Thoughts on Sox D-Day

The good, the bad and how Boston positioned itself for the future.

Jon Lester racked up 110 wins for the Red Sox before being traded to Oakland.

The Fenway frenzy of the past few days, which culminated with four trades Thursday, came just as quickly as the season fell apart. Remember when they had a few series’ victories sandwiched around the All-Star break? Me neither.

You know those big roundup stories you see in every season preview, the one with the list of all the players lost and gained from each team during the offseason? Well, the Sox got rid of four guys who would’ve been in that season preview under “lost,” and in return they got two outfielders having bad years, one middle-of-the-rotation starter, one struggling 21-year-old prospect, a Top 75 draft pick and a little bit more. Aside from John Lackey, it’s all from trading guys who would’ve walked away from the Sox for nothing (aside from a Top 40 draft pick for Lester) in two months. You simply can’t complain about trades like that, and it’s why Sox fans can’t be too upset despite their favorite team trading away a homegrown ace who beat cancer, won two World Series rings and made three All-Star games. They’ve seen every homegrown guy leave, from Clemens to Nomar, and Vaughn to Ellsbury. Heck, even Dwight Evans played for Baltimore late in his career. It happens in pro sports today, and you take the best compensation you can get for the player. Let’s look at the outgoing players and the incoming ones from the past week, player by player and random thoughts from the trade deadline:


Jake Peavy, SP, 33 (free agent to be)

Felix Doubront, SP, 26 (arbitration eligible in 2015)

Jon Lester, SP, 30 (free agent to be, would get qualifying offer)

Jonny Gomes, OF, 33 (free agent to be)

John Lackey, SP, 35 (1 year left at $500,000 salary)

Corey Littrell, SP, 22 (yet to start six-year control clock)

Andrew Miller, RP, 29 (free agent to be)

Stephen Drew, SS, 31 (free agent to be)


Heath Hembree, RP, 25 (yet to start six-year control clock)

Edwin Escobar, SP, 22 (yet to start six-year control clock)

PTBNL from the Chicago Cubs

Yoenis Cespedes, OF, 28 (1 year left at $10M salary)

Joe Kelly, SP, 26 (arbitration eligible in 2016)

Allen Craig, OF/1B, 20 (signed for 3 years/$25.5M)

Eduardo Rodriguez, SP, 21 (yet to start six-year control clock)

Kelly Johnson, IF, 32 (free agent to be)

Top 75 pick from the Oakland A’s

– It’s obvious simply by looking at the list of incoming players that the Red Sox got younger (but not too young) during the trade deadline. None of the players they received who will be on the team next year are older than 30. But they gave up three 30+-year-old starting pitchers.

– It’s not unreasonable to think the Red Sox won’t have many free agents this offseason. Koji Uehara, Burke Badenhop and Kelly Johnson stand as the three right now, but Badenhop and Johnson could be dealt at the waiver trade deadline.

– I hope Giant Glass has someone on-call for the Lansdowne Street garage. Cespedes hits the ball as hard as any player—outside of Giancarlo Stanton—since Gary Sheffield. He’s a beast. And, while there’s been much hand-wringing over his low OBP, it’s in part due to his poor BABIP, which can be traced to his high FB percentage. If that was too much alphabet soup for you, let’s put simply: He’s not going to play as many games in Oakland (or Seattle for that matter) and he should see more of his fly balls become homers or doubles. Call it the Adrian Beltre Theory.

– Doubront looms as the biggest loss at the trade deadline. It’s easy to say he was in the bullpen and floundering, but this is a guy whose peripherals compared to Jon Lester’s last season (and let’s assume that same valued xFIP stat is what led the Sox front office to believe Lester was only worth 4/$70M), and who had a string of 16 starts under 3 earned runs during a stretch of 18 games last season. He had one bad relief appearance after getting yoked around by the team, and they jettisoned the next three years of team control for nothing? There has to be more to this than they’re letting on. He goes from being one of the biggest assets of the franchise to almost nothing in 12 months. This could really be the stinker of the trade deadline.

– The return for Miller was one of the best prospects traded during the deadline. While Rodriguez is having a tough season in Double-A, he’s only 21 and his peripherals are still impressive. It sets up an all-lefty generation of Rodriguez, Escobar, Brian Johnson and Henry Owens, who are all slightly younger than the all-righty generation of prospects (Allen Webster, Brandon Workman, Rubby De La Rosa, Matt Barnes and Anthony Ranaudo). Even if there’s only a 33 percent success rate, that’s still three starters.

– Craig is worth a gamble at a low price. The upside is his All- Star self, and the downside is his current self, who is useless. Craig’s inability to turn on pitches has been well-documented, and while wrist speed is the first thing to go with aging players, let’s not forget the case of Adam Lind, a similar-age player who was thought to be all washed-up (and someone the Sox might have to eat the contract of in John Farrell compensation talks). Lind is now tearing it up again for Toronto. It’s worth taking a risk on a guy for $8M a year. The Sox did it at a higher price for Shane Victorino in 2013, and it worked out.

– Speaking of Victorino, the absolute best-case scenario for the Sox would be to have Lester suffer a similar post-deadline fate as Victorino did after being traded to the Dodgers in 2012. He completely hit the skids that year and ruined any free-agent value he had. If Lester—sans the help of David Ross—does the same in Oakland, it would be nice. The only problem is Oakland is a pitchers’ park. A post-deadline skid would be far more likely if he were traded to the Orioles and had to pitch at Camden Yards.

– The compensation pick from the A’s is being overlooked in all this. It’s only about 35 spots lower than what the Sox would’ve gotten if Lester had walked as a free agent…plus they got 14 months (maybe 15 months?!) of Cespedes.

– Not that Kelly Johnson will help much this season, but I’ve always thought of him as the RFP in VORFP. He’s always been the 13th best player at any position in fantasy baseball. He’s always available on the waiver wire and always picked up a few times a year, and he’s useful in that role. He’s the ultimate Replacement Fantasy Player.

– While there’s been a little buzz about Lester coming back as a free agent, I just don’t see the Sox putting out the amount of money needed to get him as free agent. He’s getting something like 6 years, $150M after putting up the best season of his career. It might look good in 2015 or 2016, but don’t forget this is his best season. At age 30. It’s unlikely he’ll do this for too long.

– But while we’re at it, would Cespedes take that same 4 year, $70 million extension?

– You have to give props to the Red Sox front office for having the conviction to go all out and sell off the team’s free-agents-to-be. Look at teams like the Phillies or the Diamondbacks that sell off one or two pieces (or none if you’re the Phillies). What’s the point? Or on the flip side, look at the Pittsburgh Pirates, who have a Top 3 player in baseball and are unwilling to give up much of value at the trade deadline every year. The result is they never do much, and acquire over-the-hill veterans to surround Andrew McCutcheon. Ben Cherington and Co. had a plan and followed it. The Sox will be better of for it in 2015.

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