The 2022 winter meetings convene next Sunday in San Diego, where eight years ago the Chicago Cubs signed Jon Lester in what is considered the most important free-agent signing in franchise history.
Not to put any pressure on team President Jed Hoyer — who was then serving as general manager and best supporting actor to Theo Epstein — but it’s time to put his own stamp on a winter meeting.
An “intelligent” spending spree may be Hoyer’s preferred course of action over a big-ticket item, but we’ll have to wait to see. The teams, media members, agents, honchos and wannabe honchos begin congregating Dec. 4 at a downtown Hyatt Hotel, with the meetings starting the next day and running through Dec. 8.
By that point we should have a good idea of where Hoyer is headed, even if nothing is announced.
The winter meetings are something of an anachronism in the smartphone era. Last year teams spent about $1.7 billion on free agents before the Dec. 1 lockout by owners, knowing signings would be prohibited for at least a couple of months. The pre-deadline movement suggested big deals can get done without clandestine meetings in hotel suites stocked with liquor and salty snacks.
We were robbed of a true Hot Stove League last winter. The winter meetings were held last December in Orlando, Fla., but MLB bowed out and left it for the minor leagues. This could be a return to an old-fashioned, pre-pandemic doozy of a winter meeting. Teams have thus far declined to jump cannonball-style into the free-agent waters, potentially saving their heavy lifting for San Diego.
Modern executives don’t even try to live up to the old standard set by late GM Kevin Towers, who didn’t mind conducting business at the hotel bar with a glass of whiskey, a cocktail napkin and a handshake.
It was a different time. Former Cubs GM Jim Hendry once signed pitcher Ted Lilly to a four-year, $40 million deal during the 2006 meetings in Orlando after being taken to a hospital with chest pains.
“Jim was hooked up to an EKG machine, and we got it done,” Lilly’s agent, Larry O’Brien, announced that day.
The Cubs spent nearly $300 million that winter, nearly doubling the next highest-spending team, the Boston Red Sox, then run by Epstein. Now you can offer $300 million to one free agent and still come up short.
Cubs Chairman Tom Ricketts is at a crossroads two years into the post-Theo era. He lauded Hoyer’s not-to-be-named game plan in September, calling it a big “success” in the first year and a half after the sell-off and promising to open up the digital checkbook.
“He’s got a lot of flexibility, and we’ll let him do it,” Ricketts said of Hoyer. “I have confidence Jed knows what he’s doing.”
Hoyer, in turn, has conveyed a sense of urgency. Cubs fans have begun showing signs of impatience — mostly by not attending games or watching them on Marquee Sports Network — and questioning whether all the revenue-enhancing additions to Wrigley Field are really going back into the team.
It was one year ago that Hoyer signed pitcher Marcus Stroman to a three-year, $71 million deal on the eve of the lockout, desperate to get one familiar name before the game shut down for the next few months. Stroman, who went 6-7 with a respectable 3.50 ERA in 25 starts, has an opt-out after this season and no doubt will be seeking a longer deal with the Cubs or elsewhere.
Like most teams, the Cubs have been doing their due diligence and waiting for the dominoes to start falling. They’ve hired a virtual college of hitting coaches — four at last count — and need to add a few more quality hitters to actually coach. Nico Hoerner, Ian Happ and Seiya Suzuki are the only returning regulars who hit higher than .250. There are openings at almost every other spot.
While the Cubs appear to be all-in on signing one of the Big Four free-agent shortstops, Hoyer also points out they are happy with Hoerner, who showed enough progress in ‘22 to deserve a starting position. The question is exactly where he’ll start.
If they don’t sign one of the four — Trea Turner, Carlos Correa, Xander Bogaerts or Dansby Swanson — they’d be satisfied with Hoerner at short and would move to other areas of concern. But as motivated buyers, and with all the talk about having flexibility, it would be prudent for Ricketts to back up the bold talk. The Cubs officially swallowed the final $22 million of Jason Heyward’s deal, a good sign they’re serious.
Before the Cubs signed Lester in 2014, Epstein spoke of the precarious “balancing act” between overpaying for a free agent too soon in the rebuild and remaining patient.
“If you’re counting on one free agent who by definition you’ve paid more for than ... anyone else in the industry, you’re usually buying some phase of his decline,” he said. “If you’re counting on that player to make the difference for you and he must perform, I think you’re on a bit of a fool’s errand.”
Epstein promptly signed Lester to a six-year, $155 million deal, signaling the start of the pivot toward contending. Misdirection was one of his go-to moves.
I can recall leaving the winter meetings hotel in San Diego to get some fresh air, only to spot Epstein and Hoyer huddling outside a nearby hotel, literally in the shadows, like a couple of spies. They seemed to love the skullduggery of a top free-agent pursuit.
I waved and went back to the MLB hotel. A couple hours later, the Lester deal was confirmed and the hotel lobby was buzzing.
“People ask if we’re all-in for 2015,” Epstein said the next day. “The best response is we’re all-in for the future. The future starts in ’15. We’re going to do some things to put as competitive a roster as possible on the field to try to win. Our goal is to win the division and then, as Joe (Maddon) said, the World Series.”
Seemed like a good idea, and it turned out to be the right one.
Can Hoyer turn back the clock to 2014 and re-create the magic of that memorable week, with his hands on the wheel this time and GM Carter Hawkins as his Dr. Watson?
It’s elementary.
