In his two previous season as a backup Dayton Flyers point guard, he and his team made it pretty far up that mountain. They won 49 games and made two NCAA Tournaments.
But now the Flyers have slid back down the slope and with Saturday's 78-70 loss to Penn at UD Arena, they find themselves in an unfamiliar hole.
“Yeah, we’ve got some climbing to do,” Crosby said in classic understatement.
The Flyers are 4-5. The last time the program was in that predicament was 19 seasons ago.
Until 10 days ago they were riding a 16-game winning streak at UD Arena. Now the Flyers have lost two of their last three games there.
And coming into Saturday’s game, they were 13-0 all-time against Ivy League schools.
But Penn out-shot them, out-hustled them, out-thought them.
Afterward coach Anthony Grant said the underdog Quakers had more focus and more energy than his team.
While there was plenty of blame to go around, he shouldered much of it.
“I have to look in the mirror tonight and say I didn’t do a very good job preparing our team for what we needed to do,” he said. “I got to do a better job.”
Some players the Flyers usually count on all but disappeared Saturday. Three starters — Darrell Davis, Trey Landers and Jalen Crutcher combined for 11 points on 4 for 16 shooting.
The only two guys who stood out were Josh Cunningham, who benefited from a lot of setup passes by his teammates and finished with 21 points on 9 for 9 shooting from the floor. Over the past three games he has made 22 of his 23 field-goal attempts.
The other player who had flashes of success was Crosby. He came off the bench for Crutcher and sparked the team in the first half as it overcame a 14-point deficit.
With the game on the line in the second half, he was the one player who showed some courage. He drove, he pressed the defense and he ended up with a career-high 15 points.
Unfortunately he still had a couple of costly turnovers at the end, but he was trying to make something happen.
On a day was there was nothing to smile about for the Flyers, at least you have to feel good for Crosby.
He’s traveled a bumpy road since the end of last season.
After Archie Miller seemed to lose confidence in him in the final games last season and cut his minutes, he decided to transfer. He had spent two years in Scoochie Smith’s shadow and it wasn’t certain he was ever going to see sunshine here.
Soon after he took over the UD job, Grant gave Crosby the release he asked for. The junior point guard went back to Baltimore, only to decide after a month that he wanted to return.
Grant took him back and made him a starter, then replaced him in the Nov. 29 Auburn game with the freshman Crutcher.
Crosby played just eight minutes that game and then seven at Mississippi State last Sunday. Both games the Flyers lost.
Crutcher started for the first time at Mississippi State and led the team with 18 points. He fell early in last Wednesday’s game against Tennessee Tech, limped off the court and Crosby filled in admirably for 16 minutes.
He came in off the bench again Saturday and played well enough to keep Crutcher on the sideline. He was on the floor 25 minutes to the freshman point guard’s 18.
“I’m just trying to be a boost on this team, whether it’s coming off the bench, starting, whatever they want,” Crosby said. “I’m still on this team.
“I know they’re going to need me and I think I can help the team out when I’m in the game. And if not, I’ll cheer the other guys. Whatever happens, I have full confidence in the coach.
“Right now we’re just trying to figure out a way to win and I’m on board with whatever they need. It’s a long season and I know we’ll go through some things.”
But he’s not accustomed to 4-5 and losing a non-conference game everybody expected the Flyers to win.
“It’s different,” he admitted. “I think there’s something down the road why we’re going through this. Maybe we’ll learn from thiis and when we come to the A-10 we’ll be ready. Right now though I’m not sure what the lesson is.”
Maybe he and his teammates just need to look at his arm and start climbing.