With the 2023 Major League Baseball regular season winding down, Bryan Reynolds, the Pirates starting left-fielder, is having a pretty good all-around year.

Reynolds is currently batting .272 with 143 hits, 21 home runs and 75 RBI. He has an on-base percentage of .333 and an OPS of .804. While not his best season, Reynolds’s final numbers will look similar to the ones he posted in 2021 when he batted .302 with with 24 home runs and 90 RBI.

Reynolds was the National League’s starting centerfielder in the 2021 MLB All-Star game. It was quite the season for a young player who had a bit of an up-and-down career since the Pirates acquired him in a trade for Andrew McCutchen in 2018.

The sky seemed to be the limit for Reynolds following his breakout year in 2021, but after having a bit of a down season in 2022–including a .262 batting average, 27 home runs and 62 RBI–which was just two years removed from the dreadful stat line he posted during the pandemic shortened 2020 campaign–.189, seven home runs and 19 RBI–one had to wonder what kind of player he really was.

Was Reynold’s a poor man’s version of McCutchen, the 2013 National League MVP and one of the game’s best players during his prime years, or was he a poor man’s Jason Bay, a two-time All-Star for the Pirates who posted 139 home runs and 452 RBI during his four-plus seasons in Pittsburgh? While Bay was one of the better all-around players in baseball during his prime years, he was never up there with the best of the best.

The same could be said for Reynolds coming into 2023, only to an even lesser degree.

No matter who Reynolds was a poor man’s version of, there was no doubt he was the Pirates best all-around player (at least until Oneil Cruz hopefully reached his potential); he was also getting to the point of his career where questions were being asked about his future with the organization.

Would the Pirates, coming off three-straight last-place finishes, try to sign Reynolds to a contract extension, or would they go the more familiar, and frustrating, route and trade the 28-year-old for some prospects?

The scuttlebut in spring training was that Reynolds and the Pirates were talking about an extension but were far apart in years and/or money.

Reynolds made a strong case for himself right off the bat by having an April to remember; Reynolds batted .323 over the first month of the season, while smacking five home runs and driving in 22.

Perhaps like Rod Tidwell and the Cardinals in the football/sports agent movie, Jerry Maguire, Reynolds’s hot start left the Pirates no choice but to do what they had never done before: Sign a player to a $100-plus million deal. And on April 25, it was announced that the two parties had agreed upon an eight-year contract for $106.75 million.

Needless to say, it was the richest contract in Pirates history and perhaps a sign that this notoriously frugal small-market organization was willing to go out of its comfort zone when it had a good, young player and a team that was ready to win in the not-so-distant future.

How did Reynolds immediately respond to his new deal? By going into a horrific tailspin over the next three months. Reynolds posted batting averages of .242 in May, .268 in June and .200 in July. He also combined for seven home runs and 26 RBI over that same three-month period.

Yikes.

Reynolds returned to his April form in August and batted .288 with seven home runs and 16 RBI. Reynolds remains pretty hot in September and, again, will finish with some pretty decent all-around numbers.

But it sure doesn’t seem like Reynolds has been much of an impact player for the Pirates, a team that is currently 10-games under .500.

Then again, maybe Reynolds was never going to be anything but what players of his going rate usually are.

When you compare Reynolds’s annual salary of $13-plus million to some of the game’s highest-paid sluggers–including the Yankees Aaron Judge, who earns $40 million a year–perhaps the Buccos are getting the maximum bang for their bucks.

I have no way of knowing this, but I’ll just bet the Pirates were hoping they caught the same lightning in a bottle that they did in 2012 when they signed McCutchen to a six-year, $51.5 million contract extension, a deal that would feel like a steal by 2013.

To reiterate, it doesn’t look like Reynolds has Cutch’s clutch gene, nor the latter’s ability to be one of baseball’s best players during his prime years.

Again, though, it’s hard to blame Reynolds when you compare his production and salary to MLB’s best and highest-paid offensive players.

In a lot of ways, Reynolds and his new contract remind me of Jason Kendall and the deal he signed with the Pirates back in 2000. Kendall was a multi-time All-Star catcher for the Pirates after making his debut in 1996 and was one of the best in the game at his position. There was growing pressure for the cash-strapped and constantly-struggling Pirates to sign their talented and popular All-Star to a contract extension, which they finally did, to the tune of six-years and $60 million. But while Kendall would continue to be one of the game’s best catchers and one of the Pirates best players over the next few seasons, he just never had the kind of impact that could lift his struggling franchise from the doldrums and lead it into contention.

Much like with Reynolds, Kendall’s contract extension was a show of good faith from the Pirates to their fans, but it ultimately didn’t lead to anything tangible on the baseball diamond.

Signs of good faith are nice and all, but the fans want results at the end of the day.

I guess the moral of the story is this: If a guy like Bryan Reynolds is your best player, what’s the point of offering him a contract extension? Sure, he might be your best asset, and he might agree to the going rate for players of his caliber. Yes, signing him to a new deal might be a good public relations move, and one that will lead to an uptick in ticket sales.

Having said all of that, those good feelings will soon disappear if that player doesn’t lift your organization up.

And he’s probably not going to lift your organization up.

It’s yet another dilemma facing the small-market organizations of Major League Baseball.