Keala Montgomery was born and raised on Lanai.

The remarkable legacy she leaves there — on and off of athletic venues — as she embarks on a college adventure that is set to include a softball career will be remembered and felt for a long time to come.

A quick look at her accomplishments in athletics as a Lanai High School senior shines brightly.

In the fall, she changed positions — from middle blocker to outside hitter — and still was a key part of the Pine Lasses’ run to a New City Nissan/HHSAA girls volleyball state tournament berth for the first time since 1999 when they won the then-single level Maui Interscholastic League title.

She earned the first of her three MIL Division II first-team All-Star recognitions for the 2022-23 school year in volleyball.

In the winter, she was one of four first-team MIL All-Stars for the first Lanai High basketball team, boys or girls, to win an MIL title.

In the spring, she was the pitcher, Player of the Year for the second straight year and only senior on the Pine Lasses’ softball team that rallied from an 0-2 start to win the MIL crown.

Outside of athletics, she was perhaps even more impressive, earning “seven or eight” scholarships that will total about $15,000 per year as she attends Kenyon College, an NCAA Division III school in Gambier, Ohio, where she was awarded another $59,000 per year in merit scholarship money.

She was the first Lanai girl ever selected to the HHSAA Hall of Honor and followed up being junior class president with being Lanai High’s student body president this year.

Today, Montgomery adds another unprecedented honor — she is The Maui News MIL Girl Athlete of the Year, the first from her tiny school.

“It’s pretty crazy, it’s definitely something that I always looked at, like, ‘Oh, wow, like this girl is athlete of the year, it’s amazing,’ and now I’m her and it’s just a pretty incredible feeling,” Montgomery said via phone from California on Tuesday.

Naighel Calderon, currently a member of the University of Hawaii baseball team, was the first from Lanai to win the MIL Boy Athlete of the Year award in 2018-19. The awards date back to 1991.

“I know him somewhat, I’ve talked to him before,” Montgomery said. “It means so much and I mean when Naighel got it that was definitely like, an ‘Oh, wow, this kid from Lanai got this, such a high honor.’ That was motivation for me to think: ‘Oh hey, this is something I can do.’

“And now that I have it I definitely want this to be something that other younger kids can use and be like, ‘Hey, she got it.’ With a school that has a K-through-12 school, super small, one island, I really hope that other kids think the same thing that I did when I looked at Naighel.”

Listening to her high school head coaches shows just how special Montgomery is to her island and her school. Her parents Jon and Jennifer Montgomery are both teachers at Lanai High and Elementary School.

“Oh my gosh, Keala, where do you begin? Just with her in general, she comes from a family that they are very disciplined, very hard-working — she brings that to every single sport that she’s in,” Lanai girls basketball coach Christian Yumol said Wednesday. “Basketball is no different. We know her also as the stud softball player — that’s what she is — but in terms of basketball I could always rely on her work ethic. Her work ethic was second to none.”

Twice in her basketball career, Montgomery grabbed 17 rebounds at state tournament games — against Sacred Hearts in 2023 and in 2020 as a freshman against Campbell.

Yumol said there is no doubt that Montgomery left a lasting legacy in Lanai City.

“She absolutely did and everything that she brought to us she brought to all of our programs,” Yumol said. “It was not just on the field or on the court, but it was in the classroom, it was in the community. She was very heavily involved. Again, I talk about her parents, she comes from a really, really, really good upbringing, they’re both teachers.

“She’s a special kid and everything that she’s been able to achieve in her high school career has been amazing.”

Yumol knows Calderon well, too, and he said there is something perhaps a little bit more to Montgomery’s legacy.

“Both of them, you mentioned Naighel and now with Keala, and you know, they’re the first and we said it with Naighel before that we’re not sure whether we’re going to see another one come through like that,” Yumol said. “And we ended up seeing Keala come through and she honestly, probably, she probably did more than he did.”

Volleyball coach Ross Morita was similarly impressed. He took some advice from veteran Molokai volleyball coach Hale Domingo on what to do with Montgomery.

“He always said, ‘Outside hitter, that’s your money, that’s the ones who are going to score all the points,’ ” Morita said. “Years prior, because she was tall, we used her at middle blocker, but then I kind of had to get away from that and I looked at her and said, before the season started, I said, ‘Hey Keala, I’m going to challenge you this season. You’re going to play all-around, I’m going to put you as an outside hitter. I know it’s your senior year, you’ve never played this position before, but we’re going to play really, really fast this year.’

“And then what happened, she had never passed any balls before, like serve receive, and then she killed it with serve receive. … She was excellent as an outside hitter. I kind of wish I’d changed her position even in her junior year.”

Softball coach Robbie Sanches was watching the whole way as Montgomery was excelling at other sports.

Three Lanai softball starters missed the first four games of the season due to discipline and with no other seniors on the roster, it was up to Montgomery to lead the way.

“She’s kind of a silent leader, she won’t say much, but I guess she’ll do it in her actions, she did good,” Sanches said. “I think this is a once-in-a-lifetime athlete for here. I mean, you don’t always see that.

“I always preach that if you are going to be one all-around athlete you’re really not going to be good at all of them. You have got to commit to one that you like and work on that to be great, but her, I don’t know. She had the bloodlines, she was good in all.”

Sanches shook his head at how effective she was in every sport.

“I just was worried that ‘don’t get hurt, don’t get hurt, because then our season’s over,’ ” he said. “She did good.”

Montgomery will miss both volleyball and basketball. Fellow senior standouts Souina Seiuli and Haley Ostrander were both All-Stars in each sport, Ostrander being MIL Player of the Year in basketball.

“Haley and Souina, we all played volleyball, basketball together and it’s just super fun,” Montgomery said. “In volleyball, most of us didn’t even realize when we started the season off and then once we started playing our games, started winning more, we were doing pretty good and then coach Ross told us how long it’s been (since making a state tournament) and we started thinking, ‘Oh my gosh, that’s so crazy.’

“Then we went to the state tournament and it was so exciting. Another little piece of history that I got to be a part of, which was so cool. … I played with Haley and Souina, it feels like forever. I’m going to miss that connection we had off and on the court.”

That volleyball run and the momentum that came with it carried into basketball season.

“Oh a bunch, volleyball, that state run wasn’t expected, but then we went into the season for volleyball just wanting to have fun, get better, win when we could, but we weren’t expecting everything that we did,” Montgomery said. “So, that definitely gave us the confidence going into basketball. Like, ‘Hey, if we can do it for volleyball we can do it for basketball; basketball, we got this’ — that’s the mentality we went into basketball with and volleyball helped a bunch.”

The Montgomery train rolled into Olinda with her basketball team in tow for the MIL tournament, and the Pine Lasses cut down the nets at the Erdman Athletic Center when the clock hit zero.

“It was so cool and the support that we had, all of the Lanai people there, all of the friends and family that came to support us, was just amazing,” Montgomery said. “I’m pretty sure the MILs for this past year were supposed to be back home on Lanai and so at first we were super disappointed. We were like, ‘Oh my gosh, we won’t have the chance to win it this year, it’s not going to be at home,’ but then all these people came and showed up to support us and that was just amazing. Definitely one of the highlights of my sports career.”

The team, coaches, friends and family filled Zippy’s in Kahului for the post-championship meals.

“That was fun, that was sort of our sit there and eat and let it all soak in and, ‘Wow, at last we’re the champions and after all this hard work we finally did it,’ ” Montgomery said.

She will miss basketball a lot as well.

“I think the bond that we had as a team, I think especially basketball, with the coaches and the girls, we went through so many losses to that point and we went through it all together,” Montgomery said. “Everybody sort of stuck through, so yeah, I’m going to miss it a lot. It was a really, really good team that turned into family with the coaches and the girls.”

Montgomery vividly remembers sitting in the school’s tiny gymnasium and softball/baseball fields and watching the Pine Lads and Lasses play.

She was a standout baseball player until the Pono Foundation started a softball program on the island when she was 10, and now she is one of the Pine Lasses that the young Lanaians will remember.

Before leaving on a family vacation recently, Montgomery was part of a group of recent graduates who were helping out at middle school girls basketball practices.

“Oh, I take a bunch of pride because I can remember being young and in middle school and elementary and watching those, you know, the high schoolers play — we’d always go to the games as a middle school team,” she said. “The coaches would point things out to us, ‘Oh, watch her, watch her,’ and so that was always kind of going through my head when we would play. These younger kids who were just like me and looking up to us, I take huge, huge pride in that.”

* Robert Collias is at rcollias@mauinews.com.

MIL GIRL ATHLETES OF THE YEAR

1990-91–Kimmie Ouchi, Seabury Hall

1991-92–Jean Okada, Lahainaluna

1992-93–Joelynn Naki, Baldwin

1993-94–Kari Luna, Baldwin

1994-95–Prestine Foster, Baldwin

1995-96–Aina Kohler, Lahainaluna

1996-97–Aina Kohler, Lahainaluna

1997-98–Aloha Santiago, Baldwin, and Lisa Arcangel, Lahainaluna

1998-99–Cassie Coffin, St. Anthony

2000-01–Nicole Garbin, Baldwin

2001-02–Ashlyn Russell, Baldwin

2002-03–Chandi Bickford, King Kekaulike

2003-04–Kami Kapaku, Baldwin, and Tia Ferguson, Seabury Hall

2004-05–Emalia Suehiro, King Kekaulike

2005-06–Tiara Dole, St. Anthony

2006-07–Chelsea Machida, Maui High

2007-08–Bailey Massenburg, King Ke­kaulike

2008-09–Bailey Massenburg, King Ke­kaulike

2009-10–Kalei Adolpho, Molokai

2010-11–Kalei Adolpho, Molokai

2011-12–Dakota Grossman, Seabury Hall

2012-13–Dakota Grossman, Seabury Hall

2013-14–Dakota Grossman, Seabury Hall

2014-15–Lalelei Mataafa, Lahainaluna

2015-16–Lalelei Mataafa, Lahainaluna

2016-17–Ava Shipman, Seabury Hall

2017-18–Veronica Winham, Seabury Hall, and Rebecca Buenrostro-Gallimore, Baldwin

2018-19–Chloe Gangnath, Seabury Hall

2019-20–Nanea Estrella, Lahainaluna

2021-22–Kaylee Volner, Seabury Hall

2022-23–Keala Montgomery, Lanai

Note: No winners selected in 1999-2000, 2020-21