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The Once and Future Celtics

Down 2–1 to Cleveland, is Boston one player away from competing for the title, or should it be building for a post-LeBron world? These are the questions Danny Ainge will have to answer as he considers what to do with his no. 1 pick in the draft and possible pursuit of Gordon Hayward.

(Getty Images/Ringer illustration)
(Getty Images/Ringer illustration)

While I was walking back to the media room after the Celtics’ 130–86 Game 2 loss to the Cavaliers, a fan wearing an Isaiah Thomas jersey shouted my name. "Is Markelle Fultz gonna fix this?" he asked. I smirked and said, "Nah. Neither will Gordon Hayward." There was a pause, and then we both laughed. When the Cavs and Warriors are playing like this, what else can you do?

Go to Cleveland, and win without Isaiah Thomas, apparently. Boston’s unexpected 111–108 Game 3 win, on the road, minus the Little Guy, shows why so many fans want to go all in on this group. Athletes like to use being counted out as motivation, which is usually baloney — but on Sunday, it was true. For all the gossip about how a sweep would negatively impact Boston’s free-agent hopes, the win confirmed why the Celtics are a viable destination in the first place.

Boston can essentially go in any direction. The team won 53 games this season, has one of the game’s top head coaches in Brad Stevens, went all the way to the Eastern Conference finals, has a ton of young talent, owns the no. 1 pick, and can easily create cap space to sign a max free agent this summer. President of basketball operations Danny Ainge holds an amazing hand.

Marcus Smart showed what he’s capable of during the Celtics’ Game 3 victory, draining seven triples on his way to 27 points while dishing out seven assists and playing excellent defense. I’ve long been a Smart apologist, and you can’t help but wonder if he’ll experience some late-20s offensive surge, à la Kyle Lowry. Avery Bradley hit the game winner while slithering through screens to contain Cleveland’s perimeter players.

But those who take a glass-half-empty view of the team will note that the Celtics have it all and nothing, all at once. Thomas, Bradley, and Smart are all free agents next summer, and they will all be looking to get paid. There are no guarantees the Celtics will be able to make a big signing this offseason. Ainge’s goal is to hang more championship banners, not win division titles, but how can he do that when there are two massive roadblocks in the way: LeBron James and the Warriors.

As the Celtics plays out the string in an Eastern Conference finals series in which they are down 2–1, here are the big questions as the storied franchise arrives at a crossroads.

Can Boston Build for Both 2018 and 2025?

The Celtics’ plan last summer appeared pretty straightforward: add Kevin Durant and Al Horford while retaining the 2017 and 2018 Nets picks. They’d have a title-contending roster with picks to build for sustainable playoff runs deep into the 2020s. But Durant went to Golden State, and now they’re left with … well, still a pretty damn good team. Horford plays like the irreplaceable super-glue guy of a championship starting lineup. Even without Durant, Boston can continue on the same patient-and-reactive path the team has followed for years. The team’s mixture of picks, youth, and veterans, enables them to develop and compete. "Sometimes you need to be patient," Ainge said on lottery night. "It’s hard for me to be patient. I like action, but we have a good group of guys around us. My whole staff, ownership, we sit and calmly try to figure out what the best path is to take. We don’t want to make any mistakes and so far we’ve been pretty good."

The Celtics signed Horford using cap space last summer and will try to do the same this offseason with Gordon Hayward. The Vertical’s Adrian Wojnarowski said recently the Celtics are "really focused" on preserving cap space and going "hard" after Hayward on July 1. This doesn’t exactly come as a surprise. As we covered last week, the Jazz lost their financial advantage with Hayward not being named to an All-NBA team. Boston has an easier path to the Finals than Utah, an arguably more talented roster, and way more long-term flexibility. Boston’s odds of landing Hayward are stronger than any Jazz fan should feel comfortable with.

The Celtics can create max contract space by rescinding rights to their pending free agents (Kelly Olynyk being the most notable name), and making a trade that moves a salary worth roughly $4.5 million or more (depending on what they do with 2016 draft-and-stashes Ante Zizic and Guerschon Yabusele). Jae Crowder, Avery Bradley, or Marcus Smart would likely need to be dealt to make room for the Jazz swing man. Crowder has one of the best value contracts in the league, so in theory he could bring back the largest return. It’s not that simple, though.

The addition of a player can affect others on the roster. If the Celtics draft Markelle Fultz with the no. 1 pick, Fultz will carve into the minutes of Smart and Bradley (and the rest of the guards). If they sign Hayward, Crowder will see a significant dip in responsibility — and he’s more than once voiced his displeasure about Boston fans fawning for Hayward.

No matter who gets moved, Hayward alone isn’t enough to get Boston over the LeBron hump, especially if the team is subtracting another key rotation player. The Celtics need two players to even have a chance of beating the Cavaliers or Warriors — that’s why they didn’t dump all their assets at the deadline for Paul George or Jimmy Butler. "We figure we’re probably two guys away from being a really, really good team; probably two significant guys away," said Celtics owner Wyc Grousbeck in February. "If we put all the chips in on one guy, we’re getting rid of draft picks and we’re getting rid of free agency this summer … it’s sort of like one step forward, two steps back."

The Celtics could theoretically sign Hayward and then make a push for George or Butler. The math to make it work is complex, but it’s doable. Is it worth it, even if it means giving up Fultz? Maybe. Once it came time to re-sign everyone in 2018, Boston’s payroll would soar deep into the luxury tax — ownership would be paying for the NBA’s most expensive collection of players, and the team still might not be the favorite.

The question is, are they building for 2018 or 2025 — or both? There are no guarantees a deal would require sending Fultz or even Jaylen Brown, but keeping them would assure the ability to build for the present and future. The Celtics will have the rights to Fultz for at least eight years until he’s an unrestricted free agent in 2025. Fultz will be 27 that year. Brown will be 29. George would be 35, and Butler would be 36. "In this day’s NBA, picks are very, very valuable. You have a young person that you can help mold and grow with," Grousbeck said the morning after the draft lottery. "Bring him in before the max salaries kick in. [It] makes a lot of sense to keep these picks."

Keeping the 2017 and 2018 picks would enable Boston to keep competing now while also having a young roster built for sustainable success into the next decade. The Celtics would also retain those assets for a bigger fish from the next wave of trade targets, rather than dumping them now for a short-term gain that still might not be enough to beat Cleveland.

If the Celtics, of all teams, end up running into the LeBron brick wall every postseason no matter which path they choose, what does that say for the rest of the East? It’s not like every team can punt the next three or four years away and hope LeBron gets old. The King is better now than ever. The Eastern Conference can’t wait out LeBron. He may not regress until the next decade.

Which Guards Get Paid?

So many offseason discussions — including this one — seem to assume that Hayward will be suiting up for Boston next season. But nothing is certain. Hayward could decide to re-up with the Jazz, leaving the Celtics with a boatload of cap space. The Celtics have two starters in Thomas and Bradley with only one year left on their contract, and Smart, who will be a restricted free agent in 2018. Thomas wants the Celtics to bring out the Brink’s truck. Bradley may receive offers of over $20 million per year. Smart will see money bags with more nights like Game 3. They also have the productive Terry Rozier, and possibly an incoming Fultz. Don’t get too attached to this Boston backcourt, because realistically, Ainge can’t bring everyone back.

Conventional wisdom would suggest Thomas is absolutely going to stay. The Little Guy is a magic factory on the basketball court — his season has been, by far, one of the most inspiring and exciting I’ve ever watched.

The 53-point performance against Washington was truly magical, but just from a pure aesthetics standpoint, he’s a 5-foot-9 guy who plays with so much love and energy. Despite the death of his sister, getting a tooth knocked out, going through oral surgery, and ultimately suffering a major hip injury, Thomas still led his team to the Eastern Conference finals, and was rewarded with an All-NBA second-team slot. He was Allen Iverson 2.0, posting one of the most efficient high-scoring seasons ever. Iverson took at least 24 shots per game in all of his five seasons in which he averaged over 28 points. It took Thomas only 19.4 shots to average 28.9. Thomas deserves to be rewarded with a max contract, but there are no guarantees Ainge gives it to him.

You can bet Thomas, who will earn a measly $6.3 million in 2017–18, would be open to renegotiating his contract like Russell Westbrook did this past summer. Thomas would be eligible to renegotiate-and-extend on July 12, three years after signing his deal with Phoenix.

If the Celtics had cap space, they’d be able to do it. But it seems unlikely they’d be willing to do so considering their ambitions of making a splash. Even if Hayward is off the table, re-signing Thomas now would make it harder to do big things during the season or next summer. They’d be locked into a roster that’s good-not-great, similar to the dilemma facing the Raptors. There’s also the fact that Thomas will be 29 next year, he’s a 5-foot-9 point guard one year removed from a labral tear that ended his 2017 season and could require surgery this offseason. In 2018, he’ll be a free agent eligible to sign a five-year max contract worth roughly $180 million. The Celtics’ offense struggles when Thomas is off the floor, but add Hayward and Fultz, among others, and they’d have more options.

No matter how great Thomas is offensively, he’ll always be a target on the other end of the floor. "Isaiah’s a big loss for them offensively but I think they get better defensively," Cavs head coach Tyronn Lue said before Game 3. He was right: Boston’s defense was crisper. Isaiah isn’t the revolving door he’s made out to be, but he is a minus. Playoff teams played seek-and-destroy with Thomas, and that’ll never change no matter how the roster looks.

In Boston’s Game 7 win last round, the Wizards attacked Thomas at will until he was pulled midway through the third quarter for Smart. Stevens’s substitution changed the game. We know now that Thomas was hurt at the time, but this was a common occurrence during the regular season. Isaiah’s stunning scoring makes his dismal defense worth it. But if the Celtics start adding offensive pieces like Hayward and Fultz that limit Thomas’s offensive role, his usage, and his scoring opportunities, then it’s hard not to wonder if a max contract is an overpay because of his role responsibility, and not just his defense.

Meanwhile, Fultz will cost an average of only $7.9 million annually over his rookie deal. The cost of championship point guards over the past 25 seasons is insignificant. Starting point guards on title teams since 1992 account on average for only 11.3 percent of the cap, about the equivalent of Austin Rivers this season. Title teams generally rely on veterans (like Derek Fisher) or younger guards (Rajon Rondo, at the time). Or, maybe Fultz.

Without re-upping Thomas or making other cap-filling acquisitions, the Celtics would need to reach the minimum salary threshold, which they could do by retaining Olynyk or Tyler Zeller, or journeymen like Amir Johnson or Jonas Jerebko. They could look at second-tier free agents like JaMychal Green, too.

Or, they could look to trade for Carmelo Anthony, who would cost significantly less than what it’d take to acquire Butler or George. I made the case in January that Melo would provide Boston a best of both worlds approach. The New York Post’s Marc Berman speculates the Knicks would target Crowder in return, which seems unlikely considering Crowder’s contract value and the fact the Celtics would need to give up an additional piece to make it work financially. Melo has a no-trade clause and he might prefer to stay in New York.

The question of who stays and who goes could simply answer itself this summer whether or not a trade is made to move salary for Hayward. The Celtics will have options, and they won’t be rash. They’re sitting on a goldmine of assets and they won’t give it up unless it puts them in a real position to compete for titles — not an enhanced version of this mirage we witnessed in this year’s playoffs. Boston could always reboot by cashing out on their stars of today. Ainge has made it clear in the past that "nobody is ever untouchable." The 2017 and 2018 drafts are loaded with potential cornerstone players. From Fultz in 2017 to Michael Porter Jr. and Luka Doncic in 2018, the next two drafts include prospects that will define contenders in the 2020s. If the Celtics are able to push all their chips onto the draft picks table, it’s something they should at least think about.

Do Thomas and Fultz Fit Together?

If Thomas can produce in three-guard lineups with Smart and Rozier, as he did the past two years with Smart and Evan Turner, there’s no doubt he’d be able to move forward with Fultz. "Isaiah can play with anybody. He can play 2-guard. He can play whatever," Ainge said after the lottery. "He’s just a basketball player. He’s a scorer, and he’s a great off-the-ball player as well."

The ball being taken out of Isaiah’s hands is nothing new. One of the primary reasons Thomas has scored so effectively is how Brad Stevens uses him off the ball.

Thomas knocked down 39.9 percent of his catch-and-shoot 3s, per SportVU, while running through a heavy dose of off-ball screens like the one above. In spot-up situations, Thomas could unload 3s, or attack a rotating defense. Stevens put Thomas in similar live-dribble situations by running him through dribble-handoffs. Thomas finished possessions using dribble-handoffs more than any other player in the NBA with 216 total, 13 more than the next closest (J.J. Redick), while no one else cracked 200, per Synergy Sports.

Thomas could drive, jack up a 3, or draw a foul out of this play type, and it has worked to great effect all season. No matter what other personnel is on the floor, it’s something they can lean on.

Guard is already the team’s strongest and deepest position, and Fultz wouldn’t suddenly cause Boston to make the leap. However, he would provide significantly higher long-term upside and stability at the position. "We certainly don’t have expectations for a no. 1 pick to come in and turn our franchise around and make us a better team than where we are right now in the final four," Ainge said after the lottery. "I think that they can add to our team and help us in some capacity, but I think it’s dangerous to think that a 19-year-old’s going to come in and transform our franchise."

Even with a trade for a superstar, the Celtics will need to reshuffle the middle and back of their roster. Gerald Green, Jerebko, and Johnson, who wears cinderblocks for shoes, will all be unrestricted free agents. Tyler Zeller has a nonguaranteed deal. Kelly Olynyk is restricted, and it wouldn’t be stunning if a team overpays for his services. James Young needs to get his passport ready for a business trip to China.

Boston has holes to fill with reinforcements on the way: 2016 first-round picks center Zizic and forward Yabusele are more than likely to make their way to the NBA for the 2017–18 season. D-League stash Abdel Nader could come, too.

Zizic would bring energy, patrol the paint, and help the team’s rebounding woes. The 20-year-old Croatian rebounds basketballs like he’s Super Mario collecting coins. If Stevens chooses to start a two-big lineup, Zizic is a strong candidate to begin games alongside Horford.

At 6-foot-8 and 270 pounds, Yabusele is built like a bulldozer. He’s nimble, though — a perimeter player who can shoot 3s and rumble down the lane. "I’m not saying he’s Draymond Green. It’s sort of sacrilegious to tell a rookie they’re going to be a great player. But he does have good feet, and he has good length, and he has good strength," Ainge told CSNNE after the 2016 draft. "He’s got good touch around the rim. He can actually stretch the floor. At 270 pounds, he’s a pretty good basketball player who can pass, handle, shoot a little, post up a little. He’s pretty complete."

Nader was a 3-and-D wing/forward hiding in plain sight in last year’s draft. At 6-foot-6 with a 7-foot-1 wingspan and athleticism, it’s hard to understand why he fell to 58th. Nader needs to get better at draining 3s — he hit only 33.3 percent of his 318 attempts in the D-League last year — but he certainly has the tools and the bounce to compete defensively as long as he’s hitting shots on offense.

Never mind the addition of a no. 1 pick like Fultz or a free-agent signing like Hayward, the Celtics have upgrades coming internally with Zizic supplanting Johnson, Yabusele taking Olynyk’s spot, and Nader in place of Jerebko. The Celtics also have the 37th, 53rd, and 56th picks in the draft to round off the back of their roster and the new two-way contract roster spots.

The Celtics will be better and deeper next season. The heights they reach, however, isn’t totally in their hands. "We are engaged and intense on a daily basis talking deals and finding ways to get us to the top," Ainge said. "There’s just a lot of good fortune. There’s a lot of luck involved."

An earlier version of this piece omitted Jaylen Brown.