Even with new contract, Milwaukee Bucks' Bobby Portis vows to keep underdog mentality

Technically, Bobby Portis has been a free agent four times.

In 2019, he signed with the New York Knicks. In 2020, of course, he signed with the Milwaukee Bucks. After an opt-out following the championship run, he returned for another season last year. He opted out again, setting the stage for the first long-term contract since his rookie deal in Chicago.

This free agent spin was a bit different, one Portis called an honor to experience, as handfuls of teams reached out to him early and wanted him on their rosters. But for the third time, Portis agreed to return to Milwaukee on a four-year, $48.5 million deal with the Bucks – a contract that became official Wednesday.

It sets the stage for him to stay in one city for the longest period of time in his professional career. 

But it doesn't mean he's going to settle.

“My mindset is I’m never really secure," he said Thursday after a workout. "I’m always the underdog mindset, any day, anything can change. Just because they love you today they might not love you tomorrow. That’s always been my mindset in this league.

"My vets taught me that at an early age, my agent taught me that at an early age as well coming into this league. My mindset is always going to be that someone is trying to take my spot and I have to go hard each and every day to show why I’m worth what I’m worth. That’s that.

"But it is kind of cool to finally have some security in the league and finally be in a place where you want to be and can still continue to try to win. You don’t really get all those all in one so to be here is great for me, to get the chance to compete each and every night, play meaningful basketball games and I think that’s what I thrive on is playing in meaningful games and not just playing to play.”

And after two seasons of saying he turned down more lucrative offers to sign and re-sign with the Bucks, the team offered about the most they could under the “early Bird rights” they held on him. But there was more, too. HoopsHype, a USA TODAY property, reported there is a 15% trade kicker in the deal should he be dealt and the fourth year is another player option.

“I think it’s cool, man, to have an organization that believes in you, have an organization that likes you," Portis said. "It’s not always like that for players in the league. Opportunity is everything in this league and sometimes guys can play but they never get a chance to show what they can do because of the guys in front of them, because of the situation they’re in or whatever the situation is.

"So for me to be able to come here, impact winning – that’s the biggest thing that I love to do – and be on a championship team and have a front office that believes in me, have teammates that trust in me to go out there and by myself on a nightly basis, have a fan support that’s like no other that I’ve experienced in the league, it’s great.

"Especially with them doing everything they can to essentially bring me back, I tip my hat to them. That’s a lot of respect I have for (general manager) Jon Horst and his staff.”

But if there was a thought the 27-year-old might head out immediately and celebrate his new contract, he put that to bed immediately by getting in several workouts during the holiday week at the team’s practice facility.

“I ain’t got nothing to celebrate though, man," he said. "I work hard. I work on my game. That’s what I love to do in the summertime. I dedicate my time all to basketball.

"Ever since I’ve been here I watch film more on some of the guys I want to emulate my game on, the Kevin Garnett’s of the world, the Rasheed Wallace’s of the world, just some of the things they do with their game to be a complete basketball player.

"Obviously I’m glad that the Bucks chose to bring me back and we met at terms and this and that, but I’ll always feel like I’ve got something to prove. Obviously I’m happy that I got a chance to build generational wealth for my family, but still a lot of work left to do and there’s not time or need to celebrate.

"I work hard, I work on my game. I always knew one day it would always come back around if I just believed in myself, believed in God. Obviously when you’re a young player in this league, I turned down a big, lucrative deal before and people called me crazy and I always knew it would come back one time, I just had to keep working.”

Portis’ re-signing was the headlining move of the Bucks' offseason, as Horst and his staff doubled down on the roster that won 51 games last year and advanced to the Eastern Conference semi-finals.

The Bucks also brought back free agent guards Wesley Matthews and Jevon Carter and center Serge Ibaka and Pat Connaughton opted into the final year of his contract.

The newest faces were veteran forward Joe Ingles, who signed a one-year deal, and first-round draft pick MarJon Beauchamp.

“Just think our biggest thing is just staying healthy, building our camaraderie, guys getting outside of themselves during the regular season," Portis said. "I think we need to focus on that a lot because when the playoffs come, playoff teams take away your one or two things that you do really well, so you have to go to your third or fourth option.

"I think we need to focus on that a lot more, especially with some of the guys – in case, knock on wood, hypothetically speaking, if anybody goes down – guys will be ready to do things that they’re not normally accustomed to doing. I think that’s a big thing now for our team going forward. Then the biggest thing is just building up on camaraderie on a whole, being connected on and off the court."