The Boston Celtics 2018-19 season is over following the 4-1 loss to the Milwaukee Bucks. Eyes now turn to the offseason and a lot of “what if?” scenarios. We’ll break a bunch of those down here on CelticsBlog starting next week. But in the more immediate, a handful of questions have arisen about option deadlines, the NBA Draft Lottery, etc. Here are the key dates to keep an eye on for the Celtics leading into free agency.

Tuesday May 14th - 2019 NBA Draft Lottery

While it’s nowhere near as fun to see where the ping pong balls landed while still anticipating Celtics playoff games, this is still a pretty important lottery for Boston. Currently, the Celtics have the following picks:

-#14 (via the Sacramento Kings)

-#20 (via the Los Angeles Clippers)

-#22 (Boston’s own)

-#51 (Boston’s own)

While 20, 22 and 51 are locked in, Boston still has eyes on two spots. First is at 14 with the Kings pick. It would take the leprechauns and some really good shamrock work for that pick to jump up in the lottery. But even that is fraught with some peril. Let’s say the reveal starts and the Celtics (via the Kings) aren’t the first placard held up. That means Boston either got lucky or really, really unlucky. Remember, the Celtics get the pick if it lands at 2, 3, 4 or 14. If that pick jumps all the way to #1 overall, it goes to the Philadelphia 76ers and Boston gets Philadelphia’s pick at 24 instead. So, cross your fingers and hope for the best!

Beyond that, you are hoping if anyone from 9-14 does move up, that the jump is also paired with the Memphis Grizzlies moving up as well. Otherwise, the Grizzlies pick will drop from its current spot at 8 to 9 or later. That would put it out of the protected range and would give Boston a fourth first round selection. Normally, that would be great, but this draft is pretty shallow. It’s best if the Memphis pick carries over another year as an unknown and more valuable trade chip.

Thursday June 13th - Player Option deadlines for Kyrie Irving and Aron Baynes

It’s a foregone conclusion that Kyrie Irving will opt out of his contract for 2019-20 to hit free agency. It’s been that way since Boston acquired him from the Cleveland Cavaliers almost two years ago. That doesn’t mean Irving is a lock to leave the Celtics. It’s just a smart business decision to “secure the bag” as the kids say. Irving won’t opt out early, as players always protect themselves in case of some unforeseen catastrophe, but he will for sure opt out on 6/13.

Aron Baynes is in a different boat. He’s found a home in Boston and genuinely seems to love being a Celtic. As a backup/fringe starter at the center position, there isn’t likely to be a huge market for his services as a free agent. If he opts in, he’ll have a guaranteed $5.5 million for 2019-20. But Baynes is a smart guy. If he sees that there are going to be major changes, or his role is going to be drastically reduced, he may choose to head elsewhere. This is certainly a deadline to keep an eye on.

Tuesday June 18th - Player Option deadline for Al Horford

Less than a week after Irving and Baynes have to make a call on opting in or out, Al Horford needs to do the same. He said following the Game 5 loss to the Bucks that he wants to be in Boston, and there is no reason to believe otherwise. In addition, the Celtics would love to have him back. The question is more one of “One year for $30.1 million or multiple years at a lower average annual value?” Horford is on the decline at his age, but it’s a pretty slow one so far. He’s got the game and brains to stay productive as an NBA player for at least another three seasons.

The best guess here is that Horford, like Baynes, weighs the situation. If it looks like Boston is heading in a different direction, he might just opt in for the one year. If it looks like the Celtics intend to continue chasing championships in the immediate future, Horford could re-up for a few years, while also knocking some money off this year’s cap.

One last thing to note: If Horford does opt in, it would be with the understanding that he’s going to be in Boston next season. It is highly unlikely he would opt in to be part of a trade package this summer. That is a conversation Horford and his representatives will have with Danny Ainge long before a decision is made.

Thursday June 20th - 2019 NBA Draft

We’ll keep this one short. Boston will have 4-5 picks at the draft and will be active with those selections. Without saying it outright, Ainge said that adding four rookies isn’t something the team would do. Expect the Celtics to look to trade picks, either to move up the draft board or for future selections. Barring that, they’ll stash at least one player overseas for a year.

And we’d be remiss if we didn’t at least mention the possibility that Ainge could be using those picks to draft for someone else. Say his friend David Griffin of the New Orleans Pelicans, if they had worked out some pre-arranged trade for a certain big man that couldn’t be executed until the league year flipped over in early-July.

The Celtics have four restricted free agents (six counting Two-Way players P.J. Dozier and R.J. Hunter, but that’s a very different situation), with Terry Rozier and Daniel Theis being the key ones. For roster flexibility reasons, the Celtics probably won’t extend a qualifying offer to either Brad Wanamaker or Jonathan Gibson. Both players would likely just sign the QO, and that would be for more money than Boston would want to pay either player. They can always bring them back on league minimum deals as unrestricted free agents.

As for Rozier, he’s in one of the toughest spots of all Celtics free agents. In many ways, his value to the team and his willingness to stay is directly tied to that of Irving. If Irving leaves, Rozier could re-sign and move back into the starting lineup, where he performed fairly well in 2017-18. If Irving stays, Rozier could look for bigger and better opportunities elsewhere. Expect Boston to extend a qualifying offer, if only to keep their options open for matching an offer sheet or for signing and trading Rozier.

Theis will also get a qualifying offer. If he signs it, he’s on the books for one year at $1.8 million. That’s chump change for a player of his value. If he doesn’t sign the QO, Boston still retains team control. Given his backup status, the contract offers Theis will get are unlikely to be all that high. He’s a guy who probably has more value to the Celtics than on the open market. Expect him to be back in Boston next year.

Monday July 1st - Semi Ojeleye’s contract becomes fully guaranteed

This one is pretty easy. Boston will guarantee Semi Ojeleye’s contract. It’s for just $1.6 million and he’s shown more than enough promise to be worth that. It’s not a guarantee Ojeleye sticks with the Celtics, as he could be used in a trade package over the summer, but he’s not going to be waived prior to his guarantee date.

Monday July 1st - 2019-20 league year begins and free agency opens

Let’s keep this one simple. Everything is going to change. One way or another. For the Celtics and the NBA as a whole. 45% of NBA players are scheduled to hit free agency this summer. This includes potentially Baynes, Gibson, Horford, Irving, Marcus Morris, Rozier, Theis and Wanamaker from the Celtics.

Almost half the league has enough cap space to add one maximum salary free agent and still have plenty of spending power beyond that. The chessboard for the NBA, and the Boston Celtics, is going to look a lot different when all is said and done this offseason.