(2) Albert Belle, 5 years, $65M
I was in fifth grade when I came across the headline from the Baltimore Sun: the Orioles had lost Rafael Palmeiro to Texas, but signed slugger Albert Belle away from Chicago. I was thrilled! Albert Belle, with the mean-looking, intense stare and serious-looking stance was coming to Baltimore. He was coming off a tremendous season with the White Sox, having hit .328 with 49 home runs, 152 RBIs, and a 1.054 OPS.
Belle was solid in his first two years with the O's, posting OPSes of .941 and .816, respectively while primarily playing in right field. A degenerative hip condition would sideline Belle for the remaining three years of the contract and effectively ended his career.
(1) Chris Davis: 7 years, $161M
It is impossible to sugarcoat this one. This contract stunk. Following a strong 4.5 seasons with the team, the Orioles seemingly outbid themselves by signing Chris Davis to a whopping 7 year, $161M contract. There were reports that the Orioles were moving in a different direction due to Davis and his agent Scott Boras' ridiculously high demands, the Orioles' acquisition of Mark Trumbo to play first base, and the availability of other free agent bats such as Justin Upon and Yoenis Cespedes. Rumors began to swirl that Peter Angelos wanted to keep Davis, a fan favorite for his prodigious power, for the foreseeable future. This led to the largest contract ever given out in Orioles' history.
Many fans and reporters, myself included, hated the deal before the ink dried. When Davis was hot, he was one of the best hitters in the league. But when he was struggling - and he had his struggles - it looked like he was swinging the bat with his eyes closed. Many fans, myself included, feared that the latter Davis would begin to show up with more frequency.
Prophetically, with the contract signed, Davis began one of the most devastating declines in Major League history. In 2016, he registered a passable OPS of .792. However, considering the huge contract he signed, this was a big disappointment. It was all downhill from there. Davis was worth an incredible -4.9 WAR over the final four seasons of his career before he mercifully retired before the 2021 season.
Again, there is nothing to sugar coat here. Davis was awful from 2017-2020. Absurd contract aside, he was literally one of the worst regulars in the entire Major Leagues. This contract haunted the Orioles for years and perhaps represents one of the many reasons they now get stage fright when it comes to signing free agents.
But let me reiterate that signing free agents does not need to be a bad thing! One player I lobbied for the Orioles to sign last offseason, Nathan Eovaldi, just helped pitch the Texas Rangers to the World Series in the first year of a 2 year, $34M contract. This was a contract the Orioles should have absolutely matched, or even beaten, but opted not to.
This offseason, there will be several interesting free agents who the Orioles should explore signing: Aaron Nola, Blake Snell, Cody Bellinger, and Eduardo Rodriguez. Let's hope the Orioles can remain diligent, while also not allowing the sting of poor contracts past hold them hostage.