Pirates Should Consider Pursuing Longtime Rival Outfielder in Free Agency

The Pittsburgh Pirates fell short of making it into the playoffs in the 2026 season, but they did make some improvements.

The Pirates hold an 80-78 record heading into the final games of the regular season and are seven games out of the Wild Card spot. While they are eliminated, they are closing in on ending their 11-year playoff drought.

To become a playoff team next season, Pittsburgh should pursue adding a couple of quality bats this offseason. One player they should pursue is rival outfielder Ian Happ from the Chicago Cubs.

Happ is entering free agency after a solid season, as he slashed .224/.329/.416 with 24 home runs, 28 doubles, 68 RBIs, 88 runs, and a .744 OPS.

His average went down in the 2026 season, as his career batting average is .244, but he still hit for power, which is something the Pirates could use more of.

Brandon Lowe currently leads Pittsburgh with 34 home runs, but the next closest is Oneil Cruz with 20. Adding another power bat to the lineup like Happ could help the Pirates as they make a playoff push.

Signing Happ would also take away from the Cubs' lineup, which could help Pittsburgh have a shot at winning the NL Central. 

Happ's last deal was a three-year, $61 million deal with Chicago. He could earn a similar average annual value or slightly less due to a down year in 2026. However, the Pirates may be able to get him on a shorter, team prove-it deal.

The 32-year-old was born in Pittsburgh, and if the Pirates can land the hometown slugger and retain key free agent Brandon Lowe, it would be a couple of major steps toward building a strong lineup capable of getting the team into the postseason.

Pittsburgh will also need their star starter Paul Skenes to have a better season in 2027. Skenes was dominant in his first two seasons in the MLB, winning the Rookie of the Year Award in 2024 and the NL Cy Young Award in 2025. 

His numbers dipped in 2026, with an ERA of 3.91 entering his final start of the season, after posting an ERA under two in each of his first two seasons.

If Skenes can have a bounce-back year and the Pirates are aggressive in the offseason by adding a bat like Happ, it could help them make the next jump and end their long playoff drought.