Philadelphia 76ers: Is the third time the charm for Haywood Highsmith?

Haywood Highsmith is one of those are NBA players who actually started out his career with a G-League tryout.

A three-year starter for the Wheeling Jesuit Cardinals, which is a real team that plays at a real college in West Virginia, Highsmith didn’t receive a ton of interest coming out of college despite averaging 22 points and 12.5 rebounds a game during his senior season in the Mountain East Conference.

Had Highsmith settled for the rejection of going undrafted once his college eligibility was over, he’d surely be on to another career off the court, but instead, he took part in an open tryout for the (second) closest team to his Baltimore, Maryland home, the Philadelphia 76ers, and impressed the team enough to earn a two-way contract with the team alongside former Notre Dame point guard Demetrius Jackson.

While Highsmith only lasted roughly six months with the Sixers, scoring nine points over five games of action, he was signed to an Exhibit 10 contract and played for the Delaware Blue Coats for the 2019-20 NBA season, where he averaged 10.4 points and 6.7 rebounds in 26.6 minutes of action a night.

Now, if that was the end of the line for Highsmith on the peripherals of the NBA, he, again, would have had a nice story and a decent nest egg from which to transition into the second phase of his life, but after spending 2020-21 with the Crailsheim Merlins of the Basketball Bundesliga, the pride of Archbishop Curley is back yet again for a third tenure with the team in four years, again on an Exhibit 10 contract.

But will the third time be the charm for Haywood Highsmith and the Philadelphia 76ers? Or will he once again have to find a new basketball team outside of the City of Brotherly Love – or Delaware – to continue on with his professional career?

Haywood Highsmith has a tough road to make the Philadelphia 76ers’ roster.

Alright, let’s get this out of the way right from the jump: There is almost no real path for Haywood Highsmith to actually make the Philadelphia 76ers 15 man roster.

What, you may ask, is the almost scenario? Well, in theory, the Sixers could agree to a trade that ships, say, Ben Simmons, Shake Milton, and Jaden Springer to the Portland Trail Blazers for a two-player package of, say, CJ McCollum and Nassir Little, but even in that scenario, it feels far more likely that the team could target a veteran free agent, or even one of their two two-way contract players like Grant Riller or Aaron Henry over giving the nod to Highsmith.

With that being said, there’s clearly something about Highsmith’s game that the Sixers seem to like, as they’ve brought him into the fray on three separate occasions, even after handing over the player personnel duties to Daryl Morey.

Who knows, maybe Highsmith is just one of Elton Brand‘s guys. Even with Morey now the head honcho of the basketball operations department, Brand is still technically listed as the team’s GM and has at least some power in the department. If he wants to keep Highsmith in the Sixers’ oeuvre moving forward, what better way than to get him into camp, have him learn Doc Rivers’ scheme, and hope he impresses enough to make things interesting down the stretch?

If that happens and the team’s roster remains full at the end of camp, Highsmith could end up spending his season back with the Delaware Blue Coats, with a nice little financial bonus in his pocket thanks to his Exhibit 10 deal.

Ideal? Not for Highsmith, but remaining in the organization certainly isn’t the worst-case scenario, as he could be a trade, injury, or release away from being on another two-way contract or a 10-day contract.

If that happens, the ball would quite literally be in Highsmith’s court to prove his worth on the court.

Regardless of how things shake out for Haywood Highsmith in training camp, his story is one Philadelphia 76ers fans should know and appreciate. It’s not every day that a player makes good on a G-League tryout, let alone parlays such an opportunity into a two-way contract and two more Exhibit 10 contracts with the team.