In January 2011, the Orioles signed Kevin Gregg to a two-year, $10 million deal with a team option for 2013. Gregg, signed by Andy MacPhail, was brought in to be the team's closer, primarily because he compiled 37 saves in 2010 after having somewhat of a rebound year with the Blue Jays.
Gregg has been a replacement-level reliever (-0.1 fWAR) throughout his career. In 2009, he posted a then-career worst fWAR of -0.3 after being traded to the Cubs and avoiding arbitration with a one-year, $4.2 million deal. The Blue Jays signed him for $2 million the next season, and he was decent but not great (0.8 fWAR). After receiving a $750,000 buyout because the Blue Jays declined his team options, Gregg was offered arbitration, declined, and became a free agent. Also, because Gregg was a Type B free agent, Toronto obtained a supplementary first-round pick in the 2011 draft. So that ended up being a shrewd signing.
Unfortunately, the same cannot be said for Baltimore's decision. The signing didn't make sense, not because Gregg was horrible, but because the Orioles inked him for multiple years and paid him too much money. As Daniel Moroz (linked above) pointed out at the time, the O's were essentially paying Gregg to be worth two wins above replacement in 2011 and 2012 combined. Instead, he ended his Orioles career with an fWAR of -0.5 and a rWAR of -0.4 when he was designated for assignment last September.
In his first season in Baltimore, Gregg struck out fewer batters and walked more of them than in 2010, while his HR/FB rate increased by about four percentage points -- a bad thing for any pitcher, but especially so for a flyball pitcher like Gregg. His velocity also dipped a bit, which was a trend that continued into 2012. His ERA jumped from 3.51 in 2010 to 4.37 in 2011.
With Dan Duquette in and MacPhail out, the Orioles did what they could to rid themselves of Gregg and his contract, offering to pay a chunk of his salary to ship him out of town. However, such a trade never materialized. But maybe fans were being too hard on Gregg, one Baltimore Sun columnist said. Maybe he would regain his Toronto-pitching form, "where he developed the reputation of a gamer who loved getting the ball in tight situations." That didn't happen. Gregg wasn't much better, posting a 4.95 ERA, though he did cut down on his walks. His HR/FB rate increased another three percentage points, but he was a little unlucky on batted balls (.338 BABIP).
Buck Showalter eventually learned how to use Gregg: let him mainly pitch in garbage time. In 2011, Gregg had seven blown saves in 29 total chances and pitched in many important/winnable games. In 2012, he had none because he didn't receive a single save opportunity. He also went from pitching in 59.2 innings in 2011 to just 43.2, his lowest total since his rookie year in 2003.
I doubt that's what MacPhail envisioned when he signed Gregg, but Showalter adjusted and figured out that he just wasn't that good. Maybe that's why average relievers shouldn't receive two-year, eight-figure contracts.
Still, I guess we should thank Gregg for sort of contributing to the Orioles' return to the playoffs last season. But mostly, we appreciate his exciting interaction with David Ortiz in July of 2011. Plus, we'll always remember the glasses.