If The Boss Were Still Alive

Toward the end of February, the Boston Red Sox signed 19-old-Cuban prospect Yoan Mondaca for $31.5 million. Under baseball's borderline-incomprehensible international signing rules, that amount was doubled to $63 million, half to Moncada, and half to Major League Baseball as a "tax" for exceeding Boston's international spending limit. 

Moncada is a highly-regarded prospect, projected to play second or third base, possibly shortstop, with speed and the potential to hit for average and for power. He doesn't seem to fit in with the Red Sox, who have second baseman Dustin Pedroia signed through 2021, newly-signed Pablo Sandoval under contract through 2019 (with a 2020 option), and 22-year old shortstop Xander Bogaerts under team control through 2019. But Moncada's expected to need a year or two in the minors, and a lot can change over two seasons.

The surprise isn't that Moncada got $31.5 million (and that's just a signing bonus; he'll earn a salary above and beyond that) nor that the big-budget Red Sox got him. But a lot of people figured he'd wind up a Yankee. The Yankees, after all, are the richest franchise in baseball, and they enter 2015 with a 31-year-old second baseman who's played the position only 34 games in the majors and batted .220 over the past three seasons, along with a shortstop platoon consisting of a left-handed batter with a .243 career average and a right-handed batter with a .234 career average. Reportedly, they bid $25 million ($50 million with the penalty), with general manager Brian Cashman wanting to go higher but principal owner Hal Steinbrenner balked.

That scenario led, predictably, into many Yankee fans and pundits moaning that if Hal's father, George Steinbrenner, aka The Boss, were still alive, the Yankees would've signed Moncada. Certainly, the elder Steinbrenner had a reputation for not being outbid for free agent talent that could help the Yankees. Of course, his sons, Hal and Hank, haven't exactly been tightwads, as they committed nearly half a billion dollars last winter, signing outfielder Jacoby Ellsbury (seven years for $153 million or, optionally, eight for $169 million), catcher Brian McCann (five years for $85 million or six for $100 million), pitcher Masahiro Tanaka (seven years for $155 million with a player opt-out after four years for $88 million), and outfielder Carlos Beltran (three year, $45 million). Still, there's little question that Moncada would be a good fit for the Yankees, nor that the $13 million by which the Red Sox outbid them isn't that large.

I'm still not convinced, though, that George Steinbrenner would've signed him. No question, the man excelled at signing free agents. He also didn't lose key players to free agency, an key reason for the Yankees' success that often gets overlooked. But he wasn't a big fan of young prospects. Moncada's 19, has never played in anything comparable to American baseball leagues, and, as noted above, is probably two years removed from the majors. That's not the type of player the late Steinbrenner coveted. 

Take the first Yankees world championship team under Steinbrenner, the 1977 team. (That's the year Reggie Jackson hit three home runs in the last game of the World Series.) Left fielder Roy White, catcher Thurman Munson, and pitcher Ron Guidry were drafted by the Yankees. Jackson and pitcher Catfish Hunter were signed as free agents. Every other starting position player, every other member of the five-man pitching rotation, the closer and the key setup man--they were all acquired via trade. Some of them were astute deals involving veterans, but many involved prospects. Steinbrenner traded a lot of prospects for established players, filling other needs via free agency.

Want more proof? Look at the greatest Yankee team of recent vintage, the 114-48 1998 squad that swept to a World Championship. Outside of the Core Four of shortstop Derek Jeter, catcher Jorge Posada, starter Andy Pettitte and reliever Mariano Rivera, the team was assembled by trade (first baseman Tino Martinez, second baseman Chuck Knoblauch, third baseman Scott Brosius, left fielder Chad Curtis, right fielder Paul O'Neill) mostly for prospects, and free agency (DHs Darryl Strawberry and Tim Raines; starters David Wells, David Cone, Hideki Irabu and Orlando Hernandez; reliever Mike Stanton). The only home-grown regular, outside of the Core Four, was center fielder Bernie Williams.

Wait, you're saying, that "outside of the Core Four" line is pretty glib. True enough: The Yankees drafted Posada and Pettitte and signed Rivera as an amateur free agent in 1990. They drafted Jeter in 1992. The Boss didn't trade any of them away, so why do I think he had a thing against prospects?

Because he didn't have a chance to trade them away. Steinbrenner was suspended from the Yankees in 1990 for his dealings with outfielder Dave Winfield and reinstated in 1993. During his absence, the Core Four rose through the Yankees farm system; all four arrived in the majors in 1995. And even then, Steinbrenner wanted to trade Rivera for a shortstop who would have blocked Jeter. The man saw prospects more as a means to end, rather than an end.

So would George have spent mid-eight figures for a 19-year-old? It's possible, but I question it. Maybe he'd have more aggressively pursued pitchers Jon Lester, Max Scherzer, or James Shields this winter. I think he wouldn't have let second baseman Robinson Cano depart a year ago, creating a hole that Moncada might have been able to fill. (As I said, I think the Yankees' ability to retain its key players is an underappreciated Steinbrenner strength.) But I think there's a decent chance that Yoan Moncada would be a Red Sox farmhand even if The Boss were still alive.

Derek Jeter and Workplace Etiquette

The encomiums will be endless, and this isn't one of them. Rather, it's a cool story that Joe Sheehan threw out as an aside in his newsletter (which is fabulous and a subscription I recommend highly - you can get it here).

In 1994, the Yankees had the best record in the AL when the strike ended the season. In 1995, they were second to Boston but were the wild card team, losing to the Mariners. So hopes were high heading into 1996. But their switch-hitting shortstop, Tony Fernandez, broke his elbow in spring training. Management wanted 22-year-old rookie Derek Jeter, who had hit .306 with a .383 on base percentage in four minor league seasons, to play short. Principal owner George Steinbrenner, though, was unimpressed with Jeter during 15 games in New York in 1995, as he hit just .250 with a .294 on base percentage, striking out in over 21% of his plate appearances. Steinbrenner had his eyes on Mariners shortstop Felix Fermin, a slick fielder who had batted .317 in 1994 but had lost his job in 1995 to two future Yankees: Luis Sojo and rookie Alex Rodriguez. To get Fermin, Steinbrenner wanted to trade a 26-year-old Panamanian pitcher who'd struggled to a 5.51 ERA in his rookie season (a lot of rookies in this story), throwing 67 innings split between starting and relieving. The pitcher: Mariano Rivera. 

So to review: Steinbrenner wanted to trade Mariano Rivera for a shortstop coming off a .195 batting average in order to avoid playing Derek Jeter.

The moral of the story, of course, is that sometimes it's OK to talk your boss out of doing something really stupid.