Risks and Rewards for top-5 all-time Celtics trades

The mentor/student duo of Red Auerbach and Danny Ainge have pulled off some beauties over the years, and here are the candidates for biggest haul-via-trade that the Celtics have ever made, with risk - reward ratings (1-10) on each.

The 2017 pick-swap with Philadelphia 76'ers/ Risk: 3/ Reward: 7 (for now - still to be determined)
Granted, the value of this one is yet to be determined, but this trade needs to be in the running. Boston traded places with the 76'ers and ended up with the third pick, thereby yielding the number-one pick to Philly. The 76'ers grabbed Markelle Fultz with the first overall pick, and Boston took Jayson Tatum at #3. The Fultz-Tatum comparison is still in limbo, but after one full season, Jayson wins hands-down thus far - and the Celtics have a potential 2019 lottery pick via the trade. If Zion Williamson or R. J. Barrett end up in Boston via the 2019 NBA draft, the Reward number jumps to at least a nine.

Kevin Garnett and Ray Allen for ten players, two first-round picks and cash Risk: 3/ Reward: 8
This comes down to actually two trades in the 2007 off-season. This one certainly turned things around for Boston. The risk was low due to Kevin's super-stardom prior to the trade. Think of it. Thirteen commodities from the Celtics to Minnesota and Seattle for three players (Big Baby Davis also came to Boston). With the Big-3 of Paul Pierce, Allen and Garnett, the Celtics won the Championship in 2008. Had Garnett come to the Celtics a few years earlier, the reward would increase.

Kevin McHale and Robert Parish for two first-round draft picks Risk: 4/ Reward: 8
This Auerbach move was similar to Danny Ainge's pick-swap in 2017. Boston swapped picks with Golden State, getting the third pick (Kevin McHale) and Robert Parish while also sending the 13th pick to the Warriors. Parish thrived as a starter for the Celtics, as did McHale, while the first pick by Golden State, Joe Barry Carroll, never set the world on fire. Red knew that drafting third, he was going to get Carroll, Darrell Griffith or McHale, but Parish's fit with the team with Dave Cowens installed as the team's center may have been in question. And I think Auerbach would have been satisfied with Griffith (who won rookie of the year), but maybe not so if Carroll fell into his lap. Robert and Kevin won three Championships.

Garnett, Pierce, Jason Terry and D. J. White to the Nets for four first-rounders Risk: 2/ Reward: 9
Danny Ainge bucked his mentor on this one. Danny was critical of Red retaining players well past their prime. So, off went Paul and Kevin to the Nets. The picks became Marcus Smart, Jaylen Brown, Jayson Tatum and Kyrie Irving (via trade of the pick to Cleveland). Pierce and Garnett are both retired, and the Celtics are poised for what some believe to be a decade-long dynasty. There was some luck involved here, and even Danny had no idea what this trade would deliver. The risk was very low, and the reward turned out to be sky-high.

Bill Russell for Ed Macauley, Cliff Hagan and the Ice Capades Risk: 8/ Reward: 10
Similar to the preceding Ainge trade where he had no idea how good those picks would be, Red could not have totally realized just how great Russ was going to be. But 11 Championships later, it became quite clear just how productive this move was. Boston also picked up Tom Heinsohn and K. C. Jones in the same draft, and they were on a roll. This was a brave and innovative move by Auerbach, and the results can not be denied. Ed Macauley and Cliff Hagan were multi-season All-Stars, and even Red had to be somewhat unsure of how Russ would perform in the NBA of that era. This one gets my vote for best-ever trade by the Boston Celtics. High risk led to through-the-roof reward.

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