The Yankees are rolling. Well, they’re rolling well enough to be in contention for the second wild card and have a chance to reach the postseason. The only problem is the standings for the second wild card are currently a mess with a handful of teams in position to earn the playoff berth. But with a big weekend against the Indians, the Yankees can get rid of one of the teams in the second wild card mix.

With the Yankees and Indians meeting for the second and last time this season, I did an email exchange with Jason Lukehart of Let’s Go Tribe to talk about the 2008 trade of CC Sabathia, what it’s been like to have Nick Swisher on the Indians and the emotional stress of having your team in the one-game playoff.

Keefe: CC Sabathia threw his last pitch of the 2014 season on May 10 and some believe it might have been the last pitch he ever throws given the unknown nature of his leg. After thinking he could continue to be a staple in the Yankees’ rotation for a few years and be maybe the last, or one of the last pitchers, to reach 300 wins, at 208 that now seems impossible.

Living in New York, I don’t know many Indians fans. Actually, now that I think of it, I don’t know any.  So I’m asking you as an Indians fan what it was like to watch Sabathia drafted and developed for seven-plus seasons in Cleveland before being forced to trade him to the Brewers in the summer of 2008?

Lukehart: The Indians are almost never in a position to add a top level starting pitcher through free agency or a trade, so if they’re going to have one, they’ve got to draft and develop him, or trade for him before he reaches the majors.

Sabathia was drafted in 1998, which was before I had any real awareness of the draft. It was the middle of 2000 when I first heard of him, when he was promoted to Double-A while still a teenager. He was on the Indians at the start of the 2001 season, and he went on to finish second in the AL Rookie of the Year voting that year. I remember finding it really cool that he was the first player born the same year as me to play for the Indians.

He took a big step forward in 2003, and made his first All-Star team that season, and because Bartolo Colon had been traded away, that was the year Sabathia first felt like the ace of the rotation. He wasn’t quite as good the next couple years though, but then in 2006 he was great, probably one of the five best pitchers in the American League. That was the year I started picking which games to go to based on whether or not Sabathia was pitching.

In 2007 he improved again, and suddenly he was maybe the best pitcher in baseball. The Indians were awesome that season, and after being spoiled by the 90s teams, five straight season of missing the playoffs felt like an eternity, so it was a delight to have the team playing so well, and Sabathia was front and center in that. The Indians had never had an MVP or Cy Young winner in the 20-plus years I’d been a fan, so having Sabathia win the Cy Young was a big deal to me. At the same time, it felt inevitable that 2008 would be his last year with the Indians, and when the team couldn’t recapture the magic from the year before, it was inevitable that he’d be traded. Bring a Tribe fan, you sort of get used to losing the team’s best players after a few years, but it’s still a bummer every time.

Keefe: When the Indians traded CC Sabathia to the Brewers they received Matt LaPorta, Zach Jackson, Rob Bryson and a player to be named later. That player to be named later ended up being Michael Brantley.

The centerpiece of that deal was LaPorta, who became a bust, but it’s Brantley, who has turned into a franchise player, showing consistent growth in production each season and now hitting .320/.378/.509 with 16 home runs and 72 RBIs as an All-Star outfielder.

What happened to LaPorta and how refreshing is it to see a young player like Brantley grow within the organization?

Lukehart: LaPorta was a bust. A lot of highly-rated prospects are busts. He wasn’t even the most highly-rated prospect the Indians have had in the last decade who didn’t pan out, so while of course I wish he’d turned into the slugging first baseman many predicted he would become, I never lost much sleep over it. I’ve liked Brantley for a while, and there’s real value in a slightly above average young player who can hold down a spot in the lineup for a few years. I certainly didn’t see a season like this one coming from him though. The Indians have a solid core of hitters, all fairly young and under team control for another three to six years, a group that includes Brantley, Carlos Santana, Yan Gomes, and Jason Kipnis.

Kipnis is having sort of a down year, possibly because of an oblique injury, but he was one of the best second baseman in baseball last year, and Santana has successfully transitioned from behind the plate to first base (after a short stint at third base, which didn’t go so well). Santana moved because Gomes is a great defensive catcher who also hits well, and now Brantley looks like maybe the best of the bunch. This core isn’t on the same level as the Belle/Lofton/Ramirez/Thome/Vizquel group from 20 years ago, but they’re good, and if the Indians can find a way to build a better starting rotation, the team should be competitive over the next few seasons.

Keefe: Nick Swisher might be my all-time least favorite Yankee, and that’s saying a lot because of Kevin Brown’s tenure with the team and Javier Vazquez’s and Raul Mondesi’s. But Swisher carried himself in a way that made Yankees fan dislike aside from him going 21-for-130 (.162) in four postseasons with the Yankees. Swisher was playing himself out of town long before his defensive lapse in Game 1 of the 2012 ALCS that lost the game for the Yankees in extra innings and caused Derek Jeter to break his ankle, and before his meltdown with the Bleacher Creatures in Game 2 of that same ALCS. I wanted Swisher out of town as fast as possible and I got my wish when the Indians signed him to a four-year, $56 million deal after the 2012 season.

The last time the Yankees and Indians met (July 7-9), Swisher entered the series hitting .197/.287/.317 with five home runs and 29 RBIs. But sure enough, he hit two home runs in the four games, including one off Masahiro Tanaka, to stick it to Yankees fans.

What are your thoughts on Swisher as an Indian now that he has been with the team for almost two years? And what are, or were, your thoughts on his contract?

Lukehart: Yankees fans may have the luxury of turning up their nose at good hitters, but for the last decade in Cleveland, we’ve had to take what we could get! Swisher posted four very good seasons at the plate in New York, hitting 23 home runs with an on-base percentage of .374 in the worst of those four seasons. He’d been healthy too. I didn’t expect him to be an MVP candidate or anything, but he certainly looked like an offensive upgrade for the Indians when they signed him, and the contract, while pricey for a team without the revenue streams teams like the Yankees and Red Sox have, was probably a bit below the market rate for a guy with Swisher’s numbers.

Whether it was going from a hitter’s park to a (slight) pitcher’s park, or suddenly being the biggest name in the lineup after years of being overshadowed by better known players, or just getting older (I think it was probably just getting older), thing have not worked out in Cleveland. A strong September gave him okay numbers in 2013, but he’s been one of the worst regular players in the league this year, which makes the remaining two seasons on his contract look pretty grim.

Keefe: In 2011, Justin Masterson looked like he was becoming the front-end starter the Indians hoped they had traded for from Boston in 2009 when he put together a 12-10 season with a 3.21 ERA. He regressed in 2012, but bounced back in 2013, going 14-10 with a 3.45 ERA, making the All-Star Team as well. But this season between bad pitching and injury, Masterson was a mess for the Indians (4-6, 5.63) and eventually was traded to the Cardinals for prospect James Ramsey, who tore up Double-A this season before getting moved to Triple-A.

What happened to Masterson and why was he never able to find consistency from year to year? Do you agree with the trade?

Lukehart: Masterson has said he injured his knee during his second start of the season, but that it didn’t keep him from pitching. I don’t know, I guess it just kept him from pitching well. In terms of his inconsistency from year to year, I don’t really know that there is an explanation. I think what makes the great one great is their ability to do it game after game, year after year. The minor leagues are littered with pitchers who could throw a great game here or there, and most starters who last at the MLB level have a particularly good year or two somewhere along the way. I think Masterson was a good pitcher, but not a great one, and that’s what you’d get if you took his overall numbers from his years with the Indians.

In terms of the trade, I was fine with it. Masterson is going to be a free agent at the end of the season, and after the two sides were unable to work out an extension this spring (despite Masterson reportedly being willing to sign for three years, $45 million… maybe the front office knew something we didn’t!), there wasn’t really any way he was going to come back in 2015, unless it was on a qualifying offer, and after his walk rate spike dramatically and he went on the DL for the first time, I don’t know that the front office was thrilled about the idea of making him a qualifying offer. I suspect his numbers will look better in St. Louis, in part because he’s probably bit healthier after a few weeks off, and in part because pitching in the National League is easier. I think the Indians did the right thing though, getting something for him while they could.

Keefe: I was the President of the No Second Wild Card Club the moment it became a possibility that Major League Baseball might institute a one-game playoff to decide a spot in the division series. My voice wasn’t heard as they went with the idea anyway and here we are in the third year of the playoff format where any team .500 or better is technically still in the race until the end of the season.

Now that the Yankees are no longer an annual lock to win the division or win what used to be the only wild card, I have started to come around on the second wild card because for them, especially this season, it might be their only way into the playoffs. I always said I don’t know if I could emotionally or physically handle a one-game playoff at the end of the season to get into the postseason, but this year I might find out.

You had to deal with the one-game playoff last year when your Indians played the Rays. What are your thoughts on the second wild card?

Lukehart: It’s funny how your favorite team’s circumstances can change your view on the second wild card, isn’t it? Last season I was happy about the second spot, because it seemed like it gave the Tribe a much better chance of reaching the postseason. Then they won their last 10 games of the regular season, and won the first wild card, and suddenly a bemoaning the existence of the second spot. “The Indians should be going straight to the ALDS!”

The wild card game’s merit will change year to year. In 2013, there were three teams all bunched together, and it made sense that they all still had a chance after 162 games. This year it looks like the Angels might be forced to play a do-or-doe game against a team with eight or nine fewer wins, which doesn’t seem so fair. I like that it places an increased value on winning the division, but I don’t like that it increases the chances that a team with a record barely above .500 might get into the playoffs.

As for the one-game nature of it, think of it as going straight to Game 7, which the Yankees have played their fair share of. If you can survive losing four straight to Boston in 2004, you can survive the wild-card game!

On Friday morning on YES, the July 1, 2004 game between the Yankees and Red Sox was playing on Yankees Classics (otherwise known as the Derek Jeter-goes-diving-into-the-stands game). That game happened just over 10 years ago and I can still remember where I was when watching it, having attended the Yankees’ win over the Red Sox the night before. But as the rivalry half-heartedly coasts through another season, it makes me realize how far removed we are from the battles of 2003 and 2004, and even 2005, 2006 and 2007. If I wasn’t going to be at Fenway Park this weekend, there’s no chance that 10 years from now in 2024 I would remember where I was for an August Yankees-Red Sox game.

With the Yankees still fighting for a playoff berth and the Red Sox trading off nearly their entire team and completey changing their roster for the second time in two years, I emailed Mike Hurley of CBS Boston because that’s what I do when the Yankees and Red Sox play each other.

Keefe: Nine months ago the Red Sox completed the most improbable season in major sports history by winning a World Series they had no business winning. The real Impossible Dream season of 2013 was sandwiched between a 93-loss 2012 season and what might be another 93-loss season in 2014.

Aside from Jacoby Ellsbury signing with the Yankees and Jarrod Saltalamacchia signing with the Marlins (but who cares?) the Red Sox returned basically the same team, position-player wise in 2014 and the same rotation. But since last week the Red Sox have now traded Jake Peavy, Felix Doubront, Jon Lester, Jonny Gomes and John Lackey. All three pitchers responsible for the four wins in the World Series are gone.

Is this August 2012 all over again? Are the Red Sox going to hit a 16-team NFL parlay in 2015 and win the World Series again?

Hurley: Wow, a presumptuous Neil Keefe just fires off an email on trade deadline day and expects me to have the time to respond. So bold. So typically Neil.

The answer to your question is yes, obviously the Red Sox are going to win the World Series in 2015 behind Yoenis Cespedes and Joe Kelly. Don’t worry about the starting rotation — starting pitchers aren’t important! That’s the Red Sox’ new philosophy, I guess. Either that, or they really like their pitching prospects. We’ll see at least one of them this weekend against New York.

Keefe: To be honest, I didn’t think you would answer. I thought you would be too upset about the Red Sox trading off every player on their team including their 30-year-old, left-handed ace and franchise staple. Then I remembered that you don’t care about the Red Sox the way you used to and that’s because of the ownership group.

Sure, you make jokes from time to time about my love for Derek Jeter, but like we have talked about countless times, he has been the shortstop of the Yankees for basically our entire we-can-understand-baseball lives. The Red Sox don’t have that player. They haven’t had that player in a long, long time. For any Red Sox fan that’s a child to about mid-to-late 30s, they haven’t had that player. Roger Clemens left. Mo Vaughn left. Nomar was traded. The closest thing I guess would be David Ortiz, who started his career with the Twins, but Jon Lester had a chance to be that guy.

I don’t get why Lester and the Red Sox couldn’t come to an agreement and I’m guessing that it had to do with the team and not the player. The Red Sox were adamant about not wanting to pay pitchers who were 30-plus years of age, but when it came to their ace and a two-time World Series champion, you would think they would have made an exception. The Red Sox have a bajillion dollars and could have afforded to blow some money on a guy that helped bring them two titles in seven years. But money is also why they didn’t do because they know that even Lester were to be traded (which he was) and signs elsewhere in the winter, they are still going make money. People in Boston aren’t going to stop going to Red Sox games and buying merchandise and singing “Sweet Caroline” whether Lester is on the team or not. This ownership group has taken so many negative PR hits over the years and shrugged them off only to make more and more money and sell more and more Fenway Park bricks that they must have thought, “What’s another bad story about us?”

Please tell me you still have a soul and are upset that Lester isn’t going to be a lifetime Red Sox. Please don’t tell me some BS about how it’s a business and they got a good return for him.

Hurley: Well I think you’re wrong to say that Red Sox fans are going to keep filling Fenway Park and keep spending money by the buckets. It’s true that Fenway is still jammed full of idiots screaming “SWEET CAROLINE!!!” in the middle of the eighth inning when the Sox are getting trounced by a sorry-ass team like the Cubs. Yes, that happens. But what’s happened over the past few years is that the Red Sox are getting less and less cool.

You’re aware that I turned 21 in 2007, so I obviously started going to bars on a regular basis that year. You’ll also recall that the Red Sox won the World Series that year. The Red Sox were on top of the world. Everywhere you looked, the Red Sox were there — on hats, shirts, TVs, tattoos, everything. They owned the region.

From 2007-2011, you could not find one television in a bar NOT tuned to the Red Sox in the Boston area.

But in the past few years, I’ve been in a lot of bars and restaurants during Red Sox games, and the TV hasn’t been showing the game. It’s been showing random things — nothing, really — and nobody in the bar seems to care. This may seem like a small thing, but I think it’s pretty indicative of the Red Sox’ current state in the area. They’re just not hot anymore.

And, as you point out, they’re shipping away a guy who grew up with the organization, won two World Series, beat cancer and has simply been the man for the past nine years. All because they’re afraid he won’t be spectacular for six years? It’s pretty weak.

I understood why they let Ellsbury walk for big money last winter, and I understand the business decision to not take the risk on Lester. At the same time, if you don’t extend yourself for Lester, who on earth do you extend yourself for?

(Unless the Red Sox have a secret plan to sign him in the offseason, no matter what. If so, that would be nuts and hilarious and awesome.)

Keefe: I don’t think Jon Lester is going to sign back with the Red Sox as much as some delusional Red Sox fans do. The whole point of him extending his contract for a “hometown discount” would have been that he would remain a Red Sox for life. Now that he is with Oakland, the lifetime Red Sox part of the equation is gone and with him being an impending free agent, he is going to chase the money. Some team is going to offer him seven years (Hello, Yankees!) and when Jon Lester sees some $150-plus million deal starting him in the face he is going to take it. Let’s not forget that Lester is finishing up a five-year, $30 million deal and from 2009 through this season it’s taken him the same amount of time to earn nearly what CC Sabathia is this season to pitch horribly and then not pitch at all.

The best-case scenario for the Yankees was that Lester would end up with a team that has no intention of extending or re-signing him and that’s what happened. Instead of landing with the Dodgers or Cardinals, he’s in Oakland. So I want to thank the Red Sox for trading him there and not to a big-market team where he might have stayed.

You should come down to New York next season for his first start in the Bronx.

Hurley: I might do that. I like Jon Lester. That’s really rare for a baseball player, I feel. They’re all self-absorbed, rich-out-of-their-minds awful people, for the most part. Lester is a decent guy, the kind of person that makes you wonder what the hell he spends all that money on. I don’t see Lester cruising in a Ferrari during the offseasons, you know?

Any way, I’m glad you didn’t really ask me anything in that email, because I have an important topic I need to bring up here.

The New York Yankees. Big team, lots of fans, right? Lots of people care about the Yanks, safe to say? Large following? People want to see them win and everything? OK.

Then how in God’s name is everybody OK with having the Ghost of Derek Jeter play shortstop down the stretch while putting Stephen Drew at second base, a position that a trained monkey can play?

Derek Jeter is not as awful at shortstop as everyone in America likes to make him out to be, but he is still most definitely bad at it. He’s old, and he’s just gotten worse and worse at the position for the past seven years. Yet because he’s JEETS, and because of Re2pect, the Yankees are going to waste literally the only useful thing Stephen Drew can do on a baseball field? That’s insane.

You’re going to have a second baseman who hits .170. That’s solid. There weren’t any big-name second basemen on the free-agent market last winter, were there?

Keefe: I kind of sort of remember there being a big-name second baseman being available last winter. What was his name? Brian Roberts? Kelly Johnson? Ah, I forget it. It will come to me though.

The Yankees should have signed Robinson Cano for 10 years and $240 million. Who cares? I don’t. It’s not my money. Anyone who doesn’t have ownership in the Yankees shouldn’t care either. The Yankees are in the mix for the AL East despite having 80 percent of their Opening Day rotation on the disabled list and a middle of the order that is a disaster. WAR or math or science might suggest that even with Cano the Yankees wouldn’t be leading the division, but I know they would. Roberts and Johnson left every person on the base imaginable and played a collective horrible defense costing the Yankees several games. They should have signed Cano and worried about him sucking at the end of his deal later on. Instead we have Jacoby Ellsbury, who needs days off here and there and has given new meaning to the word “streaky” and Carlos Beltran, who might be softer than Mark Teixeira.

Derek Jeter should be playing shortstop over Drew because he’s Derek Jeter and I don’t care if mid-90s Omar Vizquel walks through the door, Derek Jeter is playing shortstop. Have some effing RE2PECT would you, Michael?

The Drews are like the Weavers to me in that I picture their family driving around in a station wagon yelling, “WHO RULES? DREW RULES! WHO RULES? DREW RULES! DREW RULES! DREW RULES!” like the O’Doyles in Billy Madison.

I’m not happy the Yankees got Drew and that they might re-sign him and he could be playing shortstop next season, but things could be worse. They could have traded for John Lackey.

Hurley: I legitimately laughed out loud at the DREW RULES scenario. It’s very likely the case.

I just feel like there is RE2PECT, and then there is stupid. And if you really RE2PECT Derek Jeter and want to send him out a champion, you should field the best team possible. That means Jeter gets penciled into the lineup with the letters “D” and “H” next to his name every night. To do otherwise is pretty delusional, to borrow a term from you.

I looked it up for you — Brian Roberts hit .242 with RISP. Johnson hit .280.

Do you know what Drew has hit with RISP? He’s hit .154, Neil. One-fifty-four. He also hit .111 last year in 16 playoff games.

So hey, enjoy Stephen Drew. I’m sure he’s going to be awesome.

Keefe: Well then it must have been my imagination that Brian Roberts and Kelly Johnson were as bad as they were, but I know they were. But thanks for sharing Drew’s average with RISP for me to make me feel even better about the Yankees’ trade deadline moves.

One of the biggest takeaways from deadline day was how ecstatic Red Sox fans were about Yoenis Cespedes coming to Boston. Unless I missed the news that Major League Baseball will no longer decide the season based on 162 actual games and will use Home Run Derby to determine the champion, I’m not sure failing to re-sign your 30-year-old left-handed ace and trading him for a .250 hitter who strikes out a lot, but can hit mammoth home runs is the best move, but hey, starting pitching in baseball isn’t that big of a deal. I also find it odd how many people were instantly fine with Lester being traded for a bat, considering what Lester meant to the team and the fact that Cespedes will be a free agent after 2015.

Yoenis Cespedes woke up on Thursday morning on the best team in Major League Baseball. Now he is on the worst team in the AL East with nothing to play for over the next two months.

Good times never seemed so good!

Hurley: Yeah, I mean, I think the initial excitement was based on the fact that:

A) Everyone knew Lester was getting traded, and
B) Everyone expected the Red Sox to simply receive a package of prospects in return.

To see the Sox get an established big league hitter who can mash, it provides some excitement. I don’t think anyone thought, “Holy crap, we got Cespedes! Next stop – championship!” I think it was more, “Holy hell, the Red Sox actually got someone I’ve heard of! And he doesn’t suck!”

Cespedes has more home runs this season than all Red Sox outfielders combined. (Even more if you factor in HR Derby dingers, like Jayson Stark did yesterday!) He provides the Red Sox with something they desperately need. If it works out this year, he’s someone they can sign long term to hit bombs. Or maybe they can move him down to Miami, where he’ll be the biggest star in the history of Miami, for Giancarlo Stanton, or something wild like that. You never know. There’s reason to be excited for Cespedes, even though none of it has to do with being competitive at all this year.

Me personally, I was pissed off that they got Cespedes. There I was, ready to see everyone traded away and ready to see tickets for the next two months become cheaper than dirt. (I bought tickets in April for $3. THREE DOLLARS!) I was so ready for a summer like 2012 again, where the stands are filled almost entirely with just baseball fans and not yahoos who think going to the ballgame is cool. Alas, adding Cespedes should keep people interested for a few extra weeks, and I might not get my cheap seats until mid-September. These are the things I care about.