OTM Roundtable: Redoing a transaction

We’re keeping with the “What If?” theme of the week at SB Nation for this edition of our staff roundtable. Everyone has a transaction or two or three or a billion that they would re-do. All of us, after all, would be the best GM of all time if just given the chance. So, that’s the question this week. Which transaction in team history would you re-do if given the opportunity? That could mean reversing a transaction or it could mean pulling the trigger on a trade or signing that was rumored as a possibility but never came to fruition. The only limitation I put on this one was that the Mookie trade was not an option. We’ve talked enough about that for now.

Jake Kostik

Even if the Mookie trade were an option, I wouldn’t reverse that deal because I think it was 100 percent the right move. Betts had no interest in signing an extension, and with him in theory going into free agency regardless of what happens, we have as much a chance of being the high bidders for him in the offseason now as we did before.

Instead, I think I would change a draft pick. A lot of the deals have happened the exact same way as I had personally hoped (although the Sale extension is looking iffy right now) and I’m not really looking to change any deals that would have negatively impacted our chances of winning in 2004, 2007, 2013, and 2018, even if it means we may have won in 2012 or 2005.

The pick I’m choosing to reverse is the seventh overall of the 2013 MLB Draft: Trey Ball. As many will remember, I have long been angry with the pick of Ball, a player I never felt was worthy of a top seventh pick, and that I was a huge fan of two rival outfielders, Clint Frazier, and Austin Meadows. Well, one of those players was available at our pick, and we chose... uh, Ball.

Look, I’m no draft master. I don’t have all the answers. My shadow drafts have yet to turn out great in the last two times I’ve done them since transitioning to being a writer. But it was clear even then the talent that Meadows had, and I felt he was a top 3 talent that somehow fell into our laps. And we passed. And it made me forever angry. Now he’s on the Rays. Whoops.

Keaton DeRocher

Hindsight is, of course, 20/20, and you can do this with almost every draft but with my transaction that I would change, it’s the Jay Groome pick in the 2016 draft. Groome came into draft with some red flags and dropped tot he Red Sox at the 12th pick because of them after being graded one of the top pitchers in the class. I get the appeal at the time thinking you’re getting “value” but just to name a few of the other players picked after Groome at 12 there was Gavin Lux at number 20, who is currently the #2 prospect in all of baseball and major league ready at a position (second base) the Red Sox really need help with now and long term. Carter Keiboom at number 28 who is another MLB ready middle infield top prospect. Will Smith at number 32 who is a catching top prospect and who had an impressive debut for the Dodgers last season. It’s easy now to look at this and say the Red Sox biffed this pick compared to at the time they actually made it, but hey that was the prompt so I’m riding with it.

Jake Devereaux

For me this one is a no-brainer—Jon Lester. The Red Sox royally screwed up on this one and have even admitted it in recent years. Lester was, and remains to this day, an absolutely dominant postseason pitcher, a workhorse lefty, and a potential Hall of Famer. If the Red Sox had brought him back the real loser would’ve been the Cubs who very likely would not have won the 2016 World Series, the Red Sox also would have avoided signing David Price. Avoiding signing Price might’ve been worth the price of admission for me. I really don’t like him. It also would’ve saved the media and Price a whole bunch of anguish. Frankly, Lester has been far better than Price as well. Since they both signed new contracts in Price in 2016 and Lester in 2015, Price has thrown 588 IP with a 3.84 ERA and 1.20 WHIP, Lester has thrown 941.2 IP with a 3.54 and 1.24 WHIP. From 2016 forward Lester has been worth more fWAR as well. Lester says he may even be open to finishing his career in Boston. If I were in charge I’d welcome back the greatest home grown pitcher of the last 30 years with open arms.

Phil Neuffer

It was before my time, but I always wonder why the Red Sox let go of Carlton Fisk. He was one of the best catchers ever and when he signed with the White Sox before the 1981 season he was still in his prime, albeit on the back end. He was worth 3.8 fWAR and had a 118 wRC+ in 1980 and it’s not like he declined demonstrably in the ensuing years in Chicago. He made four more All-Star teams, finished third in MVP voting in 1983 and had six more seasons of at least 3.0 fWAR. Fisk chose to go into the Hall of Fame with a Red Sox hat on, so he clearly had affection for the organization. It makes you wonder what might have been, and although I would have only been alive to see the twilight of his career, I would have liked if Fisk only wore Red Sox.

If you’d like a more recent addition and one for which I was very much alive, I would reverse the Pablo Sandoval signing. I wanted Sandoval to be great for the Red Sox, but even when his deal went through, it gave me a bad feeling. Although he had produced 3.2 fWAR the year before in San Francisco, the contract the Red Sox offered in 2014 seemed a little expensive for someone whose OPS+ and wRC+ had declined in three-straight seasons. In many ways, it seemed like the Red Sox were going for the brand name when generic would have been just fine. Unfortunately, that bad feeling I had wasn’t just pessimism. Sandoval logged -1.6 bWAR across parts of three seasons with Boston and was cut midway through the 2017 season despite being owed $17.6 million that year. There’s no way to know if the Red Sox would have spent that money better if Sandoval signed somewhere else, but there’s no way they could have spent it worse.

Shelly Verougstraete

I’m not sure what the Red Sox have had against young first baseman. I wrote this week about the Anthony Rizzo deal but there was another swap even worse, Larry Anderson for Jeff Bagwell. Anderson threw 22 innings in his 15 relief appearances with a a 1.23 ERA. He strugged in the ALCS posting a 6.00 ERA in 3 innings and then left for San Diego after the season ended. Bagwell went on to win the Rookie of the Year in 1991, MVP in 1994 and Hall of Fame in 2017. Unbelievable.

Michael Walsh

This may seem like an obvious choice, but the Pablo Sandoval deal will always be my choice as the one of the Red Sox’ biggest contract disasters. Not only was he ineffective after signing a 5-year $95 million deal, but he was a constant distraction in the offseason. After every poor/injury-riddled season he would have, there would be rumors and pictures floating around about his “new” offseason training program that shed him a few pounds and got him in shape. Every time, however, he proved to be just as ineffective as the years before. Although his contract is now (finally) up, Pablo Sandoval will always be notorious as a bust around Boston.

Mike Carlucci

Let’s trade for Todd Helton! Well, not now. In 2007. Back then there were four players being discussed for the Rockies first base legend: Mike Lowell, Julian Taveraz, Manny Delcarman, and Craig Hansen. The hangup? The two pitching prospects. Hansen, who started his Red Sox career in 2005 fresh out of the draft with inning after scoreless inning...kinda flamed out. Manny Delcarmen was great for two seasons - 2007 and 2008 - and then fell apart. So we would have lost those. Mike Lowell was a fan favorite but probably a wash with Helton. Tavarez? Roll the dice on someone else and see how it goes.

Maybe Anthony Rizzo isn’t traded for Adrian Gonzalez. Maybe Adrian Beltre is extended. Maybe Carl Crawford is avoided because of another Big Name(TM) on the roster.

Was this the back half of a near Hall of Fame career? Yes. Would Helton lose something from his .287/.385/.442 line without any games in Coors? Certainly. Would this have ended up being a terrible deal? Probably not.

Brady Childs

Matt says I can’t complain about the Mookie trade, so I’m going to complain about another stupid, financially motivated trade where a future hall of famer was dealt for pennies on the dollar: Tris Speaker!

Speaker was dealt at the peak of his powers due to a small financial dispute between Speaker and the owner, Joe Lannin. Terry Pluto of Cleveland.com wrote a terrific article detailing this, but the long and short of it was that Lannin wanted to cut his salary from $14,000 to $9,000. Speaker was right to call him out. He had recently placed in MVP voting for four straight years and had won three years prior. Along with that, he was the best hitter on a team that had just won the World Series! Time truly is a flat circle.

Speaker was traded to the Cleveland Indians where he led all of baseball in batting average, on-base percentage, and slugging percentage. It would take five more seasons, but Speaker would win a championship in Cleveland in 1920. The Sox didn’t miss a beat, winning championships in 1916 and 1918 before spitting in the game’s face again by trading The Babe. That deal greatly overshadows this deal, but the root cause of both deals was the same: greed.

Bryan Joiner

I’m gonna cheat again. I don’t want the Red Sox to have had Alex Rodriguez. Things turned out way too well without him, and now that he spent the majority of his life on the Yankees, he seems very much like a Yankee. I can’t imagine wondering what would have happened if the union allowed the trade(s) to go through, ones which would have brought A-Rod and Magglio Ordonez to the Red Sox for, if memory serves, Manny Ramirez and Nomar Garciaparra. It’s so seismic that it’s generally not best to think about, like the Joe DiMaggio/Ted Williams trade that was consummated over drinks and undone in the morning, but for this exercise, it works. If I would change this simply because I could, it’s because I’m team chaos, and, well, who isn’t right now?

Matt Collins

The real answer to this question is one that I was absolutely floored no one claimed to write a larger piece on, and I’m even more shocked no one even really mentioned it here. I’m not going to either, though, because I’m going to do a longer post of my own over the weekend. So, I’ll go in a different direction than everyone else and not focus on the players. Instead, I’m going with hiring Bobby Valentine. Instead, the Red Sox could have hired literally anyone else and I would’ve been good with it. I feel like I don’t really have to explain myself here, right?