The Chicago Bulls kick off a five-game road trip on Wednesday night, their longest trip of the season. It is also their longest since 2016-17, when the team had a pair of six-gamers in November and February of that campaign. This year’s trip, however, could be better described as a gauntlet.

All five opponents are Western Conference playoff contenders. The Denver Nuggets (Jan. 17) and Golden State Warriors (Jan. 11) are the top two teams in the conference. Meanwhile, the Portland Trail Blazers (Jan. 9), Los Angeles Lakers (Jan. 15), and Utah Jazz (Jan. 12) sit seventh through ninth in the West standings.

The Bulls have already played two of these teams this season; back-to-back in fact. Both happened to be memorable affairs, but for the wrong reasons.

Chicago hosted the Warriors on Oct. 29, losing 149-124. In the process, they conceded multiple NBA records. This includes Klay Thompson‘s 14 3-pointers, 17 Warriors 3-pointers in the first half, and 92 points through the first two quarters.

Two days later, the Bulls faced the Nuggets. They put up a much more competitive effort, as the game needed to be decided in overtime. Unfortunately for the Bulls, a Paul Millsap putback with 0.1 seconds remaining secured a 108-107 victory for Denver.

However, it should be noted that both games happened when Fred Hoiberg was the coach. None of these teams have had the chance to experience Boylen Ball. In fact, only four Western Conference teams have: the Minnesota Timberwolves, Oklahoma City Thunder, Sacramento Kings, and San Antonio Spurs. This five-game trip will be a huge test for the brash brand of basketball Jim Boylen is attempting to instill.

Sadly, the Bulls offense, on paper, is too rigged and retrograde to have any sustainable results. Under Boylen, Chicago averages one of the slowest paces and the fewest 3-point attempts and potential assists per game.

Meanwhile, every opponent on this trip is a solid defensive team. The Nuggets, Lakers, and Jazz are all in the top 10 in defensive rating, while the Trail Blazers and Warriors serve as the league median. If these teams clog the paint and convert turnovers into transition opportunities, that will spell big trouble for the Bulls.

Speaking of defense, that facet was one the few silver linings of Boylen’s surreal tenure. The Bulls had the ninth-worst defensive rating in the NBA when Hoiberg was fired. Boylen came in and whipped the team into shape. Chicago closed out 2018 with the eighth-best defense in the league.

However, Boylen’s staunch defense hasn’t yet arrived in 2019. The Bulls have allowed over 110 points in all three of their games this year. The resultant 119.6 defensive rating is third-worst in the league.

This trip will show us how much Boylen is willing to adapt to the talent on his roster. It’s great that Robin Lopez can give the Bulls a reliable scoop hook on the occasional post-up. However, this team is so much more than the rugged rock pounders he wants them to be.

The Bulls are a young, athletic roster equipped with guards that can make plays and bigs that can stretch the floor. They deserve to run the floor, and take open 3-pointers, and to move the ball around to open up scoring opportunities as opposed to doing it just to see if the next guy can find a way to the basket.

Boylen has already witnessed positive results twice when he mixes his defensive-minded coaching with an offensive gameplan suited to the players’ skillsets.

Their 116-114 win on Dec. 7 over the Thunder, Boylen’s first as head coach, saw the Bulls run with Russell Westbrook and company to the tune of 107.5 possessions and 19 fastbreak points. Both numbers are the highest in a game under Boylen. Lauri Markkanen put up eight 3-point attempts and knocked down half of them, Zach LaVine went 2-of-5 from outside, and the recently-traded Justin Holiday went 4-of-6.

The Bulls even did it again in their 119-116 overtime loss on Jan. 4 to the Indiana Pacers. While the game wasn’t uptempo, players were more willing to shoot from outside than in most games.

The team attempted 28 3’s in the game, their most since the Spurs game on Dec. 15. Markkanen and LaVine attempted nine each. Chicago’s final three baskets in regulation were all 3-pointers. LaVine nearly sent the game into double-overtime with another one, but time expired and his foot was partially out of bounds.

However, games like that have been the exception more than the rule.

The Chicago Bulls kick off their longest road trip of the season on Wednesday night in Portland. There has been much debate about the merits of Jim Boylen’s new system. Considering the caliber of teams on the docket, this stretch of games could be the ultimate test to prove if his old school approach can hold up in the modern NBA.