
The Tigers and Orioles Have the Rare Chance of a Win-Win Trade. It's Time for Them to Make it Happen.
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With the trade deadline right on the horizon, plenty of teams will have the annually difficult decision to make on whether to buy, sell, or stay put with what they have. We're generally discussing players on expiring contracts when it comes to trade candidates, guys teams may be losing to free agency anyway that they might as well get something out of from a team that wants to compete that very season. It's why Detroit Tigers ace Tarik Skubal is such a rare trade candidate this time of year, as Skubal not only won't be hitting free agency next season, he's got 2.5 years left under contract no matter where he's playing. That leaves Skubal's trade value exponentially higher, giving the Tigers the chance to get far more out of him than your average rental since not only will a team be add a sure-fire ace to their roster, they'll have him for another two years after this one. And while it might be a tough move to make, and understandably might leave you second-guessing yourself a lot if Skubal goes on to win the Cy Young and stays healthy these next few years, this is something Detroit needs to go through with.
Life hasn't been easy for the Tigers this last decade, as since their glory days back in the early 2010s, they've missed the postseason in nine straight seasons, tied for the longest drought in the MLB right now. After a number of years towards the bottom of the league 2024 has produced more optimism than most in Detroit, and they're playing their best baseball of the season at the moment having won 11 of their last 14 games to pull within one game of .500. While it's been a fun couple weeks for Tigers fans, and I'm sure that series win over the Dodgers felt good, let's get real about their situation. The offense is still a liability, far too much for them to make up the ground necessary to compete in the wild-card race. Riley Greene is a great young player and the pitching staff has been strong, but there's still a long way to go before this team is any sort of a threat in the American League. Even with a strong farm system slowly working its way into the bigs, expecting this team to be where it needs to be to justify Skubal within 2.5 years is far too wishful thinking and has the potential to backfire tremendously for Detroit. Skubal's agent Scott Boras has a track record not having his clients sign extensions, and he'll have the chance to set the new bar for left-handed aces once he hits the open market. Should Detroit like their chances of bringing him back when he hits free agency in 2026? They're not exactly a premier spot for free agents and have been one of the worst teams in baseball over a decade-long sample size, and we know there's going to be a handful of teams lining up to offer Skubal just as much, and very possibly more once he hits free agency in two years. After what would be seven years in Detroit by that point, I have my doubts on their chances at re-signing him. At this moment in time, Skubal's value will probably never be higher. Since Skubal returned from flexor tendon surgery last July he's been one of the best pitchers in baseball by any metric, now the AL Cy Young favorite with an AL-best 2.34 ERA plus a 0.919 WHIP and 178 ERA+. The Tigers aren't forming a championship window or anything close to it by 2026, so all keeping Skubal around is doing is lowering his trade value for a team whose ceiling is a wild-card spot, when even that is something that hasn't been done in 10 years. They need to strike when the iron is hot - it can't possibly get much hotter - and cash in on one of the massive packages a team will throw at them. There's one team that particularly comes to mind, one with the personnel to do it and a potentially hand-in-glove fit for Skubal.
The Tigers have held firm that they aren't interested in dealing Skubal, and whether they stay true to their word or not, there's still going to be contenders hopeful Detroit will at least hear them out. Plenty of teams may feel adding the consensus top left-handed pitcher in baseball would be the missing piece towards a championship roster, and I can confidently say that the Orioles should and probably do feel such a way. Baltimore has been decimated by pitching injuries this season with Kyle Bradish, Tyler Wells, and John Means three of their starting pitchers already done for the year, though they've been playing at a high level even despite that and remain considered one the MLB's legitimate World Series contenders. Baltimore's pitching largely let them down in last year's ALDS and they went out and got a stud in Corbin Burnes last offseason to address that, the first major move under their new ownership that showed they were willing to get aggressive for the chance to win, a mentality that had really gotten away from them over the years to the widespread dismay of the fanbase. Burnes' addition has been especially crucial with all the pitching injuries, and they still feel like they could use another arm to really solidify this rotation as championship-caliber. Luckily for them, for the right price Tarik Skubal should be movable, and Baltimore's top-ranked farm system should give them the assets to make it happen. So much of the Orioles' young talent is already tearing up the majors but there's still plenty left behind that could go a long way in a spot like this. Jackson Holliday tops that list, the 2022 1st overall pick and undisputed top prospect in baseball, and while Detroit has made it abundantly clear the great lengths it'd take to build a package worthy of Skubal, you'd have to think throwing Holliday in there becomes a massive game-changer. Now this might be tough to sell Baltimore on, as not many prospects in recent memory have been touted higher than Holliday and at 20 years old with six years to go under team control, the value doesn't get much higher. But Baltimore can win this thing now, and there's no reason to believe they won't be right in the thick of things these next two seasons too, where Holliday is far from a given to be playing at a level capable of starting on a contending team. They've got a lineup filled with young talent that is only going to get better with age, and even without Holliday would still have a plethora of young prospects that should one day be contributing to a major league roster. It would be understandably difficult parting ways with a top prospect the whole league is expecting big things out of, but how much better of a hitter can Holliday really be than Skubal is a pitcher? Skubal might be the best pitcher in baseball, has 2.5 years of team control, and with a new regime in Baltimore that has been adamant they'd be willing to spend accordingly, if they're a perennial contender over these next few years and looking to pay him what he's looking for, there's a very real chance you'll have him even beyond what his contract currently reads. Who knows if Holliday will even be enough, as Detroit might still want one more prospect added to the mix, and Baltimore shouldn't let that deter them from pushing this deal to the finish line. They're a championship-caliber lineup as it stands and not a player in their everyday lineup is over 30 years old, and even cutting two prospects out of the mix would still leave one of the league's better farm system. The Orioles can strike gold pouncing on Skubal and round out a roster capable of winning championships, and it's imperative that even at a steep price, they make this one work and add Skubal to the fold for at the least another 2.5 years.
Rarely can a potential trade address the needs of each team the way something revolving around a Tarik Skubal-Jackson Holliday deal could. The Tigers have something special and Skubal and the Orioles have the best prospect in baseball, but under the current circumstances, Skubal can do more for what Baltimore is hoping to accomplish and the same goes for Holliday in Detroit. Skubal pushes the Orioles over the top and into the potential World Series favorites, and they'd have him another 2.5 years with what I consider a decent shot at re-signing him. Holliday provides a massive boost to a Tigers rebuild that realistically isn't ending for at least another couple years, aligning perfectly with when Holliday should be ready to play at a high major league level. And right now, keeping Skubal around at best a .500 club runs the risk of setting the franchise way back down the line. These two teams have another week to figure this out, but this is as much of a win-win trade as I've seen in some time. The Orioles and Tigers need to make this one happen.