Robb: Why the odds of a Celtics trade deadline deal are higher than usual this year

Over the past four NBA regular seasons, there may not be a team across the league that has been less active than the Boston Celtics when it comes to in-season transactions. Danny Ainge earned the nickname of "Trader Danny" at some point early in his tenure in Boston but he’s worked hard to shed that label since 2015. Over that timespan, the Celtics have made just one in-season trade (a salary dump of Jabari Bird to Atlanta at the trade deadline in February 2019). Other than the signing of Greg Monroe with the team’s disabled player exception in 2018, there have been no notable in-season additions over the past three seasons. In fact, you could barely fill a paragraph of a story with all of the team’s moves in that span:

Celtics in-season transactions

2018-19

—Signed RJ Hunter to two-way contract
—Traded Jabari Bird for a protected second-round pick (salary dump)
—Signed Greg Monroe to 10-day contract
—Signed Jonathan Gibson at end of regular season

2017-18

—Signed Jarrell Eddie, Xavier Silas to a 10-day contract
—Signed Greg Monroe to 1 year, $5-million contract with disabled player exception
—Signed Jonathan Gibson at end of regular season

2016-17

No in-season moves

2015-16

—David Lee waived
—Coty Clarke signed to two 10-day deals
—John Holland signed at end of regular season

That type of track record should temper expectations leading into the trade deadline for the Celtics since recent history clearly shows the odds are against the Celtics making a deal.

However, there is a different element at play in February 2020 now that should shift the front office mindset to a degree and push the Celtics towards making their first notable in-season trade since February 2015 (Isaiah Thomas). Beyond a glaring need for depth on the bench, what could compel the Celtics to make a move now?

Roster management and diminishing returns

Heading into next season, the Celtics roster is already very crowded. Currently, 10 players on the roster are under guaranteed contracts for next season and four others have player option or non-guaranteed deals

Gordon Hayward: $34.1 million (player)
Enes Kanter: $5.0 million (player)
Semi Ojeleye: $1.75 million (non-guaranteed)
Javonte Green: $1.5 million (non-guaranteed)
Brad Wanamaker: Unrestricted free agent

Daniel Theis has a team option for $5 million that is a lock to be picked up as well due to his strong play this season.

Kanter seems the most likely piece to be out the door since he has posted strong enough numbers to try to get a long-term deal on the open market. The Celtics could still elect to bring him back with the mid-level exception but may just opt to hand the center position to Theis and Robert Williams (if he can stay healthy) and use that money elsewhere. Ojeleye and Green are both cheap useful players who know the C's system so there could be a spot on the roster for both since they each provide unique skillsets for their salaries.

Hayward’s future is the obvious wildcard here (we will have more on that at BSJ later this week) but the odds point towards a reunion in some form after the season, whether it’s Hayward just picking up the player option or signing a long-term deal at a reduced price with Boston. There will be limited suitors on the open market that can win and pay top dollar for him.

The bottom line here is the odds right now favor 12-13 players being under contract heading into free agency for Boston and that’s a very crowded roster before you even consider the C’s other assets.

—Tremont Waters will be gunning for a roster spot along with Tacko Fall. Waters will have a legitimate case to make the team after a strong campaign in Maine this year.
—The Celtics will likely have three first-round picks in 2020 and one second-round pick in the 40s.

The math here is pretty simple. Let’s be conservative and say the Celtics enter the offseason with 12 under contract (Kanter opts out, Green cut). Here’s a look at the C’s roster in that scenario when you factor in draft picks.

Under contract for 2020-21 (conservative estimate: 12 players)
Kemba Walker ($34.3 million)
Gordon Hayward ($34.1 million - player option)
Jaylen Brown ($22.9 million)
Marcus Smart ($13.4 million)
Jayson Tatum ($9.8 million)
Daniel Theis ($5 million)
Romeo Langford ($3.6 million)
Vincent Poirier ($2.6 million)
Grant Williams ($2.5 million)
Robert Williams ($2.0 million)
Semi Ojeleye ($1.8 million)
Carsen Edwards ($1.5 million)

Future assets that will require roster spot (4)
Tremont Waters (min deal)
Tacko Fall (two-way deal?)
Grizzlies pick (No. 14)
Celtics own pick (No. 23)
Bucks pick (No. 30)
Nets second-round pick (No. 45) — Two-way deal?

That leaves the Celtics with 16 players under contract potentially before the free-agent market even opens up in July (the Celtics would have the full mid-level exception to use on a player or players). Needless to say, after adding six rookies to the roster this past season, the last thing Brad Stevens would need on his way to building a contending group is adding three more inexperienced players to the mix that probably aren't ready to help right away.

The Celtics obviously would have ways of addressing this logjam after the season ends without a move now. They could consolidate draft picks, trade current selections for a future first-round pick or go with the draft-and-stash option. Dumping a player or two into an open roster spot as part of a draft deal is an option as well (similar to what happened with Baynes last June).

Still, Ainge runs the risk of being held up for leverage in some of these scenarios though. Other teams will be aware of the C’s potential roster logjam and could lowball the team with offers knowing that Ainge will have to move on from a couple of these players or picks eventually if they want to add a veteran free agent or two in July.

The Celtics have responded to this type of situation in the past by holding firm and using picks on guys that were willing to be stashed overseas to solve the issue. As we witnessed with Guerschon Yabusele (No. 16) and Ante Zizic (No. 23) in 2016, that’s a very risky route unless its a strong draft class on the international front. It also does not help a team that could be in a position to contend now.

So how does all of this relate back to the present and the possibility of a trade at the deadline? The Celtics essentially are going to have to make a trade at some point soon with all their assets, especially with the Grizzlies pick looking more likely than ever to arrive this season. Instead of kicking the can on a scenario (and potentially being squeezed for leverage by prospective trade partners), the Celtics’ brass could be better off getting aggressive and using at least one of these picks now in order to help upgrade the present roster and clear things out a bit for the future.

We have documented just how much the Celtics could use a boost in the shooting department and it’s evident right now as well that there are several pieces of the roster that Stevens just doesn’t trust. Boston’s brass still likes Carsen Edwards and Vincent Poirier over the long-term but it’s hard to imagine either guy helping this team in a significant manner this year especially in the postseason. If one is going to be the victim of an eventual roster crunch anyway in the offseason, there is little harm in using them in a trade with a draft pick to open up a roster spot at the trade deadline for a more helpful addition to the second unit.

There is no guarantee that an acceptable deal bubbles to the surface in the next two weeks for Boston but Ainge should be aggressive in finding one. A lack of depth on the bench left the Celtics exposed in the Eastern Conference Finals two years ago once injuries hit and a key injury or two would similarly sink Boston’s chances of getting out of the East this year.

A splashy addition still seems unlikely at this point due to the salary limitations but there are still a number of useful bench pieces that the C’s have the resources to acquire without risking much about their future. After years of standing pat, it’s obvious this group could use some help to have a chance against the Bucks and Sixers this Spring. With diminishing returns coming into play for future assets, the odds should turn in favor of striking now if the front office can both maximize the team's present and help plan for the future.