Ranking the Ainge trades: Good business (No. 15-11) - A key gamble and turning Jiri Welsch into Rajon Rondo

Danny Ainge has made 60 trades since being hired as the president of basketball operations for the Celtics in May 2003. With no basketball on the horizon until July, BSJ contributor Ryan Bernardoni and I teamed up for an enjoyable, albeit challenging endeavor: Ranking the Ainge trades from worst to best overall.

To accomplish this task, Ryan created a formula that allowed us to grade the deal based on a variety of factors (importance, quality) while also evaluating the deal at the time a trade was made and in hindsight (years later). Some deals will get the benefit of hindsight more than others in this exercise but we did our best to account for those issues. The end result is the following ranking from 60-1 with an analysis/explanation of each deal. 

We looked at part one of the series on Wednesday and some forgettable ones on Thursday, debated the Perk trade on Monday, and started diving into his good deals in Part 4. Today, we start to break down the best of the best as we edge towards the top-10.

11. Raef LaFrentz, Dan Dickau, and a 2006 first-round pick (No. 7 Randy Foye) to the Trailblazers for Theo Ratliff, Sebastian Telfair, and a 2008 second-round pick (No. 46 Trent Plaisted) (June 2006)

Ryan Bernardoni: In my opinion, this is the most interesting trade to evaluate in Ainge’s history. In the moment it looked like the C’s sold the seventh pick in the draft in order to make a bet on Sebastian Telfair and dump one future season of bad money in the form of LeFrentz’s three remaining seasons for Ratliff’s two. In that context, even before you consider that Portland was able to turn Randy Foye into Brandon Roy for nothing more than cash, the trade seems like a fire-able offense. The estimable Bob Ryan graded it an F- and he wasn’t necessarily wrong.

There’s more to the story though, and it began to reveal itself even before the draft. In the lead up, there were rumors that the Celtics were interested in Rajon Rondo and considering taking him as high as seventh if they stayed put. Teams often leak this type of information but it’s reasonable that Boston could have had Rondo in the same prospect tier as Foye and Roy. Look at any individual draft “Big Board” in any year and you’ll find players sharing a tier who ended up drafted in the 6-10 range and the 20-25 range. It’s just the way prospect evaluation works. Ainge bought back into this draft at No. 21 (for cash and a future first-round selection) and seemingly got his man. That prospect evaluation was good enough that we won’t get to ranking the move until tomorrow.

The larger context goes to comments that Ainge and Doc Rivers made that night where they talked about aligning contracts and preparing for future moves. In retrospect, it seems clear that Ainge had identified 2007 as the inflection point where they would either win the lottery after tanking, trade for a superstar (or two), or have to trade Paul Pierce and begin a longer rebuild. With that specific timeline in mind, LaFrentz was a major liability and Ratliff a potential asset, in an age where “expiring contracts” had significant value.

That combination of highly rating Rondo, understanding the team’s timeline, and knowing what was appealing on the trade market ended up being a visionary piece of business. When it came time to put together a Kevin Garnett offer it was certainly important to have developed Al Jefferson and to hold the T-Wolves own future pick. However, being able to pad the trade out with one season of Ratliff instead of the Lakers’ package that carried two seasons of Lamar Odom (who had less than zero interest in moving to Minnesota) was specifically mentioned by Kevin McHale as an important factor.

Brian and I disagreed on the rating of this trade because he gave it an average “importance” score in retrospect. I gave it the highest possible score in that metric because, without it, I think Garnett ends up a Laker. Either way, it was a huge gamble by Ainge that paid off handsomely.

12. Jiri Welsch to the Cavs for a 2007 protected first round pick (February 2005)

The Celtics initially acquired the 6-foot-7 wing as an intriguing prospect in the Antoine Walker blockbuster deal in the fall of 2004. He showed some promise out of the gate in Boston, averaging 9.2 ppg while shooting 38 percent from 3-point range as a starting shooting guard next to Paul Pierce. Welsch struggled in his second season in Green however and lost his starting job to rookie Tony Allen midway through the 2004-05 regular season. In response, Welsch told a Czech website after he retired that he actually asked for a trade from Boston in 2005, after being unhappy with his reduced playing time.

This demand was a blessing in disguise for Ainge as he managed to land a protected first-round pick for a guy who only lasted two more years in the NBA. In a classic case of diminishing returns, the Cavs shipped off Welsch after this trade deadline deal just four months later, netting just a second-round pick for him. Meanwhile, Ainge ultimately used the first-round pick acquired for the swingman in a draft night deal in 2006 to land some guy by the name of Rajon Rondo.

13. The No. 31 (Deyonta Davis) and No. 35 (Rade Zagorac) picks in the 2016 NBA Draft to the Grizzlies for a future Clippers first-round pick (No. 20 Matisse Thybulle) (June 2016)

Boston entered the 2016 NBA Draft with an absurd eight draft picks after several years of wheeling and dealing to accumulate draft assets. Ainge ultimately ended up using six of those eight picks on draft night (a mistake in hindsight) but he still avoided being squeezed on a poor return in the one draft night trade he did pull the trigger on while holding 13 percent of the picks in the draft.

Opportunistic deals are always important on draft night as teams end up willing to pay a premium in order to land an asset they like. That’s what ended up happening here with the Grizzlies, who clearly put a first-round value on a couple of players still available at the start of the second round with Boston’s picks. The Celtics probably had no interest in using these picks in all likelihood (they didn’t have the roster space for them) but they still managed to squeeze Memphis for a future first-round selection for the two selections. Davis ended up being out of the league in three years while Zagorac never made it to the NBA. Meanwhile, the C’s are still waiting to use the first-round pick acquired in this deal after flipping it on a couple of different occasions before eventually landing a future first-round pick in 2020 (Milwaukee's pick).

14. Avery Bradley and a 2019 second-round pick (No. 45 Isaiah Roby) to the Pistons for Marcus Morris (July 2017)

There was plenty of drama in the summer of 2017 once the Celtics found out they had landed Gordon Hayward in free agency. Before they could sign the prized All-Star, they needed to clear out some salary space on their roster however to make it happen. Essentially, one of Jae Crowder, Avery Bradley or Marcus Smart needed to go to make the money work and clear the cap space needed to sign Hayward to a max deal once the salary cap for the 2017-18 season was unexpectedly lowered to $99 million. That surprise decrease put the C's in a bind when it came to financial planning.

Normally, other teams demand a premium from trade partners in a situation where they know salaries need to be dumped by one squad to make a subsequent signing happen. Boston’s front office managed to negotiate proactively here, setting up a long list of scenarios for themselves that they could pull the trigger on once they got a commitment from Hayward. The big takeaway? The Celtics picked right here in moving on from Bradley, who clearly peaked in Boston in his career prior to the deal. The undersized shooting guard was entering the final year of his four-year, $32-million contract in the summer of 2017  before he was expected to command a substantial raise that the C’s weren’t going to be able to afford with all their other big-name targets. For one year of Bradley and a second-round pick, the C’s managed to nab Morris who had two more years left on his under-market deal at the time. Moving on from Bradley also opened the door for more playing time for Jaylen Brown who had shined as a rookie as a starting SG when Bradley had missed time due to injury.

It’s always a delicate balance to try to win in the present and plan for a team’s financial future in the process. The Celtics managed to do both with this transaction.

15. Jordan Crawford and Marshon Brooks to the Warriors in a three-team deal for Joel Anthony, three second-round picks (33. Jordan Mickey, 31. Deyonta Davis, 51. Ben Bentil) and cash (January 2014)

Turning nothing into something is a regular theme for Danny Ainge as we work our way higher into the teens and there may be no better example of that than here. The Celtics gave up an injured player (Leandro Barbosa) and an over-the-hill big man (Jason Collins) to land Jordan Crawford initially at the 2013 trade deadline in what was essentially a salary dump for the Wizards. While Crawford didn’t help much during that final Boston playoff run for Kevin Garnett and Paul Pierce, he did have one more year on his rookie deal as the rebuilding started under Brad Stevens in October 2013.

Crawford playing his way into a starting point guard role for the C’s under Stevens system, suddenly morphing himself into an appealing trade rental playoff teams around the NBA by January. Once the Celtics’ record went sideways in the standings, Ainge decided to sell high with Brooks while also maximizing the C’s ability to absorb a bad contract (Joel Anthony) as long as they were compensated with draft capital. The end game here turned into three second-round picks (acquired from Miami and Golden State) in a three-team swap with two of those picks being top-tier second rounders (No. 31, No. 33). Jordan Mickey did not work out as one of the picks but the C’s were able to leverage No. 31 into a first round selection last year (No. 20 overall). While one of the picks here came thanks to a salary dump, rehabbing Crawford’s value produced a prospect, not a bad return for a guy who was out of the league two years later.

Next up: The game-changers