Scott Boras Holding Keys to MLB's Future and Nearly $1 Billion in Contracts

The road to winning Major League Baseball's 2019-20 offseason goes through Scott Boras.

Certainly, the sport's foremost agent always looms large in any given hot stove season. Boras' offseason dealings are almost always measured in hundreds of millions of dollars. To wit, the $330 million deal he negotiated for Bryce Harper last winter was just one part of a $458.2 million total haul.

But if all goes well, Boras could get nearly twice as much just for his best guys this winter.

The main beneficiary figures to be Gerrit Cole. The ace right-hander is probably going to win the American League Cy Young Award on the strength of the 2.50 ERA and 326 strikeouts he posted in the 2019 regular season. For good measure, he tacked on a 1.72 ERA and 47 strikeouts in a brilliant postseason run with the Houston Astros.

When the Astros lost the World Series in seven games to the Washington Nationals, Cole seemed just as ready for free agency as he was upset over the defeat. He did his post-Game 7 interview as an "affiliate of myself" and notably wearing a Boras Corporation hat:

Like everyone else, we have Cole ranked as the top free agent of the 2019-20 class. Projections for his contract elsewhere include seven years, $242 million at FanGraphs and eight years, $256 million at MLB Trade Rumors.

Which is to say there isn't much doubt that Boras will make Cole, 29, the richest pitcher in MLB history. David Price's seven-year, $217 million pact with the Boston Red Sox doesn't stand a chance of holding up.

Meanwhile, Boras also represents the second- and third-best free agents on the market: third baseman Anthony Rendon and ace righty Stephen Strasburg, both of whom are former Nationals heroes.

"I think we're about to make Scott richer than he already is," Rendon said during the World Series, according to Bob Nightengale of USA Today.

Rendon, 29, is fresh off going from an underrated star to a full-blown superstar with a superb regular season (1.010 OPS and 34 HR) and an equally superb postseason (1.003 OPS and 3 HR). He's now easily the best position player on the free-agent market.

Strasburg, 31, flew under the radar with a 3.32 ERA and 209 innings in the regular season, but the 2009 No. 1 pick and three-time All-Star made a legend of himself with a 1.98 ERA and 47-to-4 strikeout-to-walk ratio in October.

The aforementioned sites put Rendon's likely contract between $211 million and $235 million over seven years. Strasburg could land either a five- or six-year deal, but a $30 million average annual value either way would bring his guarantee to $150 million or $180 million.

In any case, the Cole-Rendon-Strasburg trio represents a chance for Boras to land three free-agent contracts worth at least $100 million in a single offseason. That would be a first for him, which isn't even to mention that a $600 million haul for these three guys alone would exceed even his biggest total offseason free-agent hauls.

Data courtesy of MLBTradeRumors.com

And the bucks won't stop there, for elsewhere in Boras' stable of free agents are left-handers Hyun-Jin Ryu and Dallas Keuchel, outfielder Nicholas Castellanos and third baseman Mike Moustakas.

Though Ryu's age (33 next March) and injury history are bound to scare some teams away, others will come running for his MLB-best 2.32 ERA. Keuchel is about to turn 32 in January in his own right, but he's nonetheless a Cy Young Award winner who boasts a 3.33 ERA since 2014.

For his part, Castellanos is an extra-base-hit machine who went off with a 1.002 OPS and 16 home runs in only 51 games with the Chicago Cubs down the stretch of 2019. Moustakas has limitations as a hitter, but he's been a steady power supplier since 2017 to the tune of 101 long balls.

To boot, none of these four players was subject to a qualifying offer this winter. That means none will be tied to draft-pick compensation, which will make it that much easier for Boras to secure multiyear deals for them. FanGraphs and MLBTR project such deals will be worth between $165 million and $171 million.

Altogether, Boras' seven best clients could be worth as much as $842 million. And by the time that money is spent, the established order in Major League Baseball could look very different.

Bob Levey/Getty Images

The top teams of 2019 were the Astros (107 wins), Los Angeles Dodgers (106), New York Yankees (103) and Minnesota Twins (101). Logically, they should now be looking to throw their weight around in free agency.

Yet as we've covered elsewhere, only the Twins are in an ideal position to do so. While they have plenty of space in their books, the Astros, Dodgers and Yankees are all staring down luxury-tax-related constraints.

Other big winners such as the Oakland Athletics (97) and Tampa Bay Rays (96) are notoriously cash-strapped contenders who will likely be bargain-bin shopping in free agency. 

Then there are the Red Sox, Cubs and St. Louis Cardinals. Each of them have indicated (see here, here and here) they'll be focused on cutting payroll over the winter.

The floor would therefore seem to be wide-open not only for the Twins, but also for the Nationals, Atlanta Braves, Philadelphia Phillies, Los Angeles Angels, Texas Rangers and San Francisco Giants to guide the fate of the free-agent market. If they were to sign most or even all of Boras' top guys, the competitive landscape of MLB would be in for a major shift in 2020 and beyond.

Looking a little more long-term, perhaps it's wishful thinking to wonder if The Winter of Scott Boras will quell fears that free agency, as an institution, is dead or dying. As it is, the MLB Players Association's newly launched investigation into possible collusion is only the latest sign that there will be a work stoppage before the current collective bargaining agreement expires in 2021.

Then again, perhaps not. The Nationals just won the World Series with the help of a whole bunch of hired guns. If Boras indeed follows that up with a historic free-agent bonanza, both MLB and the MLBPA might come to some common ground that free agency, though undeniably imperfect, isn't beyond saving.

Whatever the case, the 2019-20 offseason will at least be one that Boras and his seven major clients look back on with a palpable sense of fondness.

Stats courtesy of Baseball Reference.