5 starters the Reds could trade for and immediately sign to a contract extension

Might the Cincinnati Reds follow their own blueprint from the 2018-19 offseason?

Seattle Mariners pitcher Logan Gilbert
Seattle Mariners pitcher Logan Gilbert / Dustin Satloff/GettyImages
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In January of 2019, the Cincinnati Reds pulled off a trade for then New York Yankees starting pitcher Sonny Gray. The Reds acquired Gray and Reiver Sanmartin in exchange for infield prospect Shed Long and a competitve balance pick.

Once the trade was finalized, the Reds immediately inked Gray to a three-year contract extension. The trade, combined with the new deal, gave Cincinnati a frontline starter with cost control for the next several seasons.

With so many young prospects in the farm system, a wide-open payroll for 2024, and a need for starting pitching, might the Reds make a similiar deal this offseason? If so, who might Nick Krall and the Reds front office have in mind?

1. Reds could trade for Royals RHP Brady Singer & sign him to an extension

There were whispers around the MLB trade deadline that the Cincinnati Reds were targeting Brady Singer. Might the Reds and Kansas City Royals reengage in trade talks during the offseason?

Singer is former first-round pick who just turned 27 years old. The right-hander started 29 games last season and posted a ground ball-rate near 50-percent. Both of those factors should bode well for a team like the Reds who are looking to get some length out of their starting rotation while also keeping the ball on the ground.

Singer's ERA, however, has not pretty. The No. 18 overall pick in the 2018 MLB Draft owned an eye-popping 5.52 ERA in 2023 after posting an ERA of just 3.23 the year prior. The past two seasons combined have seen Singer record a collective ERA of 4.40 and an xFIP of 3.80 according to FanGraphs.

Brady Singer is not a strikeout artist, but he does a fantastic job of keeping the bases clear. Singer owned a walk-rate of just 6.3-percent the past two seasons and 2.42 walks per nine innings pitched. Singer has the makings of solid, middle-of-the-rotation option.

2. Reds could trade for Mariners RHP Logan Gilbert & sign him to an extension

If there's a big fish in the pond, Logan Gilbert is it. The Seattle Mariners and Cincinnati Reds have been frequent trade partners the past two seasons and that familiarity could lead to a potential deal during the offseason.

There's no need for the Mariners to trade Gilbert, just like there's no need for the Reds to trade Jonathan India. But, if the right deal presents itself this offseason, Jerry Dipoto is no stranger to making trades.

The Mariners already have a soild 1-2 punch atop their starting rotation witth former Cincinnati starter Luis Castillo and right-hander George Kirby. Seattle also has Bryce Miller, Bryan Woo, and Emerson Hancock.

Gilbert is entering his first year of arbitration eligibilty, and seems to be just scratching the surface of what his potential could be. The past two seasons, Gilbert has eclipsed 185 innings pitched and owns a collective-ERA of 3.47.

Gilbert will not come cheap; both in terms of a trade and what he'd expect in a contract extension. But if the Cincinnati Reds are intent on adding a top-shelf starter, there might not be anyone better (who is available in a trade) than Logan Gilbert.

3. Reds could trade for Dodgers RHP Walker Buehler & sign him to an extension

Walker Buehler, unlike Sonny Gray, never played under the tutelage of Derek Johnson while he was at Vanderbilt University. But those Vandy ties run deep, and the Cincinnati Reds would love to have a frontline starter like Walker Buehler in their rotation.

Buehler, of course, would come with a major red flag. The right-hander underwent a second Tommy John surgery last year and needed surgery to repair a flexor tendon. While there was some hope that Buehler would return to the mound in 2023, after just one rehab start, he was shutdown for the rest of the season.

The Dodgers are going to be one of the more interesting teams to watch this offseason. LA is obviously in the mix for Shohei Ohtani, and also have Clayton Kershaw entering free agency once again.

The Dodgers are also likely to part with Julio Urias, Dustin May underwent surgery this past July, and Tony Gonsolin underwent Tommy John surgery in August. Will the Dodgers hang their hat on Buehler coming back in 2024 or look to part company this offseason.

Buehler will be a free agent after next season. From 2019-2021, Buehler was one of the best pitchers in the National League with a 2.89 ERA and 469 punch outs during those three seasons. Twice during that timeframe, Buehler finished in the Top 10 of the NL Cy Young vote. This is the quintessential high-risk/ high-reward move.

4. Reds could trade for Pirates RHP Mitch Keller & sign him to an extension

It's not very often that you see two teams make a trade within the division. However, the Cincinnati Reds and Pittsburgh Pirates did pull off an intra-division trade involving Kevin Newman and Dauri Moreta last offseason.

But when you're talking about a player as talented as Mitch Keller, things get much trickier. While the balanced schedule has seen teams play fewer games against their division rivals, trades within the division just don't happen very often.

When it comes to Keller, there's been talk of the Pirates looking to extend the right-hander, and with good reson. Keller can fill up the strike zone, and had over 200 Ks in 190 innings pitched in 2023.

While his ground ball-rate creeped up slightly in 2023, in 2022, that number was sitting at nearly 50-percent. Every Reds fan knows that keeping the ball on the ground while pitching in Great American Ball Park is a very wise strategy.

As stated early, swinging a trade within the division is difficult. Because of that, the Pirates would undoubtedly overvalue Mitch Keller and likely ask for more in return. But, if Keller fits the profile of what Cincinnati is looking for, it could be worth having a conversation with the Buccos.

5. Reds could trade for White Sox RHP Dylan Cease & sign him to an extension

Okay, we've finally come to the name that everyone is Reds Country will be clamoring for, and has been since the MLB trade deadline. Yes, Dylan Cease could certainly be an upgrade for the Cincinnati Reds pitching staff. The problem is, everyone and the brother is going to be gunning for Cease.

The starting pitching market isn't going to be overflowing with top-flight talent. Aaron Nola, Blake Snell, and Jordan Montgomery will probably be the top names that high-dollar franchises will be looking to add this winter.

But with the Chicago White Sox in freefall after last season's disaster, it's very hard to see the South Siders holding on to any player other than Luis Robert. With that mind, Cease could be had by the highest bidder.

Will that be the Reds? Cincinnati's farm system is loaded, and with plenty of young players who would no doubt tempt the White Sox to make a deal. It's not so much a matter of if the Reds have what it would take to make a deal, but rather would they be willing to pay the high price?

Dylan Cease is a terrfic pitcher who owns a four-seamer in the mid-to-high 90s. The right-hander struck out more than 27-percent of the batters he faced in 2023 and has started over 32 games the past three seasons.

Cease is just 27 years old and under team control for two more seasons. But if the Cincinanti Reds made this type of trade, it would be essential to lock up Cease for the foreseeable future.

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