After making blockbuster Aroldis Chapman deal last year, how aggressive will Cubs be at this trade deadline?

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The New York Yankees operated in an ideal seller’s market last summer, beginning with the iconic team with the 108-year championship drought, a stash of young blue-chip talent and a front office that’s never afraid to think big.

Cubs president Theo Epstein put it this way after making the blockbuster deal for Aroldis Chapman: “If not now, when?”

The Cubs wanted the parade down Michigan Avenue and got maybe one of the largest gatherings in human history, generations of fans flooding the streets of Chicago last November and spilling into Grant Park. 

For a moment late Friday afternoon, Chapman stood alone on the Wrigley Field mound after beating Javier Baez with a 100.4-mph fastball. That helpless foul tip ended New York’s 3-2 comeback win over the Cubs, another reminder of Chapman’s intimidating presence on the day he got his World Series ring, a Rage Against the Machine tribute on the video board and hugs from his ex-teammates.

What about the trade deadline now that the Cubs are no longer on the greatest quest in professional sports?

“I don’t think the urgency changes,” general manager Jed Hoyer said. “The goal is to win every year. I do think that the team last year – their play almost demanded us to be aggressive. We came out from Day 1 and we played like the best team in baseball.

“We were pitching well, hitting well, blowing people out and felt like that team had one Achilles’ heel – the back of the bullpen. And given where we knew we were going in the playoffs, we needed that guy.”

The resurgent Yankees (18-9) were down to their last strike when Brett Gardner blasted a Hector Rondon slider into the right-field patio deck for a three-run homer, but that moment didn’t necessarily reveal deeper issues within the bullpen.     

Wade Davis – zero runs through 13-plus innings and 7-for-7 in save chances as a Cub – had already worked three days in a row. Rondon, a one-time 30-save closer, entered the ninth inning with a 1.59 ERA. Pedro Strop screamed and punched the air after striking out Aaron Judge looking at a slider to end the eighth inning. Carl Edwards Jr. (0.69 ERA) continues to look like someone who could handle that Andrew Miller hybrid role.

“I don’t want to say forced our hand (last year),” Hoyer said, “but with the way they played it was clear that this was a team to be really aggressive for. I think every year you have to feel that out. You have to get a sense of your club.

“Obviously, it’s too early to have a sense of this club. But last year, give them credit, they went 25-6 out of the gate and they made it really clear this was a year to be aggressive.”

The Cubs are 16-13 and leading a division that doesn’t have any other superpowers and playing in a National League that doesn’t look quite as intimidating with the New York Mets and San Francisco Giants already in damage-control mode.

On Cinco de Mayo, it’s impossible to say exactly what the Cubs will need by July 31. But the Cubs conserved resources for that deadline and also have a pretty good idea of what their everyday lineup will look like through the 2021 season, which made elite prospect Gleyber Torres available in the Chapman deal and means someone like Ian Happ could be dangled in a trade for pitching.  

With Jake Arrieta and John Lackey positioned to become free agents after this season – and Brett Anderson taking a 6.23 ERA into Saturday night’s start against the Yankees – the Cubs could be looking at a 60-percent turnover rate for their 2018 rotation.

“You can’t get in a cycle where you’re always doing something for rentals,” Hoyer said. “But at the same time, every season is sacred and you only have (so many chances). There are going to be years where things don’t come together, you have injuries, another team runs away with it. That’s going to happen. So when you know you’re in a good position, (go for it).”

That’s why Torres – who entered his age-20 season as Baseball America’s No. 5 prospect – could become a star in New York and the Cubs will never have any regrets about that 4-for-1 Chapman trade.

“I’m always confident in Theo and Jed,” manager Joe Maddon said. “We gave up a lot. The kid we gave up is very good. However, to win a World Series, I think you do it like 11 out of 10 times.”

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