The Cubs are always trying to stay ahead of the curve, picturing the lineup five years out, recalibrating their financial position and preparing for worst-case scenarios.
When Jon Lester made his recruiting trip to Wrigleyville in November 2014, the Cubs showed the All-Star lefty their projected defensive alignment across the diamond for 2016 — with Gold Glove outfielder Jason Heyward playing center.
Heyward would eventually sign the biggest contract in franchise history, an eight-year, $184 million commitment to a player who won’t turn 27 until August. Between that megadeal — and the guarantees to super-utility guy Ben Zobrist, veteran starter John Lackey and swingman Trevor Cahill — the Cubs lead the majors with more than $276 million spent on free agents this offseason, according to ESPN’s tracker.
The Cubs needed all the stars to align for the Plan-A offseason. President of baseball operations Theo Epstein ruled out the idea of signing two $100 million players back in November — and made it sound like that kind of offseason binge would have to wait for the new TV money to kick in first.
[MORE CUBS: Jason Heyward on 2016 Cubs: Everybody is hungry]
But this team earned the reinvestment after winning 97 games and two playoff rounds and turning Wrigley Field into a destination again. Chairman Tom Ricketts and president of business operations Crane Kenney worked with the baseball side to get creative. Plus some of the market forces that left Yoenis Cespedes unsigned in late January — and pushed the Cuban outfielder back to the New York Mets over the weekend — also drove the Cubs to think big this winter.
Cespedes, who transformed New York’s lineup after a July 31 trade from the Detroit Tigers last summer, reportedly agreed to a three-year, $75 million deal that includes an opt-out after this season, allowing him to become a headliner in a weak class of free agents.
“Next winter doesn’t look that great,” Epstein said. “(That’s) one of the reasons (why) we were aggressive this winter with bringing in the free agents that we did.”
Stephen Strasburg might never live up to the unrealistic hype with the Washington Nationals — and he’s already had Tommy John surgery — but he will be a 28-year-old free agent next winter with an All-Star/No. 1-overall-pick pedigree.
When healthy, Carlos Gomez has played Gold Glove defense in center field, stolen 40 bases and blasted 24 home runs, all in the same 2013 season. He just turned 30 and will get paid with a good walk year for the Houston Astros.
Outside of those types of premium players, “there really aren’t many talented free agents out there,” Epstein said during a recent Cubs Convention panel.
“It’s really dry, and there’s going to be a lot of demand,” Epstein said. “So as we looked at it, we realized we almost needed to do two offseasons worth of shopping in one offseason. Ownership and our business side were fantastic to work with, trying to figure out how we could strategize and structure some things financially to be aggressive now.
“I think it put us in a really good position for the next couple years. Maybe next offseason will be more active in the trade market than we are in free agency (or we do) some lower-profile free-agent signings.”
[SHOP CUBS: Get your Cubs gear right here]
Remember, payroll is always relative to where the Cubs were when the Ricketts family took over the team (around $145 million on Opening Day 2010) and the rest of a booming industry (even the Kansas City Royals will be in the range of $130 million when they defend their World Series crown).
It’s also getting harder to see where the Cubs can realistically add another core player to their everyday lineup with first baseman Anthony Rizzo (26), shortstop Addison Russell (22), third baseman Kris Bryant (24) and outfielders Jorge Soler (24 in February) and Kyle Schwarber (23 in March) already locked into place.
At the same time, the Cubs can see a two-year window to win a World Series before Cy Young Award winner Jake Arrieta becomes a free agent, Lackey probably retires and Lester starts to decline in his mid-30s. Right when all those young players will start to get expensive through the arbitration system, winning closes off access to top-of-the-draft talent and the cable bubble might burst.
Big picture: The Cubs don’t know what their next play will be in a rapidly changing media world. The franchise owns an equity stake in Comcast SportsNet Chicago, which holds exclusive cable rights through the 2019 season.
Looking for leverage, Kenney says the Cubs are “100 percent” focused on launching their own network and points to another industry-in-transition deal, how CBS Radio Chicago wouldn’t have been considered the frontrunner until swooping in with a game-changing offer that ended a long partnership with WGN-AM 720.
On some level, this is also a sign of weakness. Beyond the financial uncertainty, the Cubs “won the offseason” because the farm system doesn’t have any pitching prospects close to being part of a playoff-caliber rotation, and their young lineup got exposed by the Mets during a National League Championship Series sweep.
Against that backdrop, the Cubs took their shot this winter. And they better be right, because they might not get another chance to dramatically reshape the team next offseason.
“We’ll know we got to our goal as an organization when we’re not relying on free agency regularly,” Epstein said, “because we have almost everything covered from our farm system and internally. That may be a hard goal to accomplish. Free agency is going to help us get where we’re going. But it’s not something that we want to rely on every offseason.”