Revisiting past Winter Meetings for Orioles

What can be expected of the Orioles this week?

Maybe the unexpected, like when they didn’t select a player in last year’s Rule 5 draft and made a huge splash by signing closer Craig Kimbrel to a $13 million contract for the 2024 season.

With the 24^th pick in this year’s Rule 5, the Orioles most likely will pass again rather than try to carry a player for the entire season while also attempting to make a deep playoff run. Executive vice president/general manager Mike Elias dropped some strong hints at last year’s Winter Meetings that the club wouldn’t participate in the major league phase unless players on their board surprisingly fell to them. He could do the same with media covering this year’s event, which is arguably the second-biggest for fans after spring training, and gathering daily in his suite.

Kimbrel’s signing ranks as one of the biggest stories in Orioles’ Winter Meetings history. His contract was the largest handed out in Nashville, much to the amusement of some club officials who didn’t realize it until later. They outspent the Dodgers and Yankees, who, of course, sped past them later.  

At least one minor league signing is typical, especially on the first day. Infielder John Lester and outfielder Nomar Mazara joined the organization as free agents on Dec. 6, 2022. The pandemic caused the cancellation of the 2020 in-person meetings, which were held virtually and included the Orioles claiming right-hander Ashton Goudeau on waivers from the Pirates.

They claimed right-hander Marcos Diplan on waivers from the Tigers in 2019, continuing a trend of moves that didn’t improve the club but provided some depth in the system.

One of the most impactful, at least for a brief time, was the 2018 waiver claim of infielder Rio Ruiz from the Braves. Elias drafted Ruiz in the fourth round in 2012 when he was the Astros’ special assistant and scouting director. The 2018 offseason was his first with the Orioles.

Elias also is known to swing a trade or sign a major league free agent leading up to the meetings. It happened again Saturday when the Orioles reached agreement with outfielder Tyler O'Neill on a three-year, $49.5 million contract and catcher Gary Sánchez for $8.5 million next season.

Elias had an agreement with Kyle Gibson shortly before the 2023 meetings, dealt Dylan Bundy to the Angels on Dec. 4, 2019 for a four-player minor league package that included Kyle Bradish, and traded Jose Iglesias to the Angels on Dec. 2, 2020 for pitchers Jean Pinto and Garrett Stallings.

The Orioles were in the thick of their rebuild.

The previous regime, led by Dan Duquette, traded catcher Steve Clevinger to the Mariners on Dec. 2, 2015 for first baseman Mark Trumbo and left-hander C.J. Riefenhauser. Trumbo hit 47 home runs in 2016, was an All-Star and won his only Silver Slugger. The Orioles got the better of that deal.

Going back to Winter Meetings trades, the Orioles acquired left-hander Dana Eveland from the Dodgers for two minor leaguers on the day of the 2011 Rule 5 draft. It added some unexpected weight to the media’s workload. But it’s hard to top the 2010 event in Orlando, when the Orioles traded for third baseman Mark Reynolds and shortstop J.J. Hardy.

Reynolds came from the Diamondbacks, who received pitchers David Hernandez and Kam Mickolio – the latter being part of the Erik Bedard trade with the Mariners that brought Adam Jones to Baltimore. Hardy and infielder Brendan Harris came from the Twins for pitchers Jim Hoey and Brett Jacobson. The streak of non-winning seasons was nearing an end.

I’ve chatted with Hoey at a few Winter Meetings and suggested that he come back to Camden Yards for autograph signings. He joked that fans wouldn’t want to see him, but I pointed out that he’s loved because he helped to bring Hardy to Baltimore.

What I remember about the Hardy deal, beyond the conference call with media huddled around the phone, was the Orioles' simultaneous negotiations with the Rays for shortstop Jason Bartlett. Which team would bite first?

Brady Anderson didn’t want the club to trade Nolan Reimold to the Rays. They worked out together in the offseason and Anderson thought Reimold was primed for a big year. I kept writing that Bartlett was the better defender because I had it in my head that Hardy was a bat-first guy. Hardy won three consecutive Gold Gloves, was one of the best “taggers” covering second base – which manager Buck Showalter loved to point out – and posted a career 17.5 dWAR. Barlett never won a Gold Glove and had a 7.3 dWAR.

So much for my career in scouting.

Hardy was the captain of the infield and a huge reason why the Orioles made the playoffs three times in six years. The recurring back injuries were unfortunate, to say the least.

If we're talking big-time signings, we can't forget Miguel Tejada agreeing to a six-year, $72 million deal in New Orleans in 2003, the longest and largest free-agent contract in franchise history at the time. I can still see the smiles on the faces of executives Jim Beattie and Mike Flanagan as they walked out of an elevator.

"How many chances do you get to add an MVP-caliber player to your club who wants to be there for a long time?" said new Orioles manager Lee Mazzilli.

The Orioles acquired starter Kevin Millwood from the Rangers for reliever Chris Ray at the 2009 meetings in snowy Indianapolis. Rumors of their interest in Millwood swirled for days, leading to at least one false report about the Orioles sending Felix Pie to Texas.

An MLB.com article posted about a week before the meetings claimed that the Rangers weren’t interested in moving Millwood. Until they did.

"I'm a little surprised,” Millwood said after the trade. “It feels weird, but what can you do? I liked it here in Texas. I've had a great time and enjoyed playing with great teammates. I was hoping to finish here, but that's not going to happen."

OK, so he wasn’t immediately jazzed about pitching for the Orioles.

Catcher Ramón Hernández was dealt to the Reds at the 2008 meetings in Las Vegas for Justin Turner, Ryan Freel and Brandon Waring. The Orioles would have been wise to hold onto Turner instead of exposing him to waivers in May 2010. The Mets claimed him.

The meetings also can be memorable for what doesn’t happen.

The Manny Machado trade rumors in December 2017 in Lake Buena Vista, Fla. netted nothing, but my legs ached from chasing them. He stayed with the Orioles until the start of the teardown in July 2018.

News broke in Florida that the Orioles were willing to listen to offers, that Machado was on the table, but I never bought that they were actively shopping him. I had it confirmed that they talked to the Dodgers, Cardinals and Phillies, and the White Sox and Giants also made offers.

In an attempt to bond with Jack Flaherty last year, I approached his locker, introduced myself and mentioned how I wrote about him multiple times because he was one of the prospects that the Orioles wanted in exchange for Machado, along with catcher Carson Kelly. Flaherty, with his back turned to me, replied, “That was a long time ago.”

Yes. Yes it was.

We’ll find out this week whether the Orioles find their starting pitcher and reliever, or if the groundwork is laid for future moves. Maybe they'll sign Flaherty.