5 worst free agent signings in Orioles history

For large-market teams like the New York Yankees or Boston Red Sox, free agency carries little risk. If the Yankees or Red Sox sign a player to a lucrative, long-term deal and the player fails to live up to expectations, the large-market team can bench or cut the player (still owing their full salary) and move on to the next big move. New York's signing of Jacoby Ellsbury and Boston's signing of Pablo Sandoval are just two such examples.

Small to mid-market teams, such as the Baltimore Orioles, are more risk-averse, and for good reason. One bad contract can hamper a team's ability to spend for several years. While this might not seem fair, the issue of a baseball salary cap and creating an equal playing field is an article for another day.

For the Orioles, handing Chris Davis a seven-year, $161 million contract in 2016 was not only a bad baseball decision (Davis was one of the worst players in baseball during the final years of the contract), but it continues to haunt the Orioles, who are paying Davis over $1 million annually through 2037.

We wrote about the worst contracts the Orioles ever gave out in 2023, and Davis, unsurprisingly, tops the list. This article narrows the scope and will examine the worst free agent signings in Orioles history.

5. Charlie Morton - 1 year, $15 million

Recency bias may be at play here, but Charlie Morton's rough start in Baltimore makes the list. The Orioles signed the veteran right-handed starter last winter, hoping that the 41-year-old would help offset the loss of ace Corbin Burnes, who bolted Baltimore for Arizona this past December.

Unfortunately, the Orioles' hopes for Morton have morphed into a nightmare scenario, where Morton has ping-ponged between the rotation and bullpen due to shocking ineffectiveness. In 10 appearances, Morton is 0-7 with an 8.82 ERA. Talk of "small sample sizes" and "he'll figure it out" is decreasing as the season goes on.

With that said, the fact that the Orioles are only tied to Morton for one season softens the blow and lands him at fifth on the list.

4. Danys Baez - 3 years, $19 million

In 2006, the Orioles endured their ninth consecutive losing season. Instead of addressing obvious issues with the offense and starting pitching that offseason, the Orioles oddly invested over $40 million in relief pitching. To no one's surprise, Baltimore failed to produce a playoff team in 2007 or shortly thereafter.

The Orioles' bullpen shopping spree saw them add lefty Jamie Walker (three years, $12 million), submariner Chad Bradford (three years, $10.5 million), and former closer Scott Williamson (one year, $900,000). But the biggest (and most expensive) headscratcher was the addition of Danys Baez on a three-year, $19 million deal.

Baez's first season in Baltimore could not have gone much worse. In 53 games, Baez went 0-6 with a 6.44 earned run average and was worth -0.6 wins above replacement. Baez missed the entire 2008 season due to injury before returning in 2009 for a somewhat more respectable 4-6 record and 4.02 ERA. To this day, it is unclear why the Orioles brass felt that spending over $40 million on relievers - and $19 million on Baez - would break their losing ways.

3. Alex Cobb - 4 years, $57 million

To be fair to the Orioles, signing Alex Cobb made sense. Baltimore was nearing the end of their competitive window with Manny Machado, JJ Hardy, Adam Jones, and Zack Britton approaching free agency. Cobb had pitched well for the Tampa Bay Rays, and the Orioles signed him and Andrew Cashner prior to the start of the 2018 season to stabilize the rotation. Unfortunately, Cobb struggled with effectiveness and injuries, going 7-22 in 41 games before being traded to the Los Angeles Angels ahead of the 2021 season.

2. Ubaldo Jimenez - 4 years, $50 million

The Orioles struck late in the 2014 offseason, signing Ubaldo Jimenez to anchor their rotation and slugger Nelson Cruz to add veteran power to the lineup. While Cruz put up terrific numbers in his lone season in orange and black, Jimenez labored through four years in Baltimore, seesawing between the rotation and bullpen.

While adding a potential top-flight starter made sense at the time of the deal, Jimenez was a high-risk, high-reward signing, as issues with command plagued him during his career. Ultimately, Jimenez is best known for one of the darkest moments in Orioles history: allowing a walk-off three-run homer to Edwin Encarnacion in the 2016 Wild Card game.

1. Albert Belle - 5 years, $65 million

Like the Cobb signing, the decision to sign Albert Belle was not a bad one in a vacuum. The Orioles added Belle to replace the offensive production of the departing Rafael Palmeiro and Roberto Alomar after the 1998 season. The mercurial Belle was solid in his first two seasons in Baltimore, before a degenerative hip condition forced him to retire after the 2000 season, with some $49 million remaining on his deal.

For a mid-market team like the Orioles, having Belle clog up so much payroll was a recipe for disaster. Baltimore did not land another big free agent until Miguel Tejada in 2004.