But there was one thing that Wanamaker never got comfortable with during his first season in Boston - not playing in games.
Both have moved on to other teams, creating the kind of opportunity in Boston that Wanamaker has been longing for in the NBA.
That was among the many factors that weighed in Wanamaker's decision to re-sign with the Celtics during the offseason rather than return to Europe where he was a proven, established star whose greatest ability was to impact winning championships.
"Also, that chip on my shoulder, wanting to prove myself," Wanamaker said following the unveiling of a new basketball court and Celtics-themed room renovation to a family in Melrose as part of the Celtics, Arbella Insurance Home Makeover Series. "I want to show that I can play with this team and on this level and be a rotation guy."
That only can happen with playing time, something that Wanamaker will be fighting for next month when training camp opens.
Kemba Walker will be the team's starting point guard, with Marcus Smart either joining him in the starting backcourt or sliding over to the point from time to time.
Carsen Edwards, a second-round pick in last June's NBA draft, was a summer league sensation who is seen by many as the likely first guard off the bench for Boston.
Wanamaker, however, has other plans in mind.
"You have to come in ready from the jump, show what you can do to earn the opportunity (to play)," Wanamaker said. "If you don't show what you can do, how can they give you an opportunity?"
And to Wanamaker's credit, opportunities were few and far between last season despite him being relatively productive when he was afforded a chance to play.
Although he averaged just 9.5 minutes per game last season, Wanamaker seemingly made the most of his limited role.
The 6-foot-4 guard appeared in 36 games last season, averaging 3.9 points, 1.6 assists and 1.1 rebounds per game. He made 47.6 percent of his shots from the field, and connected on an impressive 41.0 percent from 3-point range.
While those numbers were solid relative to his playing time, Wanamaker knows he can do more.
And that opportunity appears to be now, an opportunity he expects to make the most of this season.
"Last year was a tough year for everybody on our roster," Wanamaker said. "And probably on the coaching staff. We under-achieved. This year we have to come in with a clear mind and hope that things go better."
Wanamaker added, "I see a bright upside for me here. I wanted to come back and do it again."
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Brad Wanamaker sees 'bright upside' for himself with Celtics originally appeared on NBC Sports Boston