The UCLA coach regrets this not just because he will lose a veteran leader and an unselfish, steady point guard who is averaging 8.3 assists a game, third-highest in the nation.
No, Howland regrets this also because he knows the fifth-year senior would have played for him much longer than one season if not for a mistake Howland said he made years ago.
"I take full responsibility for him not being here as a freshman," Howland said Monday, a day before the Bruins (7-3) face Long Beach State (4-6) at Pauley Pavilion.
"Because if I had been more patient during the recruiting process, at the end of the day, he would've come here."
Growing up in Encino, Drew attended UCLA basketball camps, watched its games and dreamed of being a Bruin.
But when Howland offered a scholarship while Drew was starring at Woodland Hills Taft, the coach added he wanted a commitment in roughly one week.
"But I didn't really want to do that," Drew said.
"I just wanted to keep my options open and weigh everything out, even though UCLA was my favorite."
Drew also wanted to "experience the whole recruiting process," according to his father, Larry Drew Sr.
In the end, Howland's scholarship offer came off the table and Drew ended up in North Carolina, a place he said he "never really liked" and one he left after 21/2 seasons.
Upon exiting Chapel Hill, Drew said the first coach to call was Howland, who apologized for his recruitment to UCLA.
"He let me know he wanted me to come back," Drew said.
Howland also spoke with Drew Sr., who coaches the Atlanta Hawks.
"To me, it takes a special man to admit he handled the situation the wrong way," Drew Sr. said in an interview.
"And [Howland] said, 'Big Larry, I owe you an apology, because I handled that situation the wrong way.' "
Drew ultimately came to Westwood, though much later than he imagined. He sat out last season because of transfer rules.
"I definitely would've come here out of [high school], maybe if he would've given me a couple of days or so after that week," Drew said. "But I don't really regret much. I just try to learn from my experience."
Drew said he and Howland are on good terms about what happened, but that neither has talked about it much publicly.
"I'm glad he finally said something," Drew said, when informed of Howland's comments during an interview.
"It's not like I was waiting on it …" Drew said, his voice trailing off.
"OK, well, maybe I was waiting on it," he said, laughing.
For so long, Drew sugarcoated his experience in Chapel Hill, where he said he simply didn't feel comfortable.
When people asked why he chose to play for the Tar Heels, he answered he did so for the tradition or the coach or the great teammates he would have, but none of that that was true.
"I never really wanted to go there," Drew said.
But he kept the truth inside — until now.
"I've always wondered when I could tell people," he said.
At North Carolina, Drew started 53 games but lost his starting job to a freshman after a 20-point loss. He came off the bench for four games and then left without saying a word.
But at UCLA, Drew is home and happy, and his assist/turnover ratio (4.9) is the seventh-best in Division I, a stark difference for a player who committed 120 turnovers as a sophomore at North Carolina, earning him the nickname "Turnover Jesus."
"He's confident in every move he makes, every pass he makes, every shot he takes. It shows," said forward Travis Wear, who also transferred from North Carolina to UCLA.
Drew is the lone senior on a team laden with freshman stars, and he has had to learn to be a leader, but Shabazz Muhammad said Drew has excelled in that area.
"He's always leading us into the locker room and telling us what our game plan is in the first and second half," Muhammad said. "That's big time. We're really feeding off that."
And Howland is glad to finally have Drew, but he wishes that he hadn't asked for a commitment so early, because maybe he could have had Drew for four seasons instead of one.
"It's all on me," Howland said. "I regret it to this moment."