By Matthew Geagan, CBS Boston

BOSTON (CBS) — The NBA Draft is less than two weeks away, and the Celtics are trying frantically to pawn off their three first-round picks. In no way, shape or form can Boston add three more young players to its roster, so Danny Ainge is trying to trade cash those picks in for either a higher lottery selection or potentially even a veteran that can help the young C’s of the present.

Those efforts have not been going very well, according to The Ringer’s Kevin O’Connor. Teams aren’t really lining up to take picks nos. 14, 26 and 30 from Ainge, and who could blame them? It’s a relatively weak draft class, meaning Ainge will likely have to pawn off those picks one by one. If he’s lucky, maybe a team will take two of the picks off his hands, but he probably won’t get anywhere close to what he desires on the trade market.

Chances are Ainge will have to make at least one pick for the present Celtics, make a draft-and-stash pick with with one of the two latter picks, and hope that someone will want to pop back into the first round and offer up a future pick. For the first time in a long time, Ainge does not have a future first-round selection in his back pocket, and that has to be driving him crazier than a two-for-one deal at Chipotle.

But if Ainge does have to make three picks, it won’t be the first time he’s done so. Ainge has made three first-round picks twice in his time with the Celtics, with one of those times working out extremely well. The other time… not so much.

Sure, Ainge hit on one of the three players that second time around. Danny Ainge the Blue Jays infielder would be envious of that .333 batting average, but Danny Ainge the GM swung and missed pretty badly on those two other picks. Given that it happened recently, it doesn’t instill much confidence should Ainge have to make three more first-round picks this year.

What does this mean for this year’s NBA Draft? Nothing. Absolutely nothing. But we’re going to look back anyways, because looking ahead right now is a scary proposition at the moment.

– When the Celtics had three first-round picks in 2016:

No. 3: Jaylen Brown
No. 16: Guerschon Yabusele
No. 23: Ante Zizic

Jaylen was drafted with one of Ainge’s prized Brooklyn picks, and he’s worked out pretty well for Boston. Brown has gotten better in each of his four NBA seasons and should have made the All-Star team last year. He’s a valuable piece to the Celtics and one that will be in Boston for a while, after Ainge locked Brown up with a four-year, $115 extension last October. Some cried that it was too much money for a guy who isn’t a No. 1 scorer, but Brown will be a bargain in a few years time. He’s a fabulous two-way player and it seems like the sky is the limit for the young wing.

Despite some draft-night trepidation over the selection, Jaylen Brown was a really good pick. After that though, the 2016 draft wasn’t a very good night for Ainge and company.

The Yabusele pick was one that Ainge acquired when he sent Rajon Rondo to Dallas in 2014. While “The Dancing Bear” brought plenty of upside to the Celtics, he never lived up to that potential. There was much more surrounding the fascination behind Yabu and his… rather large behind, than his actual play on the floor. He never came close to the hype as the “French Draymond” and was waived before the 2019 season.

It was a big miss when you see that Caris LeVert, who averaged 18 points per game for the Nets last season, went four picks after Yabusele.

Zizic was also a miss at No. 23, a promising international big man who never played a game for the Celtics. He was dealt to the Cavaliers in the Kyrie Irving trade ahead of the 2017 season, and went on to play 113 games for Cleveland over three seasons. He is now playing in the Israeli League.

Late first-round picks are usually flyers anyways, but Zizic is a gigantic miss when you see that Pascal Siakam went four picks later, and Dejonte Murray was drafted six picks after the big man.

– When the Celtics had three first-round picks in 2004:

No. 15: Al Jefferson
No. 24: Delonte West
No. 25: Tony Allen

Ainge had a trio of first-round picks in his second draft with the C’s, and they turned into his best draft class with the team.

Jefferson was a solid NBA big man for 14 years, though he did most of his work away from Boston after being the centerpiece of the Kevin Garnett swap in 2007. But for a few seasons, it looked like Big Al could be a solid building block for the Celtics, good enough that Ainge was able to pry KG away from his old pal Kevin McHale.

Imagine the horror if Robert Swift had slipped to No. 15. (Shutters) Let’s move on.

Snagging Delonte and Tony Allen with back-to-back picks worked out great for the Celtics. West battled injuries for his three years in Boston but was a solid player for the C’s as either the team’s starting point guard or the first guard off the bench. He was eventually traded to Seattle in the move that brought Ray Allen to Boston.

Tony Allen made the biggest impact of the three on the Celtics, playing an integral part of the team’s 2008 championship run. Allen was one of the team’s best defenders off the bench, and when it wasn’t Paul Pierce, TA was the one draped all over Kobe Bryant for long stretches in the Finals. The fact that he had the C’s championship ring fitted for his pinky makes Tony Allen a true legend.

Allen played six seasons with the Celtics before earning a huge payday from the Memphis. He fit right in with the “Grit and Grind” Grizzlies and cemented himself as one of the best defensive players in the NBA.

– Just For Fun…

The Celtics also had three first-round picks in 2001, though Ainge was not the man in charge. These picks were up to Chris Wallace and Red Auerbach, and unfortunately, this draft is remembered for one of Red’s biggest misses.

Boston had picks nos. 10, 11 and 21. They hit on No. 10 with Joe Johnson, though he was traded to the Phoenix Suns just 48 games into his rookie season in a move that brought Tony Delk and Rodney Rogers to Boston. It was a win-now move by the Celtics that backfired in a big way. Delk and Rodgers helped the Celtics have some modest success, but Johnson enjoyed a 17-year career as a prolific shooter and scorer.

At No. 11, the Celtics missed big with Kedrick Brown. Really big. Brown was extremely athletic heading into the NBA, but he couldn’t shoot. Or pass. Or rebound. Or play defense. He played just 101 games in his three seasons with the Celtics before he was cast off to Cleveland in the 2003 trade that brought Ricky Davis to Boston.

Boston passed on players like Richard Jefferson, Zach Randolph and Gerald Wallace in order to draft Brown. Oof.

Unfortunately they missed big at No. 21 as well, with Red hand-picking UNC swingman Joe Forte. He played in just 25 games in the NBA, and only eight of those were for the Celtics.

No, not a very good pick. Not when Tony Parker — whom the Celtics were reportedly high on and came ohsoclose to drafting — went with the final selection of the first round.

– What about when Ainge had TWO first-round picks???

Let’s get back to Danny. He’s had a pair of first-round picks during his run with the Celtics, and he’s done… Okay. It’s been good, but not great.

In his first draft with the C’s in 2003 (back when I was merely an intern in the WBZ Sports office, warming up cookies for Steve Burton), Ainge pulled off a draft-night swaparoo with his two first-round picks, turning Troy Bell and Dahntay Jones into Marcus Banks (miss) and Kendrick Perkins (hit).

It took nearly a decade for Ainge to get multiple first-round picks again, and he was a bit rusty when it happened. With picks nos. 21 and 22 in 2012, Ainge drafted Jared Sullinger (miss that could have been a hit) and Fab Melo (a giant bust, may he rest in peace). Sullinger had his moments when healthy, but he struggled to stay in shape and was not re-signed in 2016. Melo spent the majority of his career running into doorframes in the G League and played just six games for Boston.

At least Ainge had a mixed bag in 2014, drafting Marcus Smart at No. 6 overall and James Young at No. 17. Smart has been a hit, serving as the heartbeat of the Celtics since he first donned the jersey, while Young was another first-round bust.

Ainge had two first-round picks in 2015 as well, drafting Terry Rozier at No. 16 and R.J. Hunter at No. 28. Rozier was the definition of boom or bust. He either gave the Celtics a legit option at point guard off the bench/a solid injury replacement for when Kyrie Irving was out, or he was a total disaster on the floor. He played some solid defense and could light up the scoreboard at home, but couldn’t buy a shot on the road. He was let go when it came time for him to receive a new contract, part of the sign-and-trade that brought Kemba Walker to Boston.

Hunter, a sharpshooter out of Georgia State, never did much of anything and was gone after playing in 36 games as a rookie, though he was brought back for one game during the 2018-19 season.

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