The Winter Meetings are approaching, and the Orioles’ pursuit of top-tier free agents could be heating up.
According to Jon Heyman of The New York Post, the Orioles have interest in Houston Astros star left-hander Framber Valdez and have “checked in” on Japanese star Tatsuya Imai. They also have shown interest in Philadelphia Phillies slugger Kyle Schwarber and approached Dylan Cease before he came to an agreement with the Toronto Blue Jays this week.
In December 2024, the Orioles came to agreements with outfielder Tyler O’Neill and catcher Gary Sánchez the night before the Winter Meetings began.
The Orioles might sign a free-agent pitcher to numbers uncharacteristic for them, but the seven-year, $210 million price tag for Cease, who was only 8-12 with a 4.55 ERA in 32 starts, seems steep. He also had a relatively low 1.1 WAR (Wins Above Replacement).
Now that Cease, who MLBTradeRumors.com ranked as the third most attractive free agent and predicted would get a seven-year, $189 million, is accounted for, Valdez is the next pitcher on their list. They think he could receive a five-year, $150 million deal
Signing him would be a coup. He had a 13-11 record with a 3.86 ERA in 31 starts for the Astros, and his WAR was 3.8.
Valdez threw 192 innings in 2025. Dean Kremer led the Orioles with 171 2/3 innings. That would be attractive to the Orioles.
Behind Valdez, ranked sixth by MLBTR, is Imai, predicted to be signed to a six-year, $150 million deal.
President of baseball operations Mike Elias signed his first Japanese import a year ago, 35-year-old Tomoyuki Sugano. He was second to Kremer with 157 innings, and is a free agent after playing out a one-year, $13 million contract.
Imai, who’s 27, was 10-5 with a 1.92 ERA in 24 starts with Japan’s Seibu Lions in 2025. He was a teammate of Orioles reliever Dietrich Enns in 2022 and 2023.
In 2025, Imai threw five complete games, three shutouts, and allowed just 5.6 hits per nine innings. Imai allowed just six home runs in 163 2/3 innings.
In one sense, Imai would be more attractive to the Orioles than Valdez because they wouldn’t have to surrender a draft choice to sign him. But I don’t think the draft choice issue will be a deal-breaker for the Orioles this offseason.
While the signing of Valdez or Imai would be welcome, it wouldn’t be shocking.
Seeing the Orioles outbid the Phillies for Schwarber would be astounding.
New lead hitting coach Dustin Lind has worked with Schwarber with the Phillies, and that could help Schwarber feel comfortable.
Schwarber would feel at home in Baltimore with its close right-field home run distances.
In the National League for most of his career, Schwarber has hit three home runs in his eight games at Oriole Park. In 2025, he hit 56 home runs and drove in 132 runs. Though he struck out 197 times, he walked 108. While he hit only .240, Schwarber had a .365 on-base percentage.
His signing here, while unlikely, might excite the fan base even more than a top starter.
Shildt’s addition an intriguing one
The Orioles haven’t announced the reported addition of former St. Louis Cardinals and San Diego Padres manager Mike Shildt as upper level field coordinator, but his experience could help the team.
Shildt has a lifetime winning percentage of .561, fourth highest of any 2025 manage behind only Dave Roberts (Dodgers), Aaron Boone (Yankees) and Rob Thomson (Phillies).
In each of Shildt’s six full seasons of managing, his teams qualified for the postseason yet last month he abruptly retired from the Padres.
Shildt and Elias worked together in St. Louis in the past. He was fired in St. Louis after the 2021 season, a year where the Cardinals won 17 straight late in the season before losing a Wild-Card game to the Dodgers.
His youthful ties to the Orioles are well-documented. Shildt’s mother worked for the Orioles’ Double-A Charlotte team and he was a bat boy for the team and a huge admirer of Cal Ripken Jr.
Call for questions: I answer Orioles questions most weekdays. Please send yours to: Rich@BaltimoreBaseball.com.