That's the question Bulls fans immediately started pondering when it was revealed last Friday night that Hamilton was leaving the Detroit Pistons. It surely remains the questions on most fans' minds as they see the news that Hamilton will indeed play for the Bulls this season. Is the former All-Star enough of an upgrade at the two guard position to push the Bulls past the Miami Heat? In the end, that's really the question Hamilton's signing should be able to answer over the next four months.
Keith Bogans started every game for the Bulls last season and the team managed to advance to the Eastern Conference finals. Sure, Bogans only played 18 minutes a game. He was hardly the only player at fault for the Bulls' season ending against the Heat. Still, the reality is the Bulls made it within a few floundering fourth quarters of an NBA Finals appearance with limited production from whomever was playing next to Derrick Rose.
In that regard, Hamilton is a sizable upgrade.
Up until last season, he averaged between 18-20 points a game for close to a decade. He has always had a deadly midrange jumper. And although last year he had issues in the Pistons' locker room, specifically with former head coach John Kuester, by most accounts Hamilton should be a solid veteran presence behind the scenes in Chicago.
"I've known Rip since I was 14 years old," Bulls forward Luol Deng said during media day on Sunday. "Rip played college basketball with my brother. I used to go up to UConn, just to work out with those guys.
"One thing I can say about Rip is, all his teammates like him. I think if Rip was to come here, he'd be a great guy in the locker room. A great teammate; you know that from the guys from Detroit. They love playing with him and he's a guy who won a championship. He's been there, he knows what it takes, and I'm sure if he was to join us, I believe he would make us better."
He also has one thing Bulls' players will be in awe of from the moment he sets foot in Chicago -- a championship ring.
"He's done something that nobody on this team had [done] and went to the Finals a couple of times and won a championship," Rose told ESPNChicago.com Tuesday night. "If anything, his experience is definitely going to help us with this team."
So what's the downside as far as Hamilton goes?
For starters, he will be 34 in February. He has missed 77 games the past three years because of various injuries. He's also struggled from beyond the 3-point arc at several points through his career. He's a 35 percent shooter from distance in his career.
Again, though, let's be clear: He is an upgrade. There were nights last season when teams would leave Bogans open, daring him to make shots, so they could put more of a focus on Rose.
Plus, if the Bulls want someone who can stretch the floor, they can also put Kyle Korver into the game. Hamilton has made a career out of running through screens and hitting jumpers. He'll be asked to do the same in Tom Thibodeau's system now. Of course, he'll also be asked play defense. While Hamilton has never been known as a lock-down defender, he can certainly hold his own when needed. He'll also be asked to be a leader to a room full of veterans who look up to him because of his championship ring.
Another key to keep in mind is that Hamilton's signing probably puts even more pressure on Carlos Boozer. Boozer endured a lot of criticism last season because of his lack of production at various points, especially in the playoffs. He suffered through several injuries and struggled to find consistency later in the year.
Plenty of critics were harsh on Boozer, but they still blamed the Bulls' a majority of the Bulls' shortcomings on the fact that Rose didn't have much help in the form of a consistent two-guard who could score when needed. Now that Hamilton is in the fold, if Boozer continues to struggle, he will take even more blame than he did a season ago.
Time will tell if Hamilton's acquisition pushes the Bulls past Miami. As Rose, Thibodeau and plenty of others have expressed the past few weeks, everyone on the Bulls must improve in order to win a championship. The only thing that's clear on this day is that with Hamilton in the fold, the Bulls are closer to accomplishing their goals than they were yesterday.