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He began life as a professional cricketer batting right at the top of the order but, by his own admission, he wasn't doing enough to dislodge the openers New Zealand already had. Very few could match up to what Martin Guptill provided at the time, which is why in 340 of the 367 times he put on the Black Cap, he was also out there dealing with the first ball.
"I wasn't playing nearly consistently enough to push somebody out of their position," Phillips told ESPNcricinfo on Monday as he reflected on the path that has brought him to a World Cup semi-final.
Glenn's brother Dale, currently watching from afar, still can't believe any of this is real. They used to be absolute menaces, pretending the cutlery they had in their hands at the dinner table were cricket bats instead. They played together for New Zealand at the Under-19 level and they hope to play together again, following in the footsteps of the McCullums and the Marshalls.
"We were always very competitive in the backyard when we were growing up," Dale said. "The goal was always there to play big games at a World Cup. Especially for Glenn to be where he has got to now… It was more of a dream as opposed to thinking it would become a reality. I don't think either of us imagined where he would be right now. It's pretty cool to see that one of those dreams has come true."
It's been a long road. Opportunities at home were scarce. So Phillips had to expand his horizons. The break came in T20 cricket and has led to a situation where, for almost half of his career - 98 out of 218 matches - he has been representing teams outside of New Zealand. His performances as an opener in the Caribbean Premier League - he was its top-scorer (1147 runs) across a three-year period between 2018 and 2020 - finally gave him what he's always wanted, but with a small twist.
"West Indies came to New Zealand," Phillips said, "And I hadn't played for the Black Caps for a while and [coach Gary] Stead said 'you've got a lot of experience against West Indies players, and you're going to bat at four'."
This was three years ago, in November, just as the world was coming out of a pandemic. And Phillips spent a good portion of the time everybody had to spend in isolation building up his strength. Here's why.
"I was lucky enough to have a coach who went to the Youth Commonwealth Games. And he taught me a lot about sprinting and about fitness. And his concept was always the same - if it's between you and another player, and if you're significantly fitter than the other player [when] you have the exact same skills, it gives you an edge over that player. That has always stuck with me."
It also probably helps that he has a sibling rival. "We spend a lot of time together in the winter," Dale said, "Waking up at 5-6am to train in the indoor centre in Auckland. Then go to the track next door to do all the sprinting and running. We've always been competitive and that competitiveness kept us at the next level; always trying to beat each other."
In his first stint as a New Zealand cricketer, having to bat mostly in the middle order, Phillips averaged 15.55. In the second one, he broke the national record for the fastest T20 hundred.
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"I just went out there with a different mindset to the first time I attempted to bat in the middle order. I'd gone through a rigorous gym regime, coming out of Covid, so I felt stronger and I felt I could take on more boundaries, if I needed to, and I think that gave me the peace of mind to then combat middle overs as presented in T20 cricket."
On the very day that Phillips finally found his feet for New Zealand - scoring 108 off 51 balls - he was also seen taking flight, pulling off the kind of catch that gravity explicitly forbids. He did it again in the opening match of the T20 World Cup in 2022 and by that time he'd cultivated something of a signature celebration - he would turn around, face the stands, spread his arms out wide and do a little upwards nod.
"Yeah, that is a thing (laughs). It came from a team event we actually had for the Auckland Aces. I think, at one point, I did it without thinking about it and a lot of the guys said it looked like the 'Are you not entertained' bit from Gladiator and I don't know I just sort of rolled with it. It kind of goes with the entertainment factor, you know, if the crowd is watching and I've managed to do something spectacular, it's very fitting. And I guess the reaction of the crowd is the thing that gets me going and that's the reason I play - to effectively hear that, that cheer and roar when something amazing happens. Those are the moments that you remember for the rest of your life."
Phillips may get the chance to pad up his highlights reel on Wednesday when it will be his job as one of New Zealand's finishers to find a way to disrupt a bowling attack with the most wickets (85), the best economy rate (4.5), the best average (19.6) and the best strike rate (26.2) in the World Cup.
"It comes down to focusing on my process at the end of the day and understanding that there's a lot more time than I think," he said. "Understand my game plan and going 'okay, if this is how many overs there are in the tank, what do I feel is a good score here?' Communicate with the boys who have batted before and taking all the information and then effectively putting it behind and saying, 'okay, I trust that my brain understands what it needs to do' and then try to be as calm and clear as possible when the ball is released.
"Ideally to have nothing in my mind at the point of time [of delivery] means I can make the correct decision for that ball, regardless of the situation. And committing to something as well is a big thing for me - understanding whether I commit to take a bowler down. It doesn't have to be every single ball going for six. I've watched a lot of Heinrich Klaasen recently - how he goes about things. There's an element of being extremely explosive but having the clarity of mind to play a shot through third man for four. So, for me, it's trying to have that clarity and calmness so that I can be attacking as well as making the right choice for the next ball that's maybe easier to hit than the one that's currently coming down."
At his core, Phillips is an entertainer, and now that he's part of a World Cup semi-final against India, he will be beamed live to millions of people - including Dale who will have his own challenge to face that day, playing for Otago against Northern Districts in the Plunket Shield. "Honestly for me," Phillips said, "it's about taking my mind away from personal worries or performance or I guess putting too much pressure on myself. To take focus off myself and give it to the externals around me; give it to the team, give it to the crowd and give it to my family. To leave an impression on those who are watching, ideally for the better."