Strickland was reclassified as a shooting guard his senior year and enrolled at UNC as a member of the third-ranked recruiting class in the country in 2009, joining John Henson, Leslie McDonald and David and Travis Wear.
Roy Williams gambled and played both Strickland and Henson out of position in 2009-10 – the former at point guard, the latter on the wing – and their struggles coincided with UNC's only NIT run during the Williams era.
Strickland switched back to his natural position during his sophomore year, stepping into Marcus Ginyard's vacant spot, but adapting to the college game still presented challenges.
In the fourth game of the season, against Vanderbilt in the Puerto Rico Tip-Off, Strickland was benched due to ineffectiveness.
"I took Dexter out for a long stretch there," Williams said following the 72-65 loss. "… You can't have one assist and four turnovers. You cannot hurt your team. You've got to play better."
While his offensive game prompted questions even then about his starting role – Strickland averaged 6.2 points on 37.4 percent shooting during ACC play – his defensive play stood out on the perimeter. UNC finished the 2010-11 season strong, winning 17 of 19 before dropping a 76-69 decision to Kentucky in the Elite Eight.
Wildcats point guard Brandon Knight led all scorers with 22 points, but needed 18 shots to reach that total.
"I still remember the Kentucky Elite Eight game and I said at that time I don't know that I've ever had a guard play a better game defensively as two-man than Dexter did," Williams said on Friday.
It seemed as though, after two years of searching for his niche, Strickland had crafted his role alongside Kendall Marshall in UNC's backcourt.
Through the first 19 games of his junior season, Strickland averaged 7.5 points on 57.0 percent shooting. His offensive efficiency exploded as he thrived in transition and slashing in the halfcourt, while he emerged as UNC's defensive stopper out front.
Then, on Jan. 19, 2012, Strickland's right knee buckled on a drive to the basket in the second half of UNC's win at Virginia Tech. The medical verdict was a torn ACL, forcing the junior to miss another run to the Elite Eight.
Strickland's offseason rehab progressed as expected and he was cleared to return to action on Aug. 27. He expected to start at point guard following Marshall's early defection to the NBA, which prompted an awkward scene at UNC's media day on Oct. 11.
Williams told reporters that freshman Marcus Paige would likely be the starting point guard only moments after Strickland offered that he wanted to fill Marshall's role.
Strickland admitted that he wasn't back to full health at the time and it was evident throughout the early part of the season. His defensive ability was impaired as his once-superior lateral quickness seemingly vanished.
North Carolina's inexperienced lineup struggled to excel in transition, while Strickland's lack of trust in his right knee hampered his ability to drive in the halfcourt offense, forcing far too many jump shots that missed their target.
"I'm not a shooter; that's not my game," Strickland told InsideCarolina.com last month. "But I had to adjust to it because I couldn't move as fast on offense and I couldn't move as fast on defense, so I couldn't play defense to my ability."
Strickland averaged just 4.9 points on 31.5 percent shooting through UNC's first 10 ACC games this season, prompting fans and media to question why the senior guard was starting over sophomore guard P.J. Hairston.
Following UNC's 87-61 debacle at Miami on Feb. 9, Williams finally altered his lineup, although not in the way that anyone expected. Hairston entered, but Strickland remained.
What followed has been a rebirth of sorts. With improved spacing on the perimeter and in the paint, Strickland is averaging 9.6 points on 53.2 percent shooting over his last seven games.
Most impressive, however, has been Strickland's ability to take care of the ball. Through UNC's first 24 games, the 6-foot-3, 185-pound guard posted a solid 2.76 assist-turnover ratio (91 assists, 33 turnovers).
In his last six games, however, Strickland has turned in a staggering 10.3:1 assist-turnover ratio with 31 assists against just three turnovers. Those are statistics that even the nation's top point guard prospect would never be expected to deliver.
"I just focus on not turning the ball over," Strickland said. "Thirty-one assists are easy because Reggie [Bullock], Leslie and P.J. [Hairston] are making shots. It's just easy with the lineup that we have because it spreads out the floor even more and enables me to drive to the basket."
The lineup change has also coincided with steady progress in overcoming lingering challenges following his knee injury.
"It's been getting better each and every game," Strickland said. "Right now, I'm 100 percent with my knee, and as far as confidence goes, it's at an all-time high."
On Saturday, Strickland will be the lone member of UNC's five-man 2009 recruiting class to be honored on Senior Night. The Wear twins transferred following the 2009-10 season to UCLA, Henson was drafted 14th overall by Milwaukee in June and McDonald will play one more season after sitting out 2011-12 with a torn ACL.
"It feels different," Strickland said. "The only person that's been here with me is Leslie, and he got hurt unfortunately. But as far as everybody else leaving – the [Wear] twins and John going to the NBA – I feel like I'm by myself, but I'm happy to be here on the team. I love my teammates all the same."
Paige has benefitted from Strickland's guidance probably more than anyone else on UNC's roster.
"He's been through it all and he's helped me a lot to get through some of my struggles this year," Paige said. "… He's allowed me to play my game alongside of him. He's been a great senior leader, so hopefully we can get a win for him [on Saturday]."
Strickland's resiliency in the wake of injury and criticism has been greeted with unforeseen success as his senior season draws to a close.
"He's a tough kid," Williams said. "He's handled some tough times. He's really done some good things and I'm really pleased lately that things have gone a little bit smoother for him."
North Carolina's regular season finale against Duke will represent Strickland's 123rd career game, his 90th start and his last home game at the Smith Center.
There's still hope for more games to play, though. As the Tar Heels are trending upward, so to is Strickland in the final days of his UNC career.