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Danny Ainge vs. Pat Riley: Battle of Winning Culture

The Heat and Celtics will most likely be battling for the top free agents this season, who as the best odds at landing them?

NBA: Boston Celtics-Media Day David Butler II-USA TODAY Sports

This year the Celtics will be able to clear max cap space and go after some of the most coveted free agents, specifically Gordon Hayward. With the first pick and a chance to add another all-star, the Celtics are balancing throwing out a competitive roster with building a young team that can seamlessly grab the reins and become the next great team once Golden State begins to come back down to earth. A key ingredient to that plan is to actually land the big free agent. Last year, the Celtics were able to outbid other intriguing options for the services of Al Horford, and they’ll hope to do the same thing again this year.

But this off-season, the Celtics will find themselves toe-to-toe with the Miami Heat and the great Pat Riley. There’s no secret that Riley is one of the most respected GM’s in the league and once he has his eyes set on a free agent target, other suitors notice. It’s already been reported that the Celtics are strongly in the running for Gordon Hayward, but the plot has thickened as the Miami Heat are also gearing up to make a big push for Hayward as well.

All evidence is pointing to an inevitable clash between two proud organizations led by respected general managers and run by some of the best coaches in the league. So the question becomes: which franchise has the edge?

The Present

Right now there’s really not much of a competition in terms of overall roster strength. The Celtics have the best players between the two headlined by Isaiah Thomas and Al Horford, they have better young talent, they’re coming off a 53-win season, and an Eastern Conference Finals appearance. The Heat on the other hand are coming off a weird season where they started 11-30, then went on a second half run that led to them finishing the year 41-41. The Heat were led by a team of scrappy veterans and a great coach who got his veterans to buy into their system.

There has been no indication that Gordon Hayward was unhappy in Utah and that’s important. It most likely means that Hayward isn’t going to just be looking for a situation that is just different, but rather a situation where he sees a clearer path to making The Finals. As interesting as the Jazz have been, their future isn’t exactly set up for long term success. Boris Diaw, Joe Johnson, Derrick Favors, Rodney Hood, Dante Exum, and Raul Neto are all heading for pay days after next season. Furthermore, the Jazz are neither much of a draw for free agents and depending on how you feel about guys like Exum and Hood, may not have much in developing young talent. All that isn’t to say that the Jazz can’t figure out, but it’s clear that their future doesn’t exactly show a clear path to contention for years to come.

The Celtics provide that certainty thanks to their slew of promising young players and two all-star candidates. The Heat? Well they have the sway of Pat Riley who has been known to be one of the best recruiters in the game. They have one of the most respected coaches in the league, and they have Goran Dragic, Hassan Whiteside, and an upcoming lottery pick. Is that as good of a lure as Boston? Better yet, is that even as good as a roster as the Jazz? As great as Pat Riley is, he’ll need more than great beaches and tax breaks to get over that hurdle, and he just might have a trick up his sleeve.

Paul George to the Heat

Miami’s talent doesn’t necessarily stack up to either Boston or Utah right now, but one way they could close the gap is by going after and landing Paul George. Riley has been a very persuasive presence for players and despite reports about Paul George wanting to go elsewhere, there’s always a chance that if you bring George into a winning environment and you go on a deep playoff run, he’ll end up willing to stay put instead of bolting to a questionable fit in Los Angeles. The money would be tight, but they could make a trade centered around this years draft pick, Justise Winslow, and Tyler Johnson. They would then have the cap to sign Hayward to the max and fill out the roster with a bunch of minimums, it would look something like this:

Miami Heat
(*Roster tool can be found at via @dangercart)

The prospect of playing with Paul George would definitely raise the appeal of Miami, but how much? We’ve seen a team like the Warriors thrive with a strong core four and minimum guys, but that team was way more talented and had guys like Andre Igudola, Shaun Livingston, and David West who brought a stabilizing force to the rest of the team. I doubt those type of veterans bypass the allure of playing for the Warriors or Cavaliers to go to Miami. Furthermore, chances are the fit of Goran Dragic, Paul George, Gordon Hayward, and Hassan White is nowhere near as seamless of what we saw in The Bay, and once teams start attacking Whiteside in the PnR in the postseason, Miami may not have any viable backup options to keep him on the floor.

Finally there’s the issue of Paul George’s contract. Gordon Hayward’s camp most likely isn’t just going to blindly sign a long-term deal without getting some type of confirmation that Paul George will sign an extension. If that doesn’t happen, Miami probably still falls out of the running, and they’ll have to scramble to get together a strong enough team that convinces Paul George to stay.

Boston’s path

The Celtics could also go after Paul George, but there are a few drawbacks. One, they would face the same issues with getting a commitment for him long-term before they signed Hayward, and even if they signed both George and Hayward, the team could be paying a ton of taxes down the road for a squad that may or may not be better than the Cavaliers. Furthermore, the Celtics could probably still put together a stronger and better fitting roster than the Heat even without the addition of George. Here’s a quick example:


Here, Boston would lose some of their frontcourt depth and most notably Avery Bradley, but they would be able to replace that with more frontcourt presence in Richaun Holmes, Andrew Bogut, and the entrance of Ante Zizic and Guerschon Yabusele. Furthermore, they’d be adding the number one pick in the draft (Markelle Fultz), and would be getting a (hopefully) more improved Marcus Smart and Jaylen Brown. Hayward would be able to slide in seamlessly between Thomas-Crowder-Horford-Zizic, and the depth will allow them to mix and match dozens of lineups that could come in handy as Stevens mixes and matches his team during playoff matches. That’s not to mention that as Hayward gets deeper into his contract the Celtics lottery picks will continue to develop year after year. This means Hayward would be jumping into a presently strong roster that could only improve as the Celtics young talent develops.

The Verdict

This off-season will be quite interesting. Regardless of what we might think, It really all depends on what Hayward and his family will decide on what’s the best for them. That may lead him to Miami, Boston, or hey, he might decide that Utah is the best spot after all. Regardless, each spot does bring its own allures and flaws and it will be intriguing to see what Hayward ends up deciding during the off-season. With that being said, it is hard to argue against the fact that the Boston Celtics are the most equipped team for long-term and present success.

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