The Cincinnati Reds are entering an off-season full of looming free agency decisions. While facing pressing on-field concerns that could hamper future postseason hopes. In what could be Cincinnati’s most significant off-season of the 2020’s.

The Reds have nine free agents going into this offseason. Right fielder Nick Castellanos and center fielder Delino DeShields Jr. Along with recently added second baseman Asdrubal Cabrera. Catchers Tucker Barnhart and minor leaguer Rocky Gale. Along with pitchers Wade Miley, Michael Lorenzen, Mychal Givens and Justin Wilson.

Castellanos is the Reds’ most high-profile free agent. Emerging from an All-Star season with 100 runs batted in. Along with bringing an energetic flair to the team. Castellanos has two years left on his contract but has the opportunity to opt-out. Given the season he had, many expect him to opt-out and capitalize on that phenomenal season.

Barnhart, Castellanos, Miley and Lorenzen are the four the Reds would be wise to retain. Miley is fresh from a monumental season of his own. He threw a no hitter in May and emerged as a reliable part of the Reds starting rotation. Miley has a $10 million option with a $1 million buyout. While Lorenzen missed a long part of the season due to injuries. He is the closest the Reds have to a two-way player. 2022 could be a resurgent year for him that the Reds could get a boost from.

Barnhart is one of the most skillful catchers in the major leagues. Both from a defensive standpoint and as an unofficial pitching coach. With two Gold Gloves to show for his efforts. Barnhart has a $7.5 million option with a $500,000 buyout. The emergence of rookie catcher Tyler Stephenson will be a factor in how the Reds approach Barnhart. Cincinnati will be in a lucky spot if they can retain both. While Rocky Gale might be sent on his merry way to make room.

Cabrera, Givens, Wilson and DeShields Jr. are relative newcomers. Givens and Wilson were added by the Reds before July’s trade deadline. Cabrera was claimed off waivers from the Arizona Diamondbacks in August. Putting forth career lows in several categories. With two hits, a .077 batting and slugging percentage among other lows. DeShields Jr. was a September callup who spent most of 2021 in the minor leagues. Joining the Reds in August from the Boston Red Sox organization.

The areas of improvement the Reds need to focus on are mostly the same as last year. Cincinnati’s bullpen was mostly unreliable throughout the season. The Reds didn’t have a consistent center fielder either. Not having an everyday shortstop also hurt the Reds at times. While Kyle Farmer was able to step in as a reliable utility player. Farmer can’t reasonably be called upon to fill every gap in the lineup. Having reliable bench players will be key for the 2022 Cincinnati Reds.

There’s one question that sticks out going into this offseason. Will the Reds actually invest in the team after doing some shedding last year? COVID-19 rendered the Reds ability to make big additions last winter. Though some Reds fans would argue the front office was just being cheap. It would be surprising if the Reds are big spenders this offseason.

The Reds are approaching the 50th anniversary of one of their most pivotal off-seasons in franchise history. In November 1971, the Reds traded Lee May, Tommy Helms and Jimmy Stewart (not the actor) to the Houston Astros. In exchange for Joe Morgan, Ed Armbrister, Jack Billingham, Denis Menke and Cesar Geronimo. The trade could be considered the most consequential in Reds history. Bringing on players that went on to be significant parts of the Big Red Machine.

This off-season might not be as monumental as the 1971-72 off-season for Cincinnati. Though it could be the most monumental of the 2020’s. Depending partly on whether Cincinnati convinces Castellanos, Barnhart, Miley and Lorenzen to stay. Along with having enough roster depth to endure a big injury. Something the Reds didn’t have in the last six weeks of the season. After losing All-Star outfielder Jesse Winker to a season-ending injury. Along with defensive phenom outfielder Shogo Akiyama.

The Reds already have a contending team. Without bullpen improvements, their 2021 All-Stars or bench players that can hit. They risk squandering their postseason hopes again next year.