Cartwright has been a member of the Pride since its entry into the revamped national league seven years ago.
In fact, he's the only foundation member left in the team that travels to Christchurch this weekend for the second round of the league.
"I'm the last of the originals, which feels a bit strange," Cartwright told the Otago Daily Times.
Cartwright (29), who is engaged to Esmay Sutherland and gets married in August, grew up in Invercargill and has been playing softball since he was about 5.
He bats in the crucial No 3 spot in the Southern Pride's batting roster and plays centrefield.
He said he didn't strike the ball as well as he would have liked in the opening round two weekends ago but hoped he was coming back into form.
It's a motley crew, the Pride. Cartwright and Daniel Tarapi are the only players based in Dunedin, Chris Anderson travels from Alexandra, and other players come from Nelson, Blenheim, Wellington and Auckland.
"It's quite tough. We basically don't get to train as a team," Cartwright said.
"We're expected to do our own work, so we go to the gym and have a hit around at the park. It's not like the other top teams who are training together for months.
"That obviously makes it a lot more difficult."
Cartwright is one of the most experienced men in the Pride but even he can't match the career of Marty Grant, the great Black Sox pitcher who is based in Nelson as Southern's player-coach.
"Marty's been part of the Black Sox basically since the start of their great run winning the world titles," Cartwright said.
"He's been there and done everything. And there's huge pressure on him as the pitcher, but he handles it really well."
Cartwright, a human resources adviser at the University of Otago, said the Pride had put itself in a position to make a rare appearance in the national league finals this season.
After losing every game last year, the Pride won two of its five games in the opening round this year.
"We've got good pitching and when we hit the ball, we go well," Cartwright said.
"When the league started we always had good defence but we never scored enough runs, apart from one year when we had a couple of ring-ins.
Then we had a spell where we were hitting the ball but not coming up with the pitching or defence to shut teams down.
"This year we've got Marty on the mound and we've also got the potential for really good hitting."While the men need to win immediately to get back on track in Christchurch, the Southern Pride women will be slightly more relaxed about their weekend in Wellington.
They won two of their four games in the opening round and had a 2-0 loss to Auckland, indicating they can match it with the other teams.
Southern Pride
National league softball
Draw for games this weekend.-Men (in Christchurch)Today: v Hutt Valley, 11am; v Canterbury, 1pm; v North Harbour, 5pm.
Tomorrow: v Auckland, 9am; v Wellington, 11am.
Women (in Wellington)Today: v Auckland, 1pm; v Hutt Valley, 3pm.
Tomorrow: v Wellington, 11am; v Canterbury, 1pm.