Mailbag: Time warp, prospects will break your heart, and Joey Gallo

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Happy new year! Our holiday hiatus is now over and we’re ready to start bringing you all content again. Hopefully, CBA negotiations will heat up sooner rather than later so we can return to hot stove news and later preview the 2022 season. For now, let’s ease back into things with our usual Monday post: the mailbag.

As always, send your mailbag questions to viewsfrom314 [at] gmail [dot] com, or alternatively, send them to us via Twitter. We answer our favorites every Monday. Here are this week’s questions and responses:

Alex asks: If you could add one of the following to the current Yankees on their contract that they signed at the time, who would you take: Bernie Williams in 1998 (7 years $87.5M), Derek Jeter in 2001 (10 years $189M), or Mariano Rivera in 2007 (3 years $45M)?

This is a pretty easy answer, no? It’s The Captain. The current Yankees need to improve at shortstop, and getting 10 years of a Hall of Famer at the position seems like a no brainer. That’s nothing against Bernie or Mo, who were excellent in their own regard. It’s just that they don’t stack up considering how much the Yankees got from Jeter over that decade.

Jeter signed his $189 million extension entering the 2001 season, in which he turned 27. He hit .310/.380/.445 (117 OPS+) over the life of the contract and accumulated 41.2 WAR per Baseball Reference (44.8 per FanGraphs, for what it’s worth). There were also two top three MVP race finishes during that period (2006 and 2009). Not to mention that Jeter played in 150 games in all of those seasons except 2003.

Bernie’s contract ran from 1999 through 2005, and though the Yankees could use a center fielder on the 2022 club, they’re aren’t in a dire situation like at shortstop. They have more than enough competent outfielders right now, even if it means one playing out of position. Williams hit .298/.386/.480 (126 OPS+) during this contract, but his performance was frontloaded. 2002 was his last great season offensively.

Lastly, Rivera’s three year deal covered 2008 through 2010. He was hilariously great: a 1.64 ERA (271 ERA+) in 197 innings along with just one run allowed in 22.1 postseason frames. As great as he was, it would be a poor decision to choose an elite closer for three years over a great shortstop for a decade.

Again, no slight against Williams and Rivera. It’s just that transporting prime Jeter into 2022 would solve a massive hole on the current roster.

David asks: If you had to put together a Yankee break your heart team (i.e. prospects who we all thought would be all stars or at least major contributors) but fizzled over the last 15 years by position, who would be on it.  (I start with a battery of Manny Banuelos and Jesus Montero; Greg Bird at first; Jorge Mateo at short; Eric Duncan at third).

This is a fun one, especially during a time without any hot stove. Here’s my list:

C: Jesús Montero

David suggested Montero and I’ll go along with it, though he was traded away quickly after his big league debut. Remember, Montero annihilated the ball in his first taste of the majors, hitting .328/.406/.590 (166 wRC+) in a 2011 September call-up. He was Baseball America’s third-best MLB prospect in 2011 too. But Montero didn’t break our hearts in the way prospects usually do. Rather, we’re left wondering who else the Yankees could have traded him for instead of Michael Pineda.

1B: Greg Bird

I promise I’ll have choices different from David soon. I think we were all enamored with Bird after he blasted 11 homers in 178 plate appearances as a 22 year old in 2015, no? That 137 wRC+ positioned him to take over first base from Mark Teixeira in a seamless transition. Alas, shoulder surgery effectively derailed his career. That sweet lefty swing just wasn’t meant to be.

2B: Rob Refsnyder

I lol’d a bit here, because Robby Ref was never really a big prospect by any stretch of the imagination. He was extremely popular with online Yankees fans though, myself included. Refsnyder raked throughout the minors and the Yankees were running out some bad options at the position after Robinson Canó departed. Plus, Ref’s 2015 cameo (130 wRC+ in 47 PA) was encouraging, but not enough to prevent the Yankees from acquiring Starlin Castro to play second base.

3B: Eric Duncan, Eric Jagielo

Two for the price of one. I actually didn’t think Duncan would qualify given David’s 15 year window, but he just sneaks in. ’06 was effectively Duncan’s last year as a legitimate prospect; he posted a 135 wRC+ as a 21 year-old that season. He also saw time in Triple-A in 2006, but struggled, and then simply couldn’t figure things out at the highest minor league rung in each of the next three seasons. He’s now the Marlins’ hitting coach.

Jagielo was the team’s top draft pick in 2013 — six picks before Aaron Judge — but injuries and lack of power development held him back. There was hope that Jagielo, a top collegiate bat, would pepper the short porch with his lefty power. He was traded away in the Aroldis Chapman deal with Cincinnati.

SS: uh, Cito Culver? Kyle Holder?

To be clear: these guys did not break anyone’s hearts even though they were (overdrafted) first round picks. I don’t think expectations were ever particularly high. There’s just no one else to actually pick here, unless I’m completely overlooking someone.

OF: José Tábata, Slade Heathcott, Mason Williams

Remember when Tábata was going to be the next Manny Ramírez? Fun times. He peaked at 27 on Baseball America’s top 100 prospects list after strong low level showings in 2006 and 2007. After that, he floundered in Double-A in 2008 before the Yankees dealt him to Pittsburgh for Damaso Marte and Xavier Nady. Tábata played a few years for the Pirates, but would never again be mistaken for Manny. He’s somehow still just 32 years old and played in the Atlantic League and Mexican League this year.

The Yankees drafted Heathcott in the first round of the 2009 draft. He appeared in BA’s top 100 once (2013). Injuries and alcoholism hindered his playing career, but he did have one True Yankee moment and now works as the Director of Operations for More Than Baseball, a minor leaguer advocacy group.

Williams was the Yankees’ top prospect entering 2013, per Baseball America, and 32nd MLB-wide. He never became anything more than 40-man outfield depth in New York, though. 2013 and 2014 were brutal seasons for him, sinking his prospect status, though he did play very well as a 23 year-old in 2015 between Double-A and Triple-A. Good enough for an appearance in 8 major league games with the Yankees, in fact. He wound up nothing more than an up-and-down guy from Scranton in the years after, though. Williams departed as a minor league free agent after 2017.

SP: Phil Hughes, Joba Chamberlain, Manny Bañuelos

Hughes carved out a pretty solid big league career, but considering his prospect hype, he was a heart breaker. He topped out as the league’s fourth-best prospect in 2007 and had that incredible start against the Rangers as a 20 year old that summer (6.1 no hit innings before the hamstring injury). Unfortunately, he never lived up to his billing as the next ace of the stuff. Still, he did have some very good seasons in The Bronx, including 2009 as a relief ace. He also turned in fine performances in the rotation in 2010 and 2012, though even in those seasons he was inconsistent.

Perhaps no prospect in my lifetime resulted in more consternation than Joba, though. The debates about how the organization handled him were passionate a decade or so ago. BA ranked him third in its top 100 in 2008 after his absurd debut in ’07 out of the bullpen, even with The Joba Rules in effect. There were some flashes of excellence after 2007, but things simply did not work out. He bounced around to Detroit, Kansas City, and Cleveland after his time in The Bronx ended.

ManBan ranked in BA’s top-100 back-to-back seasons (2011 and 2012), but he was never the same after Tommy John Surgery in 2012. He returned to action 2014 and was OK, but the Yankees were clearly ready to move. They dealt him to Atlanta that offseason for David Carpenter and Chasen Shreve.

I’ll throw some honorable mentions in here: Christian García and Alan Horne. Two guys with big time stuff who could never stay healthy. García eventually got a cup of coffee with the Nationals while Horne fizzled out before getting an opportunity anywhere.

RP: JB Cox, Jacob Lindgren

The Yanks nabbed Cox with its second round choice in 2005, who was the University of Texas’ closer. He dominated in 2005 (Tampa) and 2006 (Trenton), which gave him the Mariano Rivera Successor title at the time. However, numerous issues cost him any legitimate chance to be a successful major leaguer: a bar fight in December 2006 in which he broke his hand, elbow surgery in 2007, and a confrontation with his Double-A manager in 2010.

Lindgren was the Yanks’ top pick in 2014, albeit as a second round selection. After posting outrageously good strikeout numbers in the minors, he was up with the Yankees for seven games in 2015. Elbow injuries plagued him to the point of the Yankees non-tendering him after 2016.

Chris asks: There’s been a lot of talk about Joey Gallo’s short stint in pinstripes thus far from Yankees fans, but if he were currently on the open market he’d surely be a hot commodity and command a $100M+ contract, right?

Oh yes, Gallo would get $100 million without question if he was a free agent right now. He turned 28 last month and would be one of the younger free agents available, not to mention his elite power and prolific defense to boot. Yes, he strikes out a ton, but that’s not going to stop most teams from giving him nine figures.

The Javier Báez deal (6 years, $140 million), seems like a reasonable estimate for Gallo if he were a free agent today. Perhaps Gallo would fall a little short of that considering that he’s a corner outfielder compared to Báez being a shortstop, but both are similar in terms of propensity to whiff while also hitting for power. Gallo is the better all around offensive player because he takes walks (Báez rarely does), but both have struck out north of 30 percent over the last two seasons with isolated powers above .200.


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  1. JPL

    I know he doesn’t fit the 15 year criteria, but just the mention of heartbreaking prospects always makes me think of Brien Taylor.

  2. rjd

    clint frasier and blake rutherford for OF; Miguel Andujar 3b;

  3. Wire Fan

    I’m getting close to adding Deivi Garcia to the list. Fastball that played up and a plus, high spin curve. Then the Yankees old pitching regime pushed a slider on him and it became his most used secondary pitch.

    I wonder what he might have done in a different organization. Or if the slider centric pitching philosophy regime was cleaned out earlier. Before they could “fix” another pitcher. Would have been good to see what Matt Blake could have done in his early development years

  4. Yankees Cano

    Can we add Chance Adams to the prospect break your heart team?

  5. It’s amazing to me that Jesus Montero fizzled out in the majors. Look at those 2 dingers – his oppo power was unreal.

    • DZB

      Didn’t he get busted for PEDs? That could explain a lot about his prospect profile as fall

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