After navigating through another successful offseason by landing Gordon Hayward in free agency, the next major decision on the docket for Danny Ainge is determining what Isaiah Thomas will be worth in the summer of 2018.

The 5-foot-9 guard exceeded everyone’s expectations yet again during the 2016-17 season by transforming himself into a second-team All-NBA guard and one of the top scorers in the NBA. Thomas will also be one of the best bargain contracts in the league for at least one more season, as his $6.2 million salary in 2017-18 represents the final year of his deal.

Thomas has made no secret about his desire to be paid more, and he’s well within his rights on that front after playing on an under-market pact since 2014. The question the Celtics will need to ask themselves in the next year is whether they want to pay the 28-year-old the type of money ($30.4 million would be his starting max) he may command on the open market. Ainge has shown a history of moving on from valuable future free agents-to-be (see: Kendrick Perkins, Rajon Rondo, Avery Bradley) before they have a chance to walk away for nothing.

The odds of Thomas remaining in Boston long term increased considerably this offseason in my opinion, based largely on the moves the Celtics have made. A potential point guard of the future (Markelle Fultz) was passed on in favor of Jayson Tatum. Another free agent in line for a future payday next summer (Bradley) was moved preemptively for Marcus Morris. A second All-Star was added to the mix in Hayward, making Boston a team that’s built to give the Cavaliers a run for their money sooner rather than later. I doubt Hayward agrees to come to Boston if Isaiah weren’t a part of the team’s long-term plans too.

While it makes more sense than ever for Thomas to remain in green from a competitiveness standpoint, the kind of market Thomas will see in his next deal has been hotly debated. In order to effectively answer that question and get a better sense of Ainge’s long-term planning, let’s take a look at the factors that will help determine the next payday for Thomas:

1) The point guard position is incredibly deep around the league

If you take a look around the NBA playoff picture last year, you won’t find too many teams with holes at the point guard spot. Other top teams in the East are fully set at point guard (Kyle Lowry, John Wall), while many other potential playoff teams have big money or young elite talent already committed to the position (Charlotte, Detroit, Miami, Philadelphia). The same holds true in the Western Conference where you’ll only find a few playoff teams (LA Clippers, San Antonio, Utah) where you would qualify Thomas as a major upgrade at the point guard spot.

There are certainly teams around the league that need serious help at point guard (Orlando, New York), but are those the franchises that want to be investing $25-30 million per year in a 5-foot-9 guard who will be 29 when he hits the open market?

There’s also another side of this situation that favors Boston. The reduced salary cap estimate ($102 million for 2018-19) has created an environment in which it’s hard to find a team that a) needs a veteran All-Star point guard, b) wants to compete right away, and c) has enough salary cap room available to make a significant offer.

Let’s first examine point guard signings around the league this offseason to try to get a better sense where the market is.

2017 notable point guard signings

Steph Curry at age 29: 5 years, $201 million (Warriors)

Kyle Lowry at age 31: 3 years, $100 million (Raptors)

Jrue Holiday at age 26: 5 years, $125 million (Pelicans)

George Hill at age 30: 3 years, $57 million, third year unguaranteed (Kings)

Jeff Teague at age 29: 3 years, $57 million, third year player option (Wolves)

Analysis: Curry got the super max, as he should have. Lowry was eligible for a 35 percent max with 10+ years of experience, but he came up a little shy of that. Getting only three years has to be considered a surprise too. Holiday got overpaid in my opinion, but he also held plenty of leverage over a Pelicans team that had no cap room to replace him with if he walked. With DeMarcus Cousins on an expiring deal too for 2017-18, Holiday’s agent had the Pelicans over a barrel and he did well for his client. I would imagine Thomas' agent would use this Holiday deal to ask for a max contract since he can make the case Thomas has been the better player than Holiday for a couple years now.

It’s safe to bet Hill and Teague’s deals are encouraging from Boston’s perspective since they were for reasonable money and just three years in length. Hill’s contract in particular was surprising since he had to settle for a third non-guaranteed year. Fewer than four years is generally a good thing when you are signing a non-star player at 29.

2) Most teams have point guards already under contract for 2018-19

Teams "set" at point guard in 2018-19:

Charlotte (Kemba Walker), Golden State (Curry), Houston (Chris Paul), Memphis (Mike Conley), Miami (Goran Dragic), Minnesota (Jeff Teague), New Orleans (Jrue Holiday), Oklahoma City (Russell Westbrook, if he re-signs), Philadelphia (Markelle Fultz), Phoenix (Eric Bledsoe), Portland (Damian Lillard), Sacramento (George Hill/De’Aaron Fox), Toronto (Kyle Lowry), Washington (John Wall), Utah (Ricky Rubio)

Teams that could use a point guard, but are rebuilding and/or have young talent at point guard already:

Atlanta (Dennis Schroder), Brooklyn (D’Angelo Russell/Jeremy Lin), Chicago (Kris Dunn), Dallas (Dennis Smith Jr.), Denver (Jamal Murray), Indiana (Victor Oladipo), LA Lakers (Lonzo Ball), Milwaukee (Malcolm Brogdon)

Teams that could use an upgrade at point guard but probably won’t have cap room next summer:

Cleveland (????), Detroit (Reggie Jackson), LA Clippers (Milos Tedonsic)

Teams that need a point guard and could have cap room in summer of 2018:

San Antonio: The Spurs just re-signed Patty Mills to a four-year deal for $50 million, but Parker could be coming to the end of his career. If LaMarcus Aldridge and Danny Green opt out of their contracts, San Antonio could have max money to throw at a big name to pair with Kawhi Leonard.

New York: Cap space might be available if Carmelo Anthony opts out of his contract next summer (a big if, since he won’t be able to command $28 million elsewhere). The Knicks are rebuilding, but they are also the Knicks, so you can’t rule them out from throwing big money at Thomas to bring a star to the Big Apple to play alongside Kristaps Porzingis.

Orlando: The Magic desperately need an offensive sparkplug like Thomas, but they may not have the ability to offer Thomas max money or close to it without moving on from future restricted free agents Aaron Gordon and Elfrid Payton. I’m also not sure Thomas does enough on his own to improve a roster plagued with bad contracts. If Orlando simply wants a star name to sell tickets and create some buzz, Thomas would be an attractive piece. His age doesn’t really line up well with what that team is trying to do from a competitive standpoint, though.

Wildcard suitors

Brooklyn: There is money to spend here, but I don’t buy this possibility unless Russell flops next year. Investing in youth makes far more sense for Brooklyn at this point anyway.

Dallas: If Smith Jr. doesn’t pan out right away, the Mavericks will likely be looking for a big name to bridge the gap with Dirk Nowitzki fading into the sunset. Would the lure of big money on a non-contending team in Dallas appeal to Thomas? The Mavs will have plenty of money to spend next summer, so this is a team to watch.

Denver: The Nuggets made a big splash in free agency by landing Millsap and have plenty of young tradeable contracts on the roster for the 2018-19 season. Moving a few of those could open up the cap space to make a run at Thomas, if Denver doesn’t feel confident handing the keys to Jamal Murray just yet.

Oklahoma City: If Russell Westbrook and Paul George skip town in 2018, Thunder GM Sam Presti is going to easily have upwards of $30+ million in cap room next summer. Rebuilding is the logical choice for OKC, but they could also be looking for a new face of the franchise if they want to sell tickets.

The Celtics’ brass already know all of these looming factors about the 2018 free agent market. The salary cap is smoothing out. Elite free agents (Lowry, Paul Millsap) had to settle for three-year deals this summer. Lowry also had to settle for less than the 10+ year max. Few teams probably think they can make a serious run at the Warriors anytime soon. There are only a handful of teams that could be in position to offer Thomas max money next summer, and it’s unclear whether those franchises will believe he’s worth that kind of dough at age 29 without a chance of contending.

3) The free agent point guard market in 2018 is weak

While there may be limited teams with cap space in the summer 2018, the pickings will be very slim after Thomas for teams in the market at point guard. Here’s a list of the best floor generals that will be available next July:

Isaiah Thomas

Chris Paul (probably staying in Houston)

Marcus Smart (restricted)

Elfrid Payton (restricted)

Jeremy Lin (player option)

There will be a lot of other All-Stars at other positions out there exploring their options (Kevin Durant, LeBron James, Russell Westbrook, Paul George, DeMarcus Cousins) but once those names get gobbled up, Thomas should be a hot commodity.

4) Health

Thomas valiantly played through a hip injury for the end of the regular season and the first two rounds of the postseason, but the lasting damage of that decision still isn’t clear. The All-Star told reporters in May that he hoped to avoid surgery, and Brad Stevens indicated earlier this month that the team expects Thomas to do so and be ready for camp.

While Thomas played his best basketball of his career last year, it’s not clear to the Celtics or the rest of the league whether the veteran point guard will be at 100 percent at the start of next year. Shane Larkin’s reported signing also raised a few eyebrows as well. That type of uncertainty provides a daunting backdrop for the All-Star, particularly as he heads into a contract season. If Thomas stays healthy and matches his incredible production from last season, it’s safe to guess a couple teams could buy into the idea of paying Thomas max money.

Conclusion

When you assess all of these variables, it’s easy to see why the Celtics believe they will be able to sign Isaiah for less than the max next summer. Even with the weak point guard crop, it doesn’t look like there will be a lot of teams in the market that will pay an older guard max money, especially when you consider Isaiah’s limitations on the defensive end.

Thomas will likely get his money from Boston (they won’t have the salary cap room next summer to find an adequate replacement) but the Celtics will be facing significant luxury tax concerns next year as well, particularly if they want to keep Smart as well. Any dollar the Celtics pay Thomas could end up being multiplied by three for ownership when you factor in luxury penalties that will loom in 2018-19. Boston isn’t going to bid against itself.

The starting point guess here is about $25 million per year (a bit higher annually than Jrue Holiday’s deal) and that number goes up if Thomas delivers the goods again in 2017-18. Thomas will be able to back up the Brinks truck next year, but the guess here is he won’t be filling it to capacity.

All salary information via Basketball-Reference.com

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