On 2/22/24 the Pirates made it three years in a row, locking up All-Star Mitch Keller to a four-year extension.  Previously, the Pirates had locked up Bryan Reynolds and Ke’Bryan Hayes on long-term extensions; however, the last long-term contract the Pirates gave to free agents was in 2016, when Ivan Nova signed a 3-year twenty-six-million-dollar contract. Why? What is causing the Pirates to hand out extensions to their own players but leaving them incapable of signing Free Agents? Unless it is to a one-year contract. There are a few potential reasons for this and they may not be liked.

Extensions are a great way to not only show loyalty to your young players but also a way to lock up talent cheaper than on the open market. This makes them ideal for small-market teams like the Pirates. It is also good for owners who prefer to put as little money into the club as possible while still maximizing revenue. Fans want to see their favorite players stay and play for their teams and this is a good way to manage that. Pirates have done this in the past to a mixture of success. Andrew McCutchen signed a team-friendly contract extension and was worth every penny.  They did the same with Starling Marte to almost the same level of success. Gregory Polanco signed one as well but was not nearly as effective as the others afterward.  Jose “Neck Lips” Tabata also signed a contract that could have kept him with the club through 2019, although he barely made it past the infamous Scherzer No-No in the middle of the 2015 season. So, while some extensions make teams better or look like geniuses, some can have a more debilitating effect on the franchise. Therefore, it is very important for teams to not only lock up their young players to reasonable extensions; however, they need to be careful about which players they sign and for how much.

Free agency is truly the Wild West of old, with gun fights, saloon gambling, and posses being rounded up to go after outlaws. Or at least it was. This offseason, things were more measured. There are still several very good free agents without contracts, though the closest thing we had to a posse was people trying to track planes Ohtani was on. Free agency, however, is a great place to build upon the core a team has started to put together. This has been the bane of Pirates fans’ existence for many years. The current front office has only been signing players to one-year contracts, and usually trading them before they are up.  Plenty of teams have started signing free agents long-term a year or two before the team plans to be competitive. This allows the new players to not only assimilate to their new environment but also to build good relationships with their teammates and coaches. This is the approach the Pirates front office has been failing at year in and year out. Had they signed an FA starting pitcher last year to a multi-year deal, their rotation would look much better today than it does. If they had been able to lure an SP in this offseason, fans would be much more at ease than they currently are.  It was rumored, if not suggested, that the Pirates made such offers to Sean Manaea, Yariel Rodriguez, and Shota Imanaga but failed to sign any of them. This is more than likely due to the reputation the Pirates have in the baseball world, which was made worse by a recent article published by the Athletic. Players have to want to play for you or you have to grossly overpay for their services. The former hasn’t happened for the Pirates since 2016, and the latter probably will never be an option. Perception can change, however, as can how teams operate.

Extensions will remain the bread and butter of the Pirates, and all small to mid-market franchises; however, in the case of the Pirates particularly, to make a complete team they will need to find a way to encourage free agents to come to Pittsburgh. One way to get this to occur is to build a culture that free agents want to be part of. This will include starting to win more games and be playoff and division contenders. The other way will be to spend, spend, spend. The Beatles might have sung “Money can’t buy you love” but if Billy Bean taught us anything, it can buy you wins. If the Pirates want to make a quick culture change and prove they want to win, as well as prove that they are willing to spend money on free agents, now is the time. Bob “Pay for the Gym Out of the Player Salaries Fund” Nutting can do fans a favor and either “Nut Up” or “Shut Up.” Either “Shut Up” and stop selling how he “wants his team to win,” and “this might be the group to do it,” and “we will spend when it is time,” OR “Nut Up” and spend some long-term money on a free agent that can get this team to the playoffs. Jordan Montgomery could be that player, Blake Snell could be that player, J.D. Martinez could be that player. As discussed, here, there is no reason that the Pirates cannot spend like the Reds or the Brewers. “Nut Up,” Bob, and bring the fans what they want, or to quote a phrase from the Wild West “Get the f*** out of dodge.”

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