The Trail Blazers need a new backup shooting guard after trading Allen Crabbe to the Brooklyn Nets. Armed with an open roster spot, and lacking veteran influence, President of Basketball Operations Neil Olshey could look to a familiar face to replace Crabbe.

Gerald Henderson, only a year removed from his brief tenure in Portland, is still a free agent after parting ways with the 76ers. The 29-year-old guard started 41 games for Philadelphia last season, but was released before the final year of his two-year $18 million deal became guaranteed. Given that few teams have cap space remaining, and the Blazers' apparent need for depth at guard—a reunion has the potential to be beneficial for both sides.

The move seems obvious enough that even ESPN's Kevin Pelton brought up the subject on Tuesday:

The Blazers may hope to replace Crabbe with development from internal candidates Jake Layman and Pat Connaughton ... The Blazers also clear a roster spot here and could even dip into their taxpayer midlevel exception to sign a replacement at lower cost. A return for Gerald Henderson, who played well in Portland in 2015-16 and remains unsigned several weeks into free agency, would make sense for both sides.

The Blazers want to return to the playoffs next season, so adding a player with Henderson's experience is a better alternative than banking on the unproven Connaughton and Layman.

Henderson’s Fit in Portland

The void left behind by Crabbe is considerable. He averaged 28.5 minutes and 10.7 points per game last season, all while maintaining impressive shooting percentages. Henderson might not be able to fill those shoes completely, but he would be significantly cheaper, and does have a set of skills that can help the team

Henderson is a passable defender, a fierce attacker from the baseline, and he is a decent 3-point shooter from the corner. While in Portland, he connected on 44.4 percent of his corner 3-pointers, which is a higher rate than what Crabbe shot from the corner in 2016-17. His corner shooting dipped to 36.7 percent with the Sixers last year, but Henderson would likely recover to at least the 40-percent mark in the Blazers’ system—a milestone that he has surpassed in three out of the last four seasons.

Beyond the on-court fit, Henderson would also be returning to a team he thinks highly of. In April of 2016, Henderson shared this with Joe Freeman of The Oregonian:

"I'd love to come back here," he said. "If they want me back and we can come up with a contract that makes sense, then I'd love to come back here. This has been a great year. I was just telling the guys; this has probably been one of the most fun teams I've been on. This has been one of my most fun years. Because we've really worked for this. We've really earned this. It's a tight group, a great group of guys."

Henderson continued his praise nearly two months later during his exit interviews:

"It's been a great year. They have here, from top to bottom, a great staff, great teammates, coaching staff, training staff, everybody behind the scenes ... I can't imagine a better place than (Portland); they do things the right way. It's so hard at this point to know what's going to happen in July, but this is definitely somewhere I'd like to play."

Situations change and players often inflate their positive sentiments to curry favor from fanbases, but it appears the Henderson has legitimate admiration for the Blazers' staff and front office.

Salary Cap Concerns

Complications arise for the Blazers, however, when it comes to the luxury tax line and adding free agents.

Portland has to trim $2.9 million from its payroll to avoid the luxury tax, a point that Blazer’s Edge editor Eric Griffith outlined on Wednesday.

For the 2017-18 season, the Blazers swapped out Crabbe’s $19.3-million contract for Nicholson’s $2.8-million cap hit and reduced their payroll from $138.7 million to $122.2 million. This salary reduction lowered their current luxury tax bill from $43.1 million to $4.4 million... ...Portland also now sits only $2.9 million over the luxury tax threshold. A straightforward move—trading Ed Davis for a draft pick, for example—could take them below the tax and delay any future repeater tax penalties by a year.

The Blazers can avoid inflating their payroll by getting Henderson to agree on a veteran minimum salary. As an eight-year veteran, Henderson would receive a salary of $2.1 million, but the league would cover $857,000 of that salary as part of their program to incentivize teams to sign experienced players.

Bottom Line

Portland has yet to make a move for a veteran player this offseason, and reuniting with Henderson could work on multiple levels. The Blazers would gain a consistent presence, and Damian Lillard would see the return of a respected teammate. Competition for a playoff spot in the Western Conference will be stiff, so it’s essential the Blazers fill the hole left by Crabbe with a player who can reliably contribute immediately. Henderson fits that profile.