Keynan Middleton is entering a fourth straight offseason of MLB free agency, and while he wouldn’t mind finding his way back to the Yankees bullpen next year, he has his side hustle to keep him busy in the meantime: assistant varsity basketball coach at Rex Putnam High School in Milwaukie, Oregon.
The 30-year-old Middleton spends February through September of every year pitching, but feeds his other passion each winter by coaching high school basketball back home.
After spending the past nine offseasons as an assistant coach at his alma mater, Milwaukie High School, in a suburb of Portland — including three years as the head JV coach — he is joining their rivals this offseason at Rex Putnam, the former high school of Scott Brosius.
“I’m really excited about it,” Middleton said on the final weekend of the regular season. “That was something that when I was in the minor leagues and I didn’t even know I was going to be a big leaguer, ever, that was my fallback plan.
“I love basketball. I love being in the game. If I can’t play, coach. That was my way of staying connected to the game, but also in the offseason, it’s a way of passing time. My family loves it, too. My daughters come with me to practice, my wife used to play — we played basketball together at the same school in college. We’re a basketball family, we really enjoy it.”
Middleton went to Lane Community College in Oregon to play both baseball and basketball.
He jumped into his baseball season late as he finished out the basketball season, but a decision on his future was made for him once scouts saw him throw a bullpen session. The Angels drafted him with the 95th overall pick in 2013 and Middleton began his professional baseball career, which meant his days playing basketball were over.
But Middleton has been able to stick around the hardwood during the offseasons. He relished the chance to coach his brother the past few years at Milwaukie and now is set to coach his godmother’s son at Rex Putnam (Middleton said he talked with Brosius about the connection at Old-Timers’ Day last month).
“I’ll be getting right into it as soon as I get back home,” Middleton said.
“I was talking to somebody in the bullpen [recently], I don’t know how it got brought up, but I was like, ‘I don’t even think about baseball when I’m coaching.’ They’re like, ‘Not even during practice?’ I’m like, ‘No. I’m doing so many things, most of the time I’m half dripping in sweat because I’m working with the kids and stuff.’ I just really enjoy it.”
And yes, his high school players know what he does for a full-time job.
“When I was with Chicago [earlier this season], we played up in Seattle and one of the kids that’s going to be at the new school I’m coaching — I’ve never really met this kid, I’ve talked to him on social media — he came up to the bullpen and I sat there and talked to him the whole game,” Middleton said. “We just chopped it up the whole game.
“I think that’s the coolest part about it because when I was their age, I was kind of lost. I didn’t know how to work hard, what to do. If I had somebody like me in my shoes come back and share wisdom with me, like, ‘This is what it looks like. This is what hard work truly looks like.’ Nowadays, you can flex on Instagram with little posts or whatever. You can trick people into thinking you’re working hard. Being able to teach these kids what real hard work is, that’s the biggest thing for me.”
Middleton is hoping that his own hard work this year — which resulted in one of the best seasons of his career — will pay off with a major league contract this offseason.
In 51 total games with the White Sox and Yankees, he posted a 3.38 ERA across 50 ⅔ innings.
He was even better with the Yankees — despite coming in with an (unfairly to him) negative connotation because he was the Yankees’ only acquisition at an underwhelming trade deadline — recording a 1.88 ERA and 17 strikeouts during 12 games and 14 ⅓ innings. Two of the three runs he allowed as a Yankee came in his final appearance of the season, against the Royals, after spending three-plus weeks on the injured list due to shoulder inflammation.
Middleton was glad he got back before the season ended to prove he was healthy entering free agency again. A possible reunion with the Yankees could be in the cards.
“Honestly, there’s not too many other places I’m looking at,” Middleton said. “After being here, I don’t know why you wouldn’t want to be here. If it ends up working out, I’d love to come back here. But we’ll see what happens.”
It was only a two-month cameo in The Bronx, but Middleton seemed to genuinely enjoy it.
“I learned a lot and I loved it,” Middleton said. “Before I even got drafted, [Giancarlo] Stanton was one of my favorite baseball players; being able to play with him was cool. I didn’t know too much about [Aaron] Judge, but getting to know him, he became easily one of my favorite players. There’s other guys around here — Gerrit Cole, Clay Holmes, Michael King — it’s just pure greatness. Being around these guys and being able to learn from them has been huge for me.
“The coaching staff as well — the first day I got here, we tweaked some pitch grips, we went through some metrics I’ve never seen before and I feel like that gave me the confidence to just go out there and do my thing and not worry so much.”
Largely because of injuries, Middleton had to settle for signing minor league contracts in each of the past two seasons with the Diamondbacks and White Sox. He’s hoping he showed enough this year to earn a major league deal for next season.
Until then, though, Middleton can be found on the hardwood, dabbling in a part-time job he hopes to pursue further once his baseball career is over
“I hope by that time, I get enough experience — almost 10 years of experience as a varsity assistant, three years as a head JV coach,” Middleton said. “Hopefully I can get some type of head job when I’m done with baseball.”
AL East goes south
Purely by winning percentage (.554), the AL East was one of the best divisions in major league history this season. Since divisions came into play in 1969, only the 2002 AL West (.566) and 2001 AL West (.565) have had better collective records, according to the great Sarah Langs of MLB.com.
The gauntlet of a division passed the eye test, too, as the Yankees could attest with their 22-30 record against the AL East.
And then the division fell right on its face in the playoffs with the Orioles, Rays and Blue Jays combining for as many wins as the Yankees and Red Sox, who were watching from home.
Of course, that shouldn’t make the Yankees feel any better about their brutal season.
They still need to be using October to figure out a way to get better because the rest of the division isn’t going anywhere anytime soon — especially the Orioles, who have even more talent on the way and should be able to use getting swept by the Rangers in the ALDS as important experience moving forward (plus beefing up their pitching staff wouldn’t hurt).
It is strange, though, looking at the AL East’s performance in the postseason of late.
Between this year and last, AL East teams have combined to go 3-17, getting swept in six of seven series. The three wins were courtesy of the Yankees’ ALDS victory over the Guardians in five games last October.
Nestor on the mic
In case you missed it, Nestor Cortes will appear on an alternate telecast of the NLCS on TruTV and the Max app.
He will be joined by fellow current and former Hispanic or Latino players Pedro Martinez, Albert Pujols, Yonder Alonso and Kenley Jansen, breaking down the games while having conversations about Hispanic culture in baseball.
