The chaotic, historic, borderline-comedic year that made Oliver Drake MLB's most wanted unwanted man
In 2018, Drake endured a volatile season of short leashes, broken leases, and a relentless stretch best encapsulated by a 10-second exchange from a sitcom.
If you look up the definition of ‘designated for assignment’, it’s surprisingly easy to associate one specific player with the transaction.
Hundreds of players have passed through baseball’s procedural purgatory—DFA’d to make room, buy time, or reshuffle a roster. Some are struggling. Others are fading. A few are out of options. And some just haven’t tapped into their potential.
And then there’s Oliver Drake—who, in 2018, somehow managed to check all those boxes at once.
The Worcester, Massachusetts, native was DFA’d five times that season. He pitched for five different teams, setting a modern MLB record —and earning himself the nickname “All Over” Drake and the not-so-coveted honor of being the featured photo on Wikipedia’s DFA page.
There’s no actual footage of MLB front offices talking about Drake that year.
But if there were, this clip from the most popular sitcom in television history might come closest to capturing the energy:
For the uninitiated, ‘The Drake’ was a minor but memorable Seinfeld character — liked or loathed depending on the moment. Jerry and Elaine loved “The Drake” when he was engaged and gift-worthy. But once the engagement ended and their expensive present couldn’t be returned? “Hate the Drake!”
Their feelings weren’t really about the man himself. They were about what he represented in the moment: something to celebrate until it was time to cut ties.
Twenty-five years later, a fringe MLB relief pitcher with the same last name found himself moved around with impersonal frequency — teams claimed The Drake, then DFA’d The Drake.
In 2018, “The Drake” became baseball’s most wanted unwanted pitcher — enduring a volatile season of short leashes, broken leases, and a relentless stretch best encapsulated by a 10-second exchange from a sitcom.
“I don’t even like Drake!”
It’s not that teams didn’t like Oliver Drake. They just didn’t like him long enough.
It had nothing to do with his work ethic or potential — which he showed over a decade in the Baltimore Orioles’ system, where he climbed steadily despite long odds.
A 43rd-round pick in 2008 out of the United States Naval Academy, Drake found himself at a “crossroads” as he weighed a pro baseball career against serving his country.
"Oliver was at a crossroads in his life," Navy coach Paul Kostacopoulos told the Baltimore Examiner. "He took a huge leap in his progress the last 24 months, and he turned into a legitimate pro prospect. He just came to the realization that he could not pursue baseball any farther if he stayed at the Naval Academy."
After a “difficult decision,” Drake signed with Baltimore and his early minor league seasons were defined by grit. He was added to the Orioles’ 40-man roster ahead of the 2012 season, but just as he started dominating the professional ranks, a shoulder injury cut his year short.
“It was an exciting year and I was looking forward to it and I was actually pitching well at the time,” Drake reflected to MiLB.com about the 2012 season. “Then my shoulder started hurting. I got it checked out and unfortunately, needed surgery. Surgery is a scary thing; you don’t know how you’re going to bounce back.”
He did bounce back — big time. By 2015, he dominated Double-A, excelled at Triple-A, and earned a share of the Jim Palmer Minor League Pitcher of the Year award alongside Mychal Givens. That year, he debuted in the big leagues with three scoreless innings and a 2.87 ERA in 13 appearances.
He posted another solid minor league season in 2016 and appeared in 14 games for the Orioles.
However, after posting an 8.10 ERA in three appearances to begin 2017, the Orioles designated Drake for assignment.
Ten years. Drafted, developed, and rehabbed — only to exit not with a sendoff, but a note on the transaction wire.
He didn’t have to wait long for his next opportunity, however, as the Milwaukee Brewers pounced to acquire him in a trade hours after he was DFA’d.
“It’s exciting to get a new, fresh start,” Drake told MLB.com after the trade. “I only know one organization in professional baseball. It will be exciting to learn everybody’s name and the way things run.”
“You don’t like The Drake?”
One team’s DFA was another organization’s diamond in the rough.
Drake capitalized on his new chance: 61 games, 4.44 ERA, 59 strikeouts in 52.2 innings. He even notched his first save — and the Brewers even did their best Seinfeld impression.
Drake still had things to refine — mostly his mechanics and how he deployed his pitches. He wasn’t dominant, but he was dependable — and for a contending team that just missed the playoffs, that mattered.
If he kept it up, Orioles fans might’ve been inclined to echo Seinfeld: ‘You didn’t keep The Drake???”
“Hate the Drake!”
2018 began just like the year before — and not in a good way.
Drake was lit up to the tune of a 6.39 ERA in 11 games, quickly going from enticing to expendable.
The Brewers DFA’d Drake on May 1, kicking off a whirlwind rest of 2018 that would cement Drake as baseball’s ultimate nomad.
The Cleveland Indians were Drake’s first stop — ironically while the team was in Milwaukee, making his first commute a brief one — as the team sought to upgrade a dreadful bullpen. Cleveland sported a team ERA over 9 while dealing with an injured All-Star closer, Andrew Miller.
“Regardless of whether Drake can perform at a high level, it’s a low-risk move for a club in desperate need of some stability in its relief corps,” MLBTradeRumors wrote in its report, citing Drake’s career-high 10.66 K/9 rate with the Brewers as an encouraging sign despite his poor results.
He started strong — no runs in his first three outings. Behind the scenes, though, life was a scramble. He and his wife Shannon, temporarily assumed the lease of a fellow right-handed pitcher who had been DFA’d.
“So we go to Cleveland, the team is home for a couple days, then on the road for a two-week road trip,” Drake explained to CBS Sports. “We figure we don’t have to rush to find a place. Then we get lucky, we’re able to take over a lease from Matt Belisle, he’d moved on.”
The flicker of stability swiftly dissipated with one bad performance.
Drake had arguably the worst outing of his career, allowing five hits and six earned runs in just two-thirds of an inning on May 25 against the Houston Astros in an 11–2 loss.
That same day, they inked their lease and Drake’s wife began preparing their new apartment — all for naught.
“She had spent all day unpacking both of our cars and setting up the apartment,” Drake recalled on FanGraphs’ Effectively Wild podcast. “I remember calling her after the game and she was so excited about how she had the apartment all unpacked and set up and I had to tell her, ‘Well, we’re going to have to start packing that up again tomorrow morning.’”
“I love the Drake!”
Another team did, too — at least for the moment.
On May 31, the Los Angeles Angels of Anaheim claimed Drake off waivers, making them his third team of the season. By this point, even he understood what that probably meant.
“You’re trying not to live and die with every outing and wondering like, ‘Oh, if I have a bad one, am I going to be on the move again?’” Drake said.
Drake began his Angels tenure with two scoreless appearances. Then came two shaky outings — 1.1 innings, three earned runs — and with that, the cycle started again.
The Angels DFA’d him on June 16. This time, no one bit. No trade, no claim. Drake was outrighted to the Triple-A Salt Lake Bees, removed from the 40-man roster, and left waiting for someone else’s misfortune to open the door again.
To his credit, he earned it. Drake posted a 1.17 ERA in six games with the Bees, earning a brief recall a few weeks later.
Brief being the operative word.
After four appearances, the Angels DFA’d him again on July 23.
“I remember whenever it would happen, I would just fly back home which was different because I don’t think I’ve ever been home in the past 15–20 years during the summer because I was always playing baseball — whether it was college or in pro ball,” Drake said of his time in DFA limbo.
“So being home in June and July felt a little weird.”
“How could you not like the Drake?”
The Toronto Blue Jays were next up in Drake’s repeated game of roster roulette — making him the second most famous Drake in Canada.
He was claimed on waivers on July 26 and joined the team in Chicago, where the Blue Jays were set to begin a series against the White Sox.
However, logistical chaos reared its ugly head again.
“When I told [Shannon] we were headed to Toronto, she had this look like, ‘You gotta be kidding me,’” Drake said to The Gardner News. “She had just looked at her passport and realized it had expired like a week ago. So, she flew home and tried to expedite her passport.”
While his wife handled a passport snafu, Drake officially played for his fourth team of the season.
The results weren’t pretty: in his debut on July 27, he entered in the ninth inning of a game the Blue Jays led 10–2 and promptly surrendered three earned runs on four hits, before recording the final out. The following day, he entered in the ninth inning again, this time pitching a scoreless two-thirds of an inning in a 9–5 loss.
Given his cross-country tour, Drake had to be ready to pitch in a different city, for a different team — and soon, in a different country.
He revealed that during his various limbo periods, his only way of staying sharp was by throwing into a fence at his old Little League field.
“It feels like when you’re grounded and you’re watching all your friends play outside, and you can’t go play,” Drake said. “I’ll turn on games, and watch buddies, guys, now there are numerous teams I’ve played with, so I know a lot of guys. I just want to play, so those days you can’t do anything, it feels like you’re in timeout. Those are the worst.”
The Blue Jays DFA’d Drake on July 30 after the end of their White Sox series. He was back in limbo, but his wife no longer needed to expedite her passport.
“Who’s the Drake?”
Once again, Drake joined a new team when the Minnesota Twins claimed him on waivers on August 3. He was on the brink of setting a record by playing for his fifth team in a single season.
By this point, Drake and his wife had a rough draft to handle the whirlwind: forget leasing an apartment, stay in a hotel, and pack as lightly as possible.
“It’s not easy,” Drake said. “Fortunately, I have a great support system with my family and my wife. She’s probably been the savior of this whole thing because she’s been with me this whole year.
There’s been times she’s had to pack up apartments, line up car shipping, everything. We’ve just been bouncing all over the place. She’s really saved me a lot and made this a lot easier.”
Two months remained in the regular season — and no guarantee he’d even last the week.
But Twins President of Baseball Operations Derek Falvey saw something more than a traveling man with a high ERA.
“I think what each team has seen, and we’ve seen now, is a set of pitches with underlying metrics that indicate he can be a successful major league reliever, maybe more so than his surface-level stats,” Falvey told The New York Times.
In simpler terms: the numbers under the hood told a more promising story than Drake’s ERA.
Drake proved Falvey’s assessment correct as he settled in for his longest, most successful run of 2018.
In 19 games, Drake posted a 2.21 ERA and continued to strike out hitters at an above-average clip.
The season was over, but roster movement happens year-round. As the Twins made moves to upgrade the team, Drake could be one of the first casualties.
“WHO’S THE DRAKE?”
His strong finish notwithstanding, Drake found himself in the same relentless limbo during the offseason.
His transactions read more like a game of hot potato rather than two teams fighting it out for a desired player.
There was no question, he was in the vicious cycle of the 41st man: good enough to be the 40th man on a 40-man roster – until he was the 41st.
Back in the minor leagues, there was no clarity on what 2019 had in store — or if Drake would ever see the majors again.
“The Drake is good!”
The Rays kept Drake — and it paid off. The 2019 campaign became his breakout.
The well-traveled hurler appeared in 50 games for Tampa Bay, posting a solid 3.21 ERA across 50 appearances. He whiffed an eye-popping 70 batters in 56 innings and was a lethal weapon against left-handed batters, keeping them to an anemic .147/.163/.196 slash line.
Drake even found viral fame from pitches that seemingly defied physics.
“That’s kind of a pitch I use a lot and I usually get some pretty good results with it,” Drake told reporter Kenny Morales after the game. “I was just trying to get it down and away, and fortunately it ended up there and I got him to chase… I don’t really have any social media, but I got a lot of messages and texts from people who said they saw it on various platforms.”
He also recorded his first (and only) career base hit and run batted in on August 13, 2019, a rarity for a middle reliever even back when pitchers hit in the National League.
For one season, the Rays managed to unlock the potential that five other teams had shuffled Drake around the country trying to find.
Injuries and a COVID-19-shortened season limited Drake to just 11 disappointing appearances in 2020. An elbow injury in spring training of 2021 cost him the entire season and Drake never pitched in the majors again.
Drake never made an All-Star team. He never signed a long-term, lucrative contract. He also never failed to appreciate the opportunities he was given.
“I’m just grateful to be in the big leagues playing baseball,” Drake said to The Minnesota Score shortly after joining his fifth team of 2015. “That’s something I’ve told a bunch of people. I mean that’s not exactly a goal I set out to accomplish, but you know, I’m happy that five teams have given me a chance this year; it’s a something I’m very grateful for.”
Drake retired having worn seven different jerseys across six MLB seasons, pitched for five teams in his fourth year, notched three wins in 2017, enjoyed two above-average campaigns, and saw his Twins cap land in the Baseball Hall of Fame — a fitting tribute to one hell of a career.
"I do have jerseys from all of them,” Drake said. “So the man cave will have a lot of jerseys. It’ll be a heck of a story.”
Whether you love The Drake or hate The Drake, you have to respect The Drake.
SOURCES
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The adventures of Oliver Drake — MLB’s record-setting nomad who pitched for five different teams in 2018 — CBSSports.com. (2019b, January 15). CBSSports.com. https://www.cbssports.com/mlb/news/the-adventures-of-oliver-drake-mlbs-record-setting-nomad-who-pitched-for-five-different-teams-in-2018/
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Sanford, A. (2021, February 17). Tampa Bay Rays re-sign RHP Oliver Drake, trade RHP John Curtiss. DRaysBay. https://www.draysbay.com/2021/2/17/22280353/tampa-bay-rays-resign-oliver-drake
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