The difference this time around is the six-foot-1, 218-pounder will have a better offensive line to protect him as well as new toys at his disposal.
Although Grossman was sacked just five times, the team surrendered an NFL high 66 last season. A quarterback coming off a major knee injury needs to limit the number of hits he takes.
The Bears aren't asking Grossman to win games, but he will need to make plays for the offense not to become one-dimensional. He appeared to be on his way last year when he tore up his knee in Minnesota.
Healthy and expected to take the first snap at mini-camp next week, Grossman is anxious to prove he's not injury prone and has just run into a stretch of bad luck since being drafted by the Bears in 2003.
Behind Grossman is Chad Hutchinson, who made five starts last season.
Hutchinson is light years ahead of Jonathan Quinn, but that alone should not make the Bears feel better about the backup quarterback situation.
Quinn is out of the league and Hutchinson was in a similar spot about a year ago.
While Hutchinson has reestablished himself as an NFL quarterback, he struggled after having a career game against a poor Minnesota secondary.
In his defense, he had to deal with shuffling on the offensive line that came to a head when the Bears allowed nine sacks in the season finale against the Packers.
The Bears have gone on record that they believe Hutchinson can be a starter, but the obvious preference is to keep him in a supporting role to Grossman.
Orton is the prohibitive favorite, as the Bears spent a fourth round pick on him in last month's draft.
The Bears see him as a potential starter in the league and the team has also adopted a policy of developing a backup quarterback from within rather than signing one in free agency.
Krenzel had a 3-2 record in five starts as a rookie, but was forced into duty because of desperation as opposed to ascending to the job. He hurt his chances by not going to NFL Europe for additional work and will have a tough time making the team.
Kittner has the benefit of knowing Ron Turner's offensive system from their days together at Illinois. He spent the first half of the NFL Europe campaign as the backup, but has assumed the starting role for the Amsterdam Admiral's because of an injury.
Dinwiddie is still stuck in reserve duty for the Hamburg Sea Devils and could be a practice squad candidate.
The Bears have discussed carrying four quarterbacks the roster, but ultimately that would limit their game day roster flexibility.
In many ways the season will depend on the stability of the position. The Bears have started three quarterbacks the past three seasons and six of the last seven.
For there to be any kind of offensive continuity, Grossman will have to stay healthy and be effective.