It was an important task for the Cubs to find two new TV broadcasters once Steve Stone and Chip Caray departed after last season. Both Caray and Stone left on unpleasant terms with the organization, and Brenly and Kasper were chosen to fill their shoes.
"It's been very easy for me," Brenly admits. "Len is a guy who does a ton of homework. He's in both locker rooms before the game and he's very computer savvy. He makes it very easy for me as an analyst, because he's willing to let me do my own thing. Sometimes baseball announcers fill up every second of a game. As time has gone on, Len and I have both learned when to point out things on the field and when to simply let things play out."
A lot has changed since Brenly left the Cubs following the 1991 season to assume a role on the San Francisco Giants' coaching staff. The Cubs have hired five managers, including Dusty Baker, and assembled five winning seasons in that span.
"The expectations have certainly changed," Brenly said. "As this team has gotten better, and with some of the players that have come aboard, the fans are more demanding and the expectations are higher. It's different than it was when I was here before."
Since falling in the National League Championship Series almost two full years ago, the Cubs have been severely bitten by the injury bug. This season alone, Mark Prior, Kerry Wood, Todd Walker and Nomar Garciaparra have all been on the disabled list, so the team has once again played short-handed.
Despite losing some key weapons, many believe the Cubs still have a shot at the playoffs. But Brenly warns fans to stay realistic.
"I don't think the expectations can be too high, but you have to be realistic," said Brenly, a native of Ohio. "This team has had a lot of injuries and has been able to stay around .500 all year. Given the fact that the Cardinals have pretty much run away with the division, you have to look at the Wild Card. I'd rather have the fans expecting the team to win."
The aforementioned controversy between the broadcasters and numerous Cub players last season stemmed from critical comments from the booth on several late-season broadcasts. This season, things appear to have remained peaceful between the players and TV personalities.
In addition, Brenly makes it clear that he was never given a mandate by the team regarding his broadcasting style.
"There was nothing said in any way, shape or form from the Tribune Company, Comcast or WGN," Brenly said. "I can't say if anything was said to Len. They just said to come in here and do what you were doing as an analyst in your other jobs."
After coaching the Giants for four seasons (three of which came under Baker), Brenly joined FOX Sports to analyze games and eventually become the Diamondbacks' color commentator when the team entered the league in 1998.
After spending three seasons in the team's broadcast booth, he was hired to replace Buck Showalter as manager in 2001. Brenly's first season at the helm turned out to be a dream, as the Diamondbacks won 92 games behind ace pitchers Curt Schilling and Randy Johnson, beating the New York Yankees in the World Series.
"I'll be forever grateful for the opportunity to play, coach and ultimately manage this game," Brenly said. "From sitting in the manager's seat, I've learned that everything is not as cut and dry as it looks from the press box."
In both 2002 and 2003, Brenly led his team to winning seasons, including a playoff appearance in '02 as winners of the NL West. By the time the 2004 season began, the Diamondbacks had traded Schilling and fielded a younger team.
After getting off to a slow start, Brenly was fired near the halfway point of the season with the team's record at 29-50.
"In 2001, when I would push the buttons, they would come through more times than not," Brenly said.
"I think managers get too much credit when things go well, and get blamed too much when things go poorly," he said.
And after being away from the dugout for over a year, the former big league catcher with the Giants has gained a lot of perspective about managing.
"The best manager in the world is going to help his team win only a couple of games each season," Brenly said. "The bottom line is, you can put the players in a position (to win), but if you don't execute, you don't succeed."
With his background, Brenly knows other managerial opportunities could arise in the future. Before the season began, a few teams made contact with him, though the scenarios were not ideal, he says.
"I don't currently have any desire to go back into managing," Brenly said. "I can be very selective as to the given situation. I just don't see a good fit right now with the teams that are looking for a manager. I've already scratched that itch. Each morning I look at my World Series ring on my nightstand. I'm very content, because if I don't go on the field again as a manager, it won't bother me."
That's not to say the passion and desire to lead a team won't return to Brenly should the right organization call at a perfect time.
For now, though, the 51-year-old will settle for broadcast and production meetings as opposed to daily press conferences, injury updates, and clubhouse issues that consume every major league manager's day.
"I love the city of Chicago and going to Wrigley Field for 81 games a year," said Brenly. "At this stage in my life, it was the right move to make."