The rest of his selections have been, well, questionable.
Grant and his staff have never shied away from reaching for "their guy," regardless of where many mock drafts expected them to go.
In their last three rebuilding years, the Cavs have come away with six first-round picks, including four in the top four overall. This kind of draft ammunition had Cleveland thinking playoffs this season, although they're off to just an 11-23 start.
Blame can be passed around to plenty of different areas, although no one should be feeling more heat than Grant.
Hindsight is 20/20, which is exactly why we're revisiting who he drafted and if they were in fact the correct pick.
Is this unfair to do? Totally, but it's also fun (and perhaps a bit sad) to see what could have been.
2011 draft, first and fourth overall picks
Grant's first draft was without a doubt his best.
He picked up an additional first-rounder from the Los Angeles Clippers in return for agreeing to take Baron Davis' contract off their hands. This unprotected pick would, by some miracle, end up falling first overall. Cleveland also had the fourth overall pick to show for a 19-63 season.
Kyrie Irving was obviously the right pick.
Analysis over and moving on.
The Pick: Tristan Thompson, fourth overall
Available: Jonas Valanciunas, Klay Thompson, Kawhi Leonard
Best Option: There's some talent beginning to establish itself from this class, but it's hard to argue with Thompson. He's a great rebounder, has made tremendous strides offensively and is probably the hardest working player on the team.
Thompson is averaging 11.9 points and 9.8 rebounds a night, and has started every game at power forward for the Cavs this season. Valanciunas had to go through a buyout with his Lithuanian team and didn't join the Toronto Raptors until a year later. The Cavs tried acquiring a third pick in the 2011 draft to get Klay Thompson, who's averaging 19.3 points for the Golden State Warriors this season. Leonard has been a solid role player for the San Antonio Spurs, chipping in 11.5 points and 6.1 boards a night.
Some of these other picks are tempting, but Thompson is just 22 and already one of the top rebounders in the league. Grant got this draft right.
2012 draft, fourth and 17th overall picks
Grant again worked the trade wire, sending the 24th, 33rd and 34th overall picks to the Dallas Mavericks for Tyler Zeller at No. 17.
The question is, who could they have drafted instead?
First let's start with the fourth overall pick, Dion Waiters.
The Pick: Dion Waiters, fourth overall
Available: Harrison Barnes, Andre Drummond
Best Option: Waiters was a surprise pick for the Cavs, as many feel they reached heavily on the Syracuse guard.
Cleveland needed a small forward or shooting guard from this draft, someone besides Kyrie Irving who could score the ball. While Waiters has been dynamite off the bench lately, one has to wonder what the future holds for him. Attitude is a question, as is concentration, as it seems Waiters either steps out of bounds or gets called for a travel or carry at least once a game.
Irving and Waiters have proven to be very inefficient when on the court together, something you hate to see from your two franchise cornerstones.
Andre Drummond has been great for the Detroit Pistons, but the Cavs didn't need two offensive projects with limited post games. Pairing him with Tristan Thompson would have been a bad fit.
The best pick would have been Harrison Barnes.
Barnes is averaging 11.7 points and 4.0 rebounds for the Warriors this season, which may not seem like much compared to Waiters' 15.3 points a night.
Looking at the makeup of the team, however, Barnes would have been the best fit next to Irving. He's always been at his best next to a strong point guard, and the numbers this season tell us just that. While playing next to Stephen Curry, Barnes' points, rebounds and field-goal percentage all increase dramatically (per NBA.com/Stats). In 15 games as a starter this season, Barnes is averaging 14.3 points, 4.7 rebounds and shooting 38.6 percent from deep.
Barnes is a better three-point shooter than Waiters and would have thrived as a floor-spacer and scorer next to Irving.
The Pick: Tyler Zeller, 17th overall
Available: Jared Sullinger, Draymond Green
Best Option: Zeller is an OK pick here, especially with the lack of depth the Cavaliers have at center.
In fantasy redrafts though, we don't go for just OK.
Sullinger would have been a great big man to bring off the bench. He's averaging 13.4 points and 7.3 rebounds in just 26.9 minutes a game for the Boston Celtics. Durability is a concern, but with Thompson eating the majority of his minutes at power forward, Cleveland could have limited his workload.
Zeller will also turn 24 on January 17, and doesn't possess nearly as much upside as the 21-year-old Sullinger.
The Cavs would have been better off taking the former Ohio State star.
2013 draft, first and 19th overall picks
Grant picked up the extra first-rounder this season from the Miami Heat thanks to the sign-and-trade of LeBron James. The Cavs were then able to swap first-rounders with the Los Angeles Lakers thanks to a clause in a deal for Ramon Sessions the year before.
The Pick: Anthony Bennett, first overall
Available: Victor Oladipo, Ben McLemore, Nerlens Noel
Best Option: This is the pick that may cost Grant his job. Bennett has been terrible this season, and has actually regressed over the past few weeks.
To be fair, this has been one of the worst draft classes in recent memory. Michael Carter-Williams and Trey Burke have been good, but the Cavs were never going to take either of them with Irving already at point guard.
Had the Cavs taken Barnes instead of Waiters the year before, they would be in the market for a shooting guard this draft. Oladipo and McLemore both present a lot of upside, with the best fit for Cleveland being Oladipo.
This season for the Orlando Magic, Oladipo is averaging 12.8 points, 4.3 rebounds and 3.5 assists. He's an athletic playmaker on the wing who can handle the ball when necessary. Oladipo is also an excellent defender who would fit well in Mike Brown's defensive system.
Bennett could still turn out to have a solid career, but right now he's too much of a project on a team that wants to win now. Oladipo was the most NBA ready and should have been the pick.
The Pick: Sergey Karasev, 19th overall
Available: Tim Hardaway Jr., Nate Wolters, Jeff Withey
Best Option: Karasev doesn't see the court very often, so it's tough to tell if this was the best pick or not right now.
Others drafted behind him have been producing for respective teams, however. Hardaway Jr. is averaging 8.6 points off the bench for the New York Knicks while shooting 41.7 percent from deep.
Wolters would have been a solid combo guard off the bench, and is averaging 6.3 points and 3.4 assists for the Milwaukee Bucks this season. Withey hasn't seen much playing time for the New Orleans Pelicans, but is a 7-foot shot-blocker Cleveland could have used had they passed on Zeller.
Right now, the best pick looks like it would have been Hardaway Jr. He's been one of the bright spots for the Knicks this season with his scoring off the bench and deadly outside shooting.
Final Revised Roster
Given the draft pick changes, here's what the Cavaliers' depth chart could have looked like.
|Position||Starter||2nd String||3rd String|
|Point Guard||Kyrie Irving||Jarrett Jack||Matthew Dellavedova|
|Shooting Guard||Victor Oladipo*||Tim Hardaway Jr.*||Carrick Felix|
|Small Forward||Harrison Barnes*||C.J. Miles||Alonzo Gee|
|Power Forward||Tristan Thompson||Jared Sullinger*||Earl Clark|
|Center||Anderson Varejao||Andrew Bynum||Henry Sims|
*denotes change in draft pick
Compared to what the Cavs have now, the overall level of talent has gone way up. Irving finds a lot more offensive weapons around him, and Waiters' bench scoring has been made up for by Miles, Hardaway Jr. and Sullinger.
Players who are forced into starting duty now (Clark, Miles) could comfortably come off the bench and play against inferior competition. Bynum still remains a strong trade chip, so there's room to improve even this roster.
Now, it will be years before we know for sure if Grant made the right picks or not.
So far, it's not looking good.
All stats via basketball-reference.com unless otherwise noted.