contract, but a year goes by very quickly. And for fans who were settling in for a long rebuild after the trade with Brooklyn, we all know how quickly things can change. Thomas and Smart were both big parts of that shift, and they’ll get taken care of accordingly sooner rather than later.