The short answer? A lot. We're not here for short answers, though. There's quite a few factors to consider in the mix, ranging from what the actual state of Kawhi Leonard's health actually is, and how it's likely to hold up in the future. The issue of the actual nature of his relationship with the San Antonio Spurs organization is also very murky right now, with completely opposite reports coming from various sources.
Future contention windows on a team surviving as a fringe contender in Kawhi's absence almost exclusively on the otherworldly coaching abilities of Gregg Popovich also have to be factoring into whatever decision tree may be unfolding in Leonard's, Pop's, and GM R.C. Buford's noggins, as must the eventual necessity of Pop's retirement. Will he slog through another retooling? It's becoming quite possible Leonard has already decided he will not.
On the other end, one has to ask whether the Boston Celtics can muster a trade deal they'd be willing to part with; the Spurs are a notoriously conservative organization when it comes to trade, and much like Danny Ainge, rarely make a move if there's not a good chance of "winning" a deal, content to cycle through their own draft picks and system. But, as noted in the video above, the Celts are one of very few teams that really could mount an offer good enough to land Kawhi. The question really boils down to what Boston would offer for a healthy Leonard, as Yahoo Sports' Chris Mannix points out they've already demonstrated a willingness to gamble on converting a player once on board.
What do you think a fair deal would be? Without an extension, but healthy, I'm not sure I could stomach a deal likely to be accepted, even if Ainge can. I'd be willing to entertain a trade involving Jaylen Brown, Marcus Morris, Guerschon Yabusele, Semi Ojeleye, Abdel Nader and whoever we select with this year's first-round draft pick, though I'd really rather wait until mid-season to see how Leonard has healed and Jaylen, Yabu and Semi have developed. Even though several analysts - including a few in the video above - believe it will take Jayson Tatum to get Kawhi, I'm going to have to agree with Tommy Heinsohn: