Brandon Lowe, Pittsburgh PiratesBrandon Lowe/Photo provided by Eddie Provident

The 20th anniversary of one of the Pittsburgh Pirates’ most embarrassing moments passed unnoticed earlier this year. Not that the Pirates would want anyone to remember it.

The Pirates’ 2006 home opener was one of the worst days in franchise history. The Pirates had already lost six of seven games to begin the season and fell 5.5 games off the pace in the National League Central. Postseason hopes were essentially gone one week into the season.

The Pirates were booed during pre-game introductions and throughout an 8-3 loss to the Los Angeles Dodgers at PNC Park. I’ll never forget the beleaguered look on poor Jim Tracy’s face during his first post-game press conference as manager with the hometown media.

Yet the most embarrassing moment came after actor Michael Keaton threw the ceremonial first pitch and was asked about the Pirates’ lack of success and low payroll. The Pirates were coming off a 12th straight losing season in a streak that eventually stretched to 20, the longest run of futility in major North American professional team sports history.

Said Keaton: “For my money, that’s disrespectful. At some point, you either have to write the check or do something and not assume, well, we’re OK and, ultimately, the franchise is valuable, anyway.”

So, why dredge up a bad memory?  Simply because the Pirates need to heed Keaton’s advice this winter.

The Pirates haven’t been to the postseason since 2015, but they’re poised to contend in 2027, if they make one very bold and expensive move.

The Pirates need to re-sign second baseman Brandon Lowe as a free agent. He was the biggest reason they improved by 11 wins this year, going from 71-91 to 82-80.

Yes, the fans expected the playoffs this year because team president Travis Williams oversold the Pirates’ postseason potential at the end of the 2025 season. However, the Pirates wouldn’t have had a winning season if Lowe hadn’t hit 35 home runs, driven in 96 runs, played stellar defense, and brought much-needed professionalism to the clubhouse.

Re-signing Lowe won’t be cheap. Most MLB executives I’ve polled expect him to sign a three-year contract worth an average of $20-25 million per year.

Offering a 32-year-old free agent three years and $75 million isn’t something the Pirates would be comfortable doing. Owner Bob Nutting is extremely risk-averse, though general manager Ben Cherington convinced him to sign a nine-year, $140-million contract to shortstop Konnor Griffin this year, even though the 19-year-old made his major league debut less than a week earlier.

Bringing Lowe back does represent somewhat of a gamble. He is 32, and no one knows when Lowe might enter the decline phase of his career. However, Lowe takes his craft seriously and doesn’t seem to be affected by making big money.

With baseball’s collective bargaining agreement set to expire on Dec. 1, no one knows what the sport’s economic system will look like when next season begins. Nor is it clear what the ramifications of signing Lowe to a big contract would be for the Pirates.

However, history suggests that players will stand firm in CBA negotiations against a salary cap, the owners will cave, and things will end up pretty much the status quo.

Regardless of how the labor situation plays out, the Pirates need to sign Lowe. The franchise hasn’t won a division title since 1992, and its last postseason series victory came in 1979.

At some point, the Pirates need to have some pride and go for it. Bringing back Lowe would signal that the franchise seriously wants to win.

Maybe bringing back Lowe wouldn’t work. However, it would be nice to see the Pirates take some risk for a change.

As the man said 20 years ago, sometimes you got to write a check.

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