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Celtics Mailbag: Jrue Holiday extension, trade hypotheticals

The Celtics have come out of the All-Star Break riding a seven-game winning streak, putting Brad Stevens in a great spot to take his time with the buyout market while getting a look at new trade additions Xavier Tillman and Jaden Springer this week. Let’s jump into some questions about the rosy outlook that lies ahead for this group as they try to secure the top spot in the East sooner than than later. If you have questions about the Celtics or NBA, email brobb@masslive.com or tweet @briantrobb

Hey Brobb,

If Brad successfully traded Brogdon for Porzingis, do you think he has the balls to trade Smart for Holiday? The optics of it would be a whole lot different for the fans and it would maybe be more of a slap in the face for Marcus to trade him for a guy he is compared to a lot (especially when people were hating on him for winning DPOY). —Cheers, Joel

I don’t think the optics would have held the Celtics back from making such a move. The fact that the team was able to pivot to the Smart move with the Grizzlies once the Brogdon trade fell through indicates that was a discussion that didn’t come together out of nowhere. The team has certainly had discussions with other squads about him for years before this summer but there was clear hesitation to make a move before that point. The equation I think changed with the way the postseason went last year. Boston’s weaknesses were exposed and the team had a clear surplus in the backcourt with Derrick White looking like he was underused with the most upside about the group. Brad Stevens knows he has a tight window to win with this core while its affordable so any option to upgrade the roster was in play.






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Why didn’t Celts make a strong push for Galo. He’s healthy, was here last year, can shoot the lights out, good insurance for Hauser? — Josh B

Not surprised at all the Celtics weren’t in the mix for him. He’s not moving around well at all defensively coming off his ACL tear and that would put a target on his back any time he’s on the floor in the postseason. He’s also not exactly shooting the lights out this season (35 percent from 3) which is a big downgrade from the likes of Sam Hauser. The Bucks bench has left a lot to be desired this year o it makes sense for them to roll thence on a 35-year-old Gallinari. The Celtics are in a far better spot with their second unit so they are better off looking for someone a little more defensive-minded to fill that final roster spot.

If you could cover any other NBA team which would you pick? — Walt F

Great question. I think I go with the Warriors. It’s always been a team I’ve sought out as a neutral observer since it’s just a fun brand of basketball to watch (up until this year at least). Throw in a committed fanbase and plenty of intriguing storylines for the present and the future and that checks the boxes for me as a beat writer.

How much does Jrue want to get in an extension? — Kevin OB

He should be asking for the max at least initially. Whether that’s realistic for the 33-year-old is entirely another matter. His market is going to be a fascinating subplot to watch during the tail end of this season. There’s little doubt the two sides will talk extension when they can before the end of the regular season. However, Holiday could have a pretty good market this summer with the lack of big names on the free agent market this summer. A few teams are hoarding a big amount of cap room that could put some pressure on Boston if Holiday isn’t willing to give a discount for a couple more years of added security tacked onto the deal. If the Celtics end up winning a title, I expect ownership to pay up and deal with the fallout down the line (likely a couple cost cutting trades). Otherwise, tough decisions may have to be made this summer.

Hello Brian. How deep does the playoff rotation go? What do you think the extensions for White & Holiday will be like? How many wins do you think they’ll get? Which matchups in the playoffs do you prefer they face? Any experimenting on offense or defense you think Joe should try? — Truth

I don’t expect Joe Mazzulla to go beyond eight players deep in the playoffs most nights. Payton Pritchard and Sam Hauser should get shots at some action in at least the first half of the early rounds but beyond foul trouble or injuries it’s tough to envision him going any deeper than that. Extension for Boston’s backcourt will likely be dependent on the postseason. I’d bet the Celtics get something done with Holiday while White ultimately gets to free agency. Give me 65 wins for the regular season and I’d imagine Boston would be pleased not having to play Miami as an opening round foe. Outside of that, there probably wouldn’t be much concern for any potential opponent early on.

Hi Brian,

I love our defensive backcourt with Derrick and Jrue but if they had any weakness it’d be against smaller quicker guards like Maxey and Brunson. Do you see Springer getting a shot or will Joe keep a short playoff rotation? Thanks. — Andy

Don’t think Springer will be much of a factor this season. He could get some chances in regular season games particularly as the team starts to rest up after clinching the East. However, his youth and offensive limitations make it hard to imagine him getting a chance within this loaded rotation. Ultimately, this was a trade that was more about the future than the present for Boston. They had a TPE that was set to expire and Springer is making a very modest salary ($4 million) next year and still has developmental upside. He’s good defensive depth at the end of the bench for now but don’t anticipate Joe Mazzulla using it unless injuries force him into action.

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