Potential Free Agent Guard Targets

It’s going to be a busy offseason in Boston. The Celtics have some room to make moves, as they have the potential to be $10.2 million under the tax line, have the full MLE and a sizeable traded player exception at their disposal.

Here’s how the Celtics stand in terms of TPE’s and the MLE.

Non-Taxpayer MLE = $15.049 million, per Spotrac

Georges Niang TPE = $8.2 million

Anfernee Simons TPE = $27.6 million

Chris Boucher TPE = $2.2 million

Josh Minott TPE = $2.3 million

Xavier Tillman TPE = $2.5 million

This week, we’re going to focus on the free agency market, exploring potential targets who could improve Boston’s roster.

Today, we’re starting with the guard position, specifically players whom Stevens could use the MLE to acquire.

Coby White

A quick search across social media, and it becomes clear that a lot of Celtics fans are interested in the idea of adding Coby White this summer. Boston would likely need to use their MLE to get an agreement over the line, which would hard cap the team at the first apron.

White’s age is appealing. He’s only 26 years old, so not only would he provide additional scoring and ball-handling, but he’d also fit into the idea of helping the Celtics get a little younger.

I could see a world where Boston goes with Coby White at the primary guard spot and moves Derrick White into an off-ball role, which is where he has thrived in the past. In terms of skill set, Coby White could fit into Joe Mazzulla’s system while also appeasing Brad Stevens’ desire for some additional rim pressure.

Over the past three seasons, White has used 30% of his offensive looks within four feet of the rim, ranking him around the 25th percentile of all guards in the NBA. That’s enough frequency to add a new dimension to the Celtics approach. Still, he’s also averaging around 45% of his offensive frequency coming from deep, which would keep Mazzulla happy.

In terms of accuracy, White is shooting near 65% at the cup, which isn’t great, but is enough to give him some gravity on drives. His three-point rate has been in the 37% region. I can only imagine that with Boston’s spacing and the presence of Jayson Tatum and Jaylen Brown, White’s scoring averages could improve due to the quality of shots he would be getting.

At 6’5, White has solid size for his position. He’s a slightly below-average defender, but the Celtics have had success improving guys on that side of the ball, and with some slight tweaks, he could become a league-average contributor on that side of the rock.

During the loss to the Philadelphia 76ers, it became clear the Celtics needed another ball-handler who could create their own shot, knock down looks off the catch and test a defense. White fills all of those needs.

Ayo Dosunmu

Another ‘get slightly younger’ option. I had hoped the Celtics would move for Ayo Dosunmu at the trade deadline, and now, I’m right back here just a few months later thinking about the exact same thing.

One important note here is that during his post-trade-deadline run with the Minnesota Timberwolves, Dosunmu shone in a lower-usage role. I point this out because that’s a similar role to what he would have in Boston. It’s nice to see he’s already shown an ability to produce in that type of situation.

I love how much Dosunmu likes to pressure the rim, too. He’s sitting in the mid-to-high 40s for rim-frequency in recent years, making him an ideal addition to Stevens’ desire for some extra interior pressure. However, it’s worth noting that Dosunmu has ranked in the bottom 20-ish percent of guards for three-point frequency throughout his career.

Just because Dosunmu isn’t firing up threes at volume doesn’t mean he isn’t a capable shooter. He just wrapped up a season shooting 43.9% from deep on 4.1 attempts per game. I’d imagine he’s going for quality of shot over quantity. And in terms of success at the rim, he’s similar to White, sitting in the mid-60% range.

The question is: Would Dosunmu be open to taking his foot off the break and shooting more threes? Or would Mazzulla be open to leaning into his downhill spray style offense, drawing defenders ahead of the kick-out and choosing his spots on when to shoot/look to score?

Like Coby White, Dosunmu is 6’5. He’s a slightly better defender, often sitting around a league-average Defensive Estimated Plus-Minus. For an additional guard, he can give you a bit of everything, while also giving you a little something different (downhill play).

Wouldn’t be a bad pick-up. However, Boston would likely need to go into their MLE to bring him back to the Eastern Conference.

Quentin Grimes

Quentin Grimes is coming off a solid season with the Philadelphia 76ers. At 26 years old, he’s still got some room to improve his game before entering his prime. Unlike White and Dosunmu, Grimes is a two-guard, which could make him a less attractive prospect to Stevens — and for anyone thinking he’s more of a wing, 66% of his career minutes have come at the two.

However, in terms of roster fit, Grimes could slot into the starting lineup or the bench unit. He’s capable of operating as a ball-handler, catch threat, or a hybrid of both.

This past season was the first time Grimes committed to getting downhill, with 35% of his offense coming around the rim. He has, though, been a reliable perimeter presence (in terms of volume) over his career. What I like is that after landing in Detroit, his long mid-range began to trend upward, showing he’d become more comfortable attacking close-outs.

In terms of accuracy, Grimes can be a little patchy. He’s coming off his worst season on the perimeter, hitting just 34% of his non-garbage-time threes. He did, however, shooting 69% at the rim.

Grimes isn’t a swashbuckling flame-thrower like White or Dosunmu. He’s going to attack lanes, punish gaps, and force rotations. There’s value in that for sure, the only question I have is how much that gels with what Mazzulla asks of his guards — especially as his career 2.3 dimes (3.3 this past season) don’t scream creator, either.

Like the other names on this list so far, Grimes is slightly below league average on the defensive end. There’s scope for him to become an average defender within Boston’s system.

The upside with Grimes is that it’s unlikely he will eat up the full MLE. He’s certainly not my first choice, but if he’s available and the Celtics strike out on some other options (listed above and below), he would be a decent addition.

Anfernee Simons

The name on everyone’s lips.

Let’s be real, we all knew Anfernee Simons could be flipped at the trade deadline. Coming into the season, it felt inevitable. Yet, some excellent production off Boston’s bench meant that when that trade became a reality, most of us were already dreaming up ways to bring him back in the offseason.

Simons is a proven commodity within Mazzulla’s system. We know what we would be getting.

The issue is — as with most of the guards on this list — it’s hard to see how things play out if Pritchard remains in a sixth man role.

“The reason that Payton Pritchard and Simons were able to coexist this past season was that Pritchard was starting, and then Simons was coming off the bench,” I said in yesterday’s podcast. “Obviously, there was an argument to start Simons and have Pritchard off the bench, but the point was they weren’t sharing the bench at the same time. Now, if the Celtics do go out and pick up an Anfernee Simons or a Coby White, and they’re not intending on having Prichard or whoever they pick up moving into that starting five, it makes it a lot more difficult to see how Prichard is going to sign an extension when he’s basically sharing the floor with a ready-made replacement.”

I’ll be honest, though, this is a good problem to have. If Mazzulla is comfortable running a backcourt of Derrick White and Simons, with Pritchard coming off the bench, the Celtics will have plenty of firepower at the guard positions.

Is it worth the trade-off defensively? Time would tell, but we can’t act like Simons didn’t show improvements on that end during his stint with the Celtics.

If Boston does look to use the MLE to plug the gap at the guard position, Simons will likely be the first name they check in with. After all, the fans love him, his offensive output fits the system, and you can see a world where he thrives next to Derrick White.

Whether he’s a starting point-guard on a championship team is a totally different question, which is why I keep coming back to how his addition, now that Jayson Tatum is back healthy, would impact Pritchard…

Collin Sexton

The final name on this list.

Collin Sexton, 27, has a ton of experience as a starting-level guard in the NBA, having started 357 of his 475 regular-season games. He’s had seasons where he’s shown the capability of a secondary creator, with a career year in dimes in 2023-24, averaging 4.9.

If Boston is looking for a downhill guard, Sexton could be their best bet. He’s ranked in the top-20% of guards for rim frequency since his sophomore season, with one blip during his final year in Utah. One thing that Sexton also brings that makes him unique to this list is his short mid-range game (floaters, push shots, etc), which has been a healthy part of his shot diet throughout his career.

The only knock, and this is more system-based than skill set, is that Sexton hasn’t had a single season where he’s been a high-volume shooter from deep. He’s like Dosunmu in that sense, preferring to pick his shots rather than taking a spray-and-pray approach.

That approach to his threes has allowed Sexton to be a near-40% shooter over most of his career so far. He’s not jacking them up, but he’s hitting the ones he does take at an optimal clip.

Interestingly, despite his heavy downhill approach, Sexton’s finishing around the rim has been patchy. Yet, with the spacing on offer with the Celtics, it’s fair to assume he could easily find a level of consistency that forces defenses into tough choices. I actually think he could emerge as a key scorer in Boston’s system just because of the way he’d bend defenses when they’re trying to limit attempts further up the floor.

If you look at Sexton’s accuracy across every position throughout his career, he’s shooting:

• 62.3% at the rim

• 43% across the mid-range

• 38.1% on total three-point attempts

Those numbers have come on a rebuilding Cleveland Cavaliers and Utah Jazz roster. I’d hazard a guess that they’d all improve with the level of talent the Celtics could put around him.

At 6’3, Sexton hasn’t been a lockdown defender during his career. In fact, according to Dunks And Threes, he’s only been league average in two seasons so far. The encouraging part is that one of those two came this season. Pair Sexton with Derrick White, and maybe he gets a third and fourth season in the coming years.

I like Sexton as a potential fit for Boston. He could be a solid use of the MLE, while giving Stevens the additional interior scoring he wants, while still making sense for the Celtics ’ three-point heavy system.

Ranking this list

If I were to put these five guards in order, my wishlist would look like this:

1 - Ayo Dosunmu

2 - Collin Sexton

3 - Anfernee Simons

4 - Coby White

5 - Quentin Grimes

How would you rank this list? Did I miss anyone?

Next, we look at potential wing targets in free agency.