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Following months of uncertainty, the Pirates and Bryan Reynolds agreed to an eight-year, $106.75 million extension, the richest deal in franchise history, that will keep him in Pittsburgh for years to come. The city of Pittsburgh can collectively exhale.

So, what now?

In signing Reynolds and third baseman Ke’Bryan Hayes to long-term extensions in back-to-back years, the Pirates are signaling that winning is possible during this current window. They’ve signed two players to the largest and second-largest deals in franchise history, and given their trajectory, there could be more on the horizon. 

“Well one, we’re not done. To a great degree, we’re just getting started," said Pirates chairman Bob Nutting. "I think we see that with the start of this season. We’ve played a handful of games. We’ve played very well. It’s a long season. We have a lot of season in front of us. So, to a great degree, we’re just getting started. I think today, we should focus on what we did today, which is a huge step for the franchise with Bryan. I’m confident we’ll have future steps as we go forward.”

With Hayes and Reynolds signed, which other Pirates could the team seek to ink to a long-term extension? There are three names that stand out: Mitch Keller, Oneil Cruz and Roansy Contreras.

Keller, 27, is the closest to free agency of the bunch. The right-hander still has two years of arbitration eligibility -- he signed a one-year, $2.4375 million deal with Pittsburgh in January to avoid arbitration in his first year of eligibility -- and stands to become a free agent after 2025.

Keller is building upon the foundation he laid during last year’s breakout season. In five starts this year, Keller is posting a 3.64 ERA with 30 strikeouts across 29 2/3 innings. He is currently in the midst of a stretch of four consecutive quality starts, a total that is tied for the league lead.

“I think the expectation with Mitch is we know every time he goes out, regardless of how many pitches he throws or how many innings he throws, that he's going to give us a good outing,” said manager Derek Shelton.

Cruz, 24, and Contreras, 23, on the other hand, are still in the relative infancy of their careers. Both Cruz and Contreras have three more seasons of pre-arbitration in ’23, ’24 and ’25, then have three more years of arbitration in ’26, ’27 and ’28. The Pirates, of course, have the option to sign them long-term well before they approach free agency.

In recent years, there has been an uptick in young players who have reached long-term extensions before they hit arbitration. A month and a half ago, for example, the D-backs signed Corbin Carroll to an eight-year, $111 million extension, despite Carroll having only played 32 Major League games at the time of the deal.

Cruz has teased his talent across the 98 Major League games he’s played thus far, totaling 19 home runs and 13 steals with a 108 wRC+. Along with the production, he possesses a set of raw physical tools that no one can match, holding the Statcast record for both hardest-hit ball (122.4 mph) and hardest-thrown infield assist (97.8 mph) while also boasting blazing speed.

Cruz improved at the plate as last season went along and was poised to show what he could do over a full season before a fractured left fibula and an injury to the syndesmosis that will sideline him for four months. Director of sports medicine Todd Tomczyk said earlier this month that the team does not expect the injury to impact his range. It remains to be seen whether the injury does or doesn’t affect the calculus of negotiations moving forward.

“We’re very confident this is not going to be a long-term injury that will impact things such as range,” Tomcyzk said. “There’s always a possibility of that depending on the hiccups of the rehab, but very confident that at this stage, there should not be obstacles … that should impact him long-term. Maybe initially, just as you works back from rehab, but not long term.”

Extending Cruz and Keller sometime this year would make sense, but the Pirates might be inclined to take a wait-and-see approach with Contreras, who has only pitched in 26 games (23 starts). This would fall in line with the industry-wide status quo; the majority of young players who get extended are position players, not pitchers. 

Contreras has pitched well in his limited time at the Major League level, posting a 3.84 ERA and 4.07 FIP across 119 2/3 innings, but this season will be his first opportunity to pitch wire-to-wire in the Majors. Last season, Contreras threw more than 100 innings (Majors and Minors combined) for the first time since 2019, and it will be worth monitoring how he performs as the innings pile up.

The right-hander has lost a couple ticks on his fastball and is currently hovering around 94 mph with the pitch after regularly hitting the high-90s early last year. While a bit concerning, Contreras is mitigating that loss with his slider, which has been one of baseball’s best pitches so far this season.

“That’s one of the things that’s been noticed,” said pitching coach Oscar Marin. “One of the things that we’re just trying to do is get back into a full routine. … He’s one of the guys that came into Spring Training and had to leave Spring Training [for the World Baseball Classic], then had to come back into Spring Training and then get built up. So, hopefully with the consistency of the season and his work and that five or six days when we have off-days that things will be right where it was before.”