SAN DIEGO -- It was five years ago that the Cubs' front office celebrated the signing of left-hander Jon Lester to a team-record contract with drinks in the lobby bar at the Hilton San Diego Bayfront. It was a franchise-altering move that helped catapult Chicago to World Series glory.

It was at the start of Spring Training two seasons ago that the Cubs inked right-hander Yu Darvish to a five-year pact that was meant to help bridge the ace gap after Lester's deal expires. Add both of their contracts together ($281 million combined), and the total still does not reach the heights of the nine-year, $324 million contract free-agent Gerrit Cole agreed to with the Yankees on Tuesday night.

"The top of the starting pitching market has taken off, to say the least," Cubs president of baseball operations Theo Epstein said.

The Cubs are in the market for rotation help this winter, but they were never going to be climbing to the top of the free-agent ladder. That said, there is always a trickle-down effect when available pitchers start coming off the board. And that is not limited to the likes of Cole or Stephen Strasburg -- the latter signing a seven-year, $245 million deal with the Nationals that was a record for a pitcher for one whole day.

With $77.5 million tied up in their rotation right now (including starting candidate Tyler Chatwood) and a payroll already projected in the neighborhood of $200 million-plus, the Cubs are seeing what might be out there in the lower rungs of the open market. At these Winter Meetings, there have been a few agreements that helped establish some sense of cost:

RHP Tanner Roark: Two years and a reported $24 million with the Blue Jays after posting a 4.35 ERA in 31 starts for the Reds and A's in 2019.

RHP Kevin Gausman: One year and a reported $9 million with the Giants after posting a 5.72 ERA in 102 1/3 innings for the Reds and Braves in '19.

RHP Michael Wacha: One year and a reported $3 million (plus $7 million in possible incentives) with the Mets after posting a 4.76 ERA in 126 2/3 innings and dealing with injuries with St. Louis in '19.

RHP Josh Lindblom: Three years and a reported $9.125 million (with a total possible value around $18 million with performance bonuses) with the Brewers after spending most of the past five seasons pitching in Korea.

Another free-agent starter who garnered lucrative deals so far this offseason was right-hander Zack Wheeler (five years, $118 million with the Phillies). Within the second-tier group of arms, righty Kyle Gibson (three years, $28 million with Texas), righty Michael Pineda (two years, $20 million with Minnesota) and lefty Cole Hamels (one year, $18 million with Atlanta) have also reeled in new contracts.

Lefties Madison Bumgarner, Hyun-Jin Ryu and Dallas Keuchel remain on the open market, with such pitchers as Rick Porcello, Wade Miley, Julio Teheran and Alex Wood a few pegs down the board. So far, even reclamation projects or pitchers who were non-tendered have commanded the type of cost that might make the Cubs a bit uncomfortable, given the extent of the team's needs.

If the Cubs can swing trades to address other needs, that could be an avenue to clear payroll space and more realistically look higher up the list of available free-agent arms.

The North Siders not only have a vacancy in the 2020 rotation, but they need to begin planning for the holes on the staff that will exist after the '20 and '21 campaigns. That is why the Cubs probably will target a younger, controllable arm or two as part of any trade discussions over Chicago's core stars (see: Kris Bryant and Willson Contreras).

"We have a couple starting pitchers under longer-term control," Epstein said. "And then we have a couple who are up after next year and not a lot of depth behind it, so it would be nice. But, you can't necessarily force it. We have a lot of needs, and, I think, if we were to move a really good player, you want to get talent back.

"It doesn't necessarily matter what position or what shape. But, yeah, it'd be certainly nice, over the course of this offseason, maybe next Trade Deadline, maybe next offseason, to make sure that we acquire impactful starting pitching at some point."

Chatwood and Jose Quintana, entering their age-30 and age-31 seasons, respectively, will be eligible for free agency next winter. Lester is 35 years old and has a $25 million mutual option ($10 million buyout) for '21. Darvish is 33 and signed through '23. Kyle Hendricks, 30, signed an extension last spring that keeps him locked in through '23 with an option for '24.

Behind that group, the Cubs have pitching prospects Adbert Alzolay and Alec Mills, plus Jharel Cotton and Colin Rea on the 40-man roster. While those four righties could contend for a spot on the pitching staff this spring, Chatwood would enter as the top fifth-starter candidate if there are no external additions. The Cubs would like to add more competition to the mix in the coming weeks.

"There's a lot of depth this year, a lot of volume," Epstein said. "Usually when that's the case, there's maybe some opportunity at the end [of the offseason]."