With the Cubs facing a pivotal winter, we’re tackling the biggest questions facing Jed Hoyer’s front office. Reporters Bruce Levine and Tony Andracki provide their perspective.

Next up:

Should Ian Happ be the leadoff hitter in 2021 or is that an area the Cubs need to address this winter?

BRUCE

Looking for more contact at the top of the order is something Hoyer has talked about. A different type of player — the Tommy La Stella types out there, people like that who put the ball in play more often and walk a little bit more. In the case of Happ, I think he’d be fine there. He did a good job last year, but if you notice the last two or three weeks, there was a swing-and-miss factor that was a little bit troubling. You probably want somebody that makes more contact. Because Happ has a lot of power in his bat, he’d probably be best served a little further down in the order. I think he can do the job leading off if that’s what they ask him to do.

Don’t rule out a trade bringing in somebody like that, a young player who is very close to the big-league level that can be popped right in there and say, ‘hey, go for it. It’s your job to lose.’ Certainly we’ve seen every other Chicago Cubs player over the last two years try that leadoff spot and not too many other than Anthony Rizzo and maybe to a certain extent Happ find any success.

Is it time to bring in a little bit more speed and have the ’80s and ’90s leadoff man available to them? Even like what Dexter Fowler was for them in ’15 and ’16.

TONY

Yeah, I’m a huge fan of stolen bases and speed and what that brings to baseball. I’m always in favor of seeing more of that in the game today. In general, I think the Cubs do have the potential to get more athletic. A guy like Nico Hoerner — if he plays 150 or so games next year — definitely brings that element. We saw it a little bit as he started to work with Will Venable on baserunning, stealing a couple bases in a game against the Tigers. He brings that element, but that’s certainly something they could bring in from the outside as well.

I think Happ could provide that stolen-base threat as well — he has good speed and he’s shown good instincts baserunning. I don’t think leadoff is anywhere near as big of an issue this winter as it has been the last couple years, basically ever since Fowler left.

Happ can do the job, so they have an internal candidate in place. But it’s also something where they could upgrade. They could find another option like a La Stella, like Bruce mentioned. A guy who makes a lot of contact, sees a lot of pitches, gets on base and doesn’t necessarily have as much of that swing-and-miss factor where three or four pitches into the game, you have a strike out on the board. Happ has proven he can do the job, but it’s also somewhere they have the flexibility to add a guy and maybe change up the complexion of their lineup that way.

Earlier this year, Kris Bryant joked the leadoff spot in Chicago is cursed. I don’t know if we would go that far, but there definitely is a mental component of that. Happ has proven he’s able to find success even amid that. It will be interesting to see how it plays out and how Hoyer and the rest of the Cubs front office looks at the leadoff spot long-term.

David Ross acknowledged that as of right now, he is planning on heading into 2021 with Happ as the Cubs’ leadoff hitter.