Does a team have to be above .500 before it can decide to buy at the trade deadline?

That idea seems simple enough. The object of baseball — and any other sport, really — is to win more games than you lose. The more you do that, the better your chances are of making the playoffs. And if you make the playoffs, of course you better your chances of winning a title.

But the Cubs are currently in a weird situation. While they haven’t had a .500 record at the end of a day since May 12, they remain very much in the National League Central race a few weeks away from the Aug. 1 deadline. They’re in a different spot than, say, the Red Sox, who actually ended Thursday only two games below .500 (40-42) yet are 15 games back and in last place in the American League East. Regardless of their record, the Cubs are certainly not out of the hunt for a division title.

“You’re in contention if you’re in contention,” Cubs manager David Ross said Tuesday, prior to the beginning of the series against the Phillies. “The record doesn’t matter, right? We’re three games back. I don’t care if you’re 20 games over .500 or you’re 20 games below .500 — three games back from the people leading your division, you’re three games back. That’s the way I look at it.”

Of course, since Ross said that, the Cubs went and got swept by Philadelphia. The gut punch came in the series finale Thursday night. Despite a seven-inning, three-run effort from Kyle Hendricks, the Cubs only managed one run (a pair of ill-advised bunts from Nick Madrigal and Christopher Morel and a failure to capitalize on errors by Phillies outfielders were major contributing factors) in the 3-1 loss.

Nick Madrigal and Christopher Morel’s bunts weren’t calls that came from the bench.

Cubs manager David Ross discusses the two plays: pic.twitter.com/qJ1eDj1sbL

— Ryan Herrera (@ryan_a_herrera) June 30, 2023

After getting swept in Anaheim and falling a season-low 10 games under .500, the Cubs won 11 of their ensuing 13 games and moved within a game of breaking even. Since then, though, they’ve dropped four straight — and yet, while they ended Thursday 37-42 and in fourth place, they’re still only five games back of both the Reds and Brewers at the top of the Central.

“The focus is on winning the division and being the best version of ourselves and continuing to improve,” Nico Hoerner said. “We’re obviously fortunate that we’re [five] games under .500 and in the division race. That’s not true in every division, but there’s nothing to be ashamed of for making the most of that.”

Not that the Cubs should be satisfied just being in the race.

Again, you want to win more games than you lose. Being under .500, regardless of the division standings, means you aren’t doing that. Everyone in the organization — from the front office to the coaches to the players — understands that. It shouldn’t be acceptable that they’re just in the hunt, especially when they’re now riding a four-game losing streak.

“I don’t think that we would ever, from an organizational standpoint, say having a losing record is good enough,” Cubs general manager Carter Hawkins said. “I think given where our division is right now, the fact that we are where we are, there’s still encouraging things in the future for us. But I don’t think any of us look at our record and say, ‘Hey, we’re below .500, and that’s OK.’ I don’t know that .500 is the magic win percentage, necessarily, but I do think that we should win more than we lose.”

Unless a drastic turnaround happens, it would be tough to say right now that the Cubs should push all of their chips in and try to make a run. As Hawkins pointed out, there isn’t “much history of teams that are under .500 that have a huge chance of winning the World Series.”

Of course, the 2021 Braves were only one game better than the Cubs at this point in their season, and they bought leading up to the deadline before going on to win the World Series. Still, as Hawkins also pointed out, they didn’t push all of their chips in then, either. They acquired players to build solid depth (i.e. Joc Pederson, Eddie Rosario, Jorge Soler, Adam Duvall), but they didn’t make a huge splash.

The Cubs also aren’t likely to make a huge splash right now. Maybe they can make similarly smaller decisions to acquire players to help the playoff push (maybe another left-handed reliever?), but at this point, it appears the moves wouldn’t be made in hopes of making a World Series run.

So, if buying is the direction they end up taking, the front office will weigh its options as far what moves make the most sense for the team now and for the future.

“There’s a lot of different ways to skin the cat,” Hawkins said. “We’ll certainly explore all of those and try to make sure we’re factoring in all the information we can.”

It will likely be at least a few more weeks before there’s a clear indication on what the Cubs will do at the deadline. Again, they’re five games under .500 and five games out of the division. Similar to how the cold streak from late June to early July sunk their 2021 season, a hot stretch over these last 10 games before the All-Star break could very much sway the front office to make additions to the roster. That’s still a realistic scenario.

It was only last week that Cubs chairman Tom Ricketts told fans in London, “Obviously we’re buyers right now,” as reported by the Chicago Tribune’s Meghan Montemurro. With the NL Central being the way it is, this losing streak likely hasn’t changed that.

The way Hawkins said he and president of baseball operations Jed Hoyer are approaching the deadline direction is by “really just looking at the team, looking at how many wins we’re hoping to get this year and in future years and make a decision from that standpoint.”

In another division or in another year, making the decision to deal some major league assets would probably be more likely. But in this division this year, it’s not out of the question that a Cubs team below .500 but still in the fight could actually buy at the deadline (though a string of wins would give the front office a little more comfort in going that direction).

“I think at the end of the day, you’re making a decision around this year’s playoff odds and future years’ playoff odds,” Hawkins said. “Certainly, the exact record that you have doesn’t really matter if you get it down to that granular level. But from a heuristic standpoint, it just doesn’t feel very comfortable being under .500 and saying, ‘Hey, we’re in a super competitive position.’ We definitely think team has got a chance to be well above that, and we’ll work towards that every day.