The Celtics have been the offseason darling team for the entirety of last decade. With giving up Paul Pierce and Kevin Garnett, they took control of the Brooklyn Nets draft stock and held a number of chips.

Lots of picks were found to be successful: Jayson Tatum, Jaylen Brown and Marcus Smart to name a few.

They even managed to find luck in free agency, landing Al Horford a few years back and Gordon Hayward in the same offseason.

Boston even found an all-NBA player in a trade when they managed to snag Kyrie Irving.

These days, Horford walked, Hayward has been riddled with injury and left for Charlotte and Kyrie (ironically enough) is in Brooklyn.

But Boston still held a ton of cards in their draft pool, as well as convincing All-Star Kemba Walker to sign with them this past off season.

So, what gives? With so many assets on hand and success in the free agent marketplace, what could be going wrong for Boston?

A failed 2020 NBA Draft

The Celtics came into this draft with three first round picks and one second round pick.

Their first two picks were spent on Aaron Nesmith and Payton Pritchard.

Nesmith is a shooter’s shooter. For such a modern NBA league that thrives off of the three-ball, Nesmith seems like the ideal fit for any roster.

At Vanderbilt in his sophomore season, Nesmith was hitting over four three point field goals per game while averaging 23 points. Scoring is no problem for him.

There is a huge problem with him on the defensive end and he will have to significantly improve if he wants to earn minutes among the Celtics wings.

Pritchard seemed like a little bit more of a head scratcher of a pick. Some analysts had him projected as a second rounder, and he is lacking in upside.

He was a consensus All-American last year, but he is a four year senior and will be 23 in this upcoming NBA season.

With how different the NBA can be, Pritchard will have to hope to adjust fast to the new pace of the league if he wants to see any minutes.

If he is any good, he could take some of the Brad Wannamaker minutes as the third guard off of the bench, but with so many picks and so little roster space, it would have been nice to see more upside.

How does Boston stack up now in an improved Eastern Conference?

The Celtics have been one of the premier Eastern Conference teams in the last couple of seasons. Just about every team in the East has improved this off season.

The Nets will have Durant and Kyrie back and healthy, and could still possibly add James Harden.

Milwaukee, as the reigning number one seed, just replaced Eric Bledsoe with Jrue Holiday.

Miami will be returning the majority of its roster, and their young players like Herro and Robinson now have Finals experience.

Over in Philadelphia, the 76ers have a new head coach in Doc Rivers, and acquired Danny Green and Seth Curry. These two will add some much needed shooting to their roster.

Toronto will keep most of its roster most likely and continue to play at a high level with Nick Nurse heading their team.

The point in all of this is that Boston has not done much to make themselves better than this past season.

With the sudden departure of Gordon Hayward, Boston loses that asset all together, and signed two role players in Tristan Thompson and Jeff Teague.

Thompson could be just the kind of dirty-work player that they need for rebounding, but they will be staring at a much harder road to The Finals this season.

Sure, Tatum and Brown will continue to grow into the budding stars that they are, but without a big splash in the draft or in free agency, it could be a long season for Brad Stevens and this Celtics team.