North Shore Nine

In each of the last three seasons, the Pirates have given out extensions to good young players. On 2/22/23 the Pirates signed Mitch Keller to a 5-year 77-million-dollar contract. Last season, the Pirates gave Bryan Reynolds an 8-year 106.75-million-dollar contract. The first big extension came in 2022, when Ke’Bryan Hayes signed an 8-year 70-million-dollar contract, with an option for a ninth season.  After the Keller extension, there has been a lot of speculation regarding who will be next. This has led to a list of the usual suspects: David Bednar, Oneil Cruz, Paul Skenes, etc. But, what extensions make sense not only for the fans but for the Pirates Organizaiton?

To start, none of the “big” name players are set to be free agents after this season. The person closest to being a free agent is Bednar, who has two more arbitration seasons left, making him an FA in 2027. The next Pirates to be potentially hitting free agency would be 2029 with guys like Johan Oviedo, Colin Holderman, Jack Suwinski, and Cruz. But, which players make sense to lock up long term, and when would be a good time to do so?

David Bednar:

Bednar has been dominant for three seasons now for the Pirates, being named an All-Star the last two seasons; however, he has also lagged down the stretch each of those years, as well as spending time on the DL in August or September in ’21 and ’22. Now, it might be a matter of more careful usage so that Bednar doesn’t lag moving into the dog days of summer. However, it could also be something else, like a general lack of gas in the tank.  Regardless, fans get held up on the fact that he is a hometown kid. It is great when he is presented with a 30 rack of IC Light whenever he makes the All-Star game.  Furthermore, if it was an award/contest, Bednar would surely be the “Pirate You Would Most Like to Have a Beer With.” When it comes down to whether or not he is worth extending, however, the answer is sadly no.

When you look at what closers are currently making, it would take a massive hometown discount to keep Bednar around. Ryan Pressly signed a 2/30 contract before last season. This offseason, Josh Hader signed a 5/90 contract. Bednar has been as good as these players over the last few seasons, but there is no way the Pirates can pay their closer more than $15 million a season. While it will kill Pirates fans, the best bet is to trade Bednar at the deadline or over the next offseason. Now, that is dependent, of course, on the Pirates, sadly, being out of contention or having another player prove that they can take over the closer role. But if those two conditions are met, the front office must act like the Pirates of old and go forth and plunder a farm system.

Oneil Cruz:

Cruz entered 2022 as high on a Pirate Fan pedestal as is humanly possible. He was coming off an impressive rookie campaign and was looking to be the next 20/20 or even 30/30 Pirate player. Unfortunately, Cruz broke his ankle on an awkward slide into Homeplate in his 9^th game of the season. Due to this, he missed the remainder of the season.  However, he comes into spring training in 2024 looking healthy and ready to get back on track. Does this mean the Pirates should offer him an extension? Again, the answer is no, but in the form of not-quite-yet.

The Pirates will need to see if Cruz is healthy. Also, they need to see if there are any lingering issues from the injury that sidelined him for a season. If he is healthy, and if he is able to stay injury-free, then the answer does become a resounding yes, they should consider an extension. Now, that is also dependent on him playing like he had in his rookie year, or playing better than his rookie year. He has five years left before free agency, so there is truly no rush unless the goal is to try to save money. But if the Pirates are smart—and not many would take that bet—they will wait to ensure he is back to form. Then, it would be prudent, if Cruz is willing, to lock him up long-term and keep him with the existing core. Cruz has the potential to be the lynchpin of this young core the Pirates are trying to build.  If he plays like he expects himself to, and the fans hope that he does, then it makes sense, to quote KGB from Rounders, to “Pay him. Pay that man his money!”

Johan Oviedo:

A name that might not be tossed around in extension talk is Oviedo’s, in large part due to the fact that he is on the DL for the year with a major injury. However, since coming over from St. Louis, Oviedo has been very good for the Pirates. In the ’23 season, he matches up after a fashion to a certain pitcher named Mitch Keller. Now, Keller was clearly a better pitcher when it comes to strikeouts and limiting walks—as well as FIP and WHIP—but they are maybe not as far off when you consider their ages and experience. If you compare their respective 4^th seasons the only area that Keller is better than Oviedo in remains walks and ERA.  However, it should be noted that in this case, Keller threw 18.2 fewer innings so there could be some wiggle room in those stats. The biggest issue with Oviedo is the Tommy John surgery he just had and how his recovery will go.

Via MLB.com, it is estimated that >70-80% of those who go through Tommy John can return to baseball activities;  however, it is also reported that roughly 28-37% have the chance of another injury hampering them. If, however, Oviedo can come back as expected from surgery, and if he can return to form next season. Then it is possible the Pirates can investigate an extension. It is risky to extend someone who has had such a serious injury; however, many have been able to overcome it to pitch very well in the majors. Jacob deGrom, Justin Verlander, Shohei Ohtani, John Smoltz, Stephen Strasburgh, and fan favorite Dick Mountain have all come back to pitch well after Tommy John surgery. So, if Oviedo can return to or near enough to form when he pitches next season and can remain injury-free going into next offseason, then it could be worth it for the Pirates to investigate signing Oviedo to a contract extension, to lengthen his time in Pittsburgh.

Jack Suwinski:

Suwinski came out of nowhere in 2022, hitting 19 home runs and putting up a 1.1 WAR. He followed that up in 2023 with 26 home runs and a 2.2 WAR. He took a good rookie performance and turned it into an even better sophomore showing. If he can repeat that again in his junior year, then the Pirates should prepare that checkbook. Jim Rosati has already staked his hot take of the season, stating that Suwinski will have a higher WAR at the season’s end than recently extended Bryan Reynolds.  If that is the case, or even if they are close to the same in terms of WAR, then there is no reason for the Pirates not to attempt to extend Suwinski.

A lot of this will depend on the bat that Suwinski swings.  While he was the starting Centerfielder last season, he wasn’t the best CF in the MLB. He might be best suited at one of the corner outfield spots if not DH. In his career, he has a negative defensive run saved above average in both CF and RF, though has a positive number in LF. Regardless of the defense, if his bat continues to progress, he could end up a player who hits 30 home runs or more a year. A big part of that will be him being able to control his dismal periods at the plate, meaning fewer long slumps and generally poor at-bats, if he can show that those periods are less pronounced this season. Also, if he is again able to outperform his stats from the previous season, as he did last year, then the Pirates should easily begin the discussion to keep him around as part of this young core.

Colin Holderman:

There might not have been a pitcher last year that Pirates fans white-knuckled more than Holderman. He appeared in 58 games for the Pirates last season, giving up 0 runs in 46 of those games, and only 1 run in 5 of those games; however, in the other 7 appearances, he gave up a total of 19 earned runs. On the plus side, he managed a career-high in SO/9 and a career-low in BB/9. Though, on the other hand, he gave up the first home runs of his career, giving up 4 across his appearances. If Holderman can manage to keep those BB/9 and SO/9 similar, or even improve them further, it will go a long way. Furthermore, if he can stop the Dr. Jeckyll and Mr. Hyde approach that he had last year, it will cement him as a relied-upon member of a very strong Pirates bullpen.

If he can manage these things the Pirates might be interested in seeing if an extension could be in the cards.  The potential comps here would be Trevor Stephan of Cleveland who signed a 4/10 extension or Pete Fairbanks of Tampa Bay who signed a 3/12 extension. Neither player was a closer for their respective teams, and both pitched similarly. Technically, Holderman pitched roughly over the last two seasons, and all three are of the same respective age and experience. Would the Pirates entertain such an extension? Absolutely, even if you get the same pitcher you had last year, an extension similar to either of those other relievers would be a good deal for the Pirates.

Paul Skenes:

Pirates fans have, at times, an unhealthy obsession with their prospects, especially those taken 1:1 in the draft.  Though that is the case with most fan bases, and there are plenty out there at are worse (looking at you Yankees fans!), Skenes very well might be the liberator prophesized to save the Pirates from their World Series droughts. But fans need to pump their brakes, and not because they see a tunnel approaching. Skenes has pitched all of 6.2 innings of professional ball and hasn’t become accustomed to pitching every fifth day as of yet. Considering the already discussed track record of pitchers rushed to the majors, here, it makes too much sense to wait and see what Skenes can and will do. There is no reason to look to extend Skenes already, be patient and pray that the Pirates have the money to do so when the time is right.