Red Sox

Mookie Betts and the Red Sox have four options to weigh this winter

Mookie Betts and the Red Sox have four options to weigh this winter

The Red Sox must determine how to proceed with Mookie Betts this winter, and fast.

If they're going to keep the former MVP, the sooner they know it the better, because fitting his $30 million into a $208 payroll will not only take some serious creativity, it will leave them rifling through clearance racks to fill the rest of the roster.

We are all aware of their four possible paths: trade Betts now, trade him by July 31, let him play out the season and become a free agent, or sign him to an extension.

Some of those possibilities feel more likely than others, which is why we're here to apply some odds.

1. Trade him now: 55 percent

This still feels like the most probable course of action, given Betts' off-stated desire to reach free agency and the franchise's equivalent determination to get something for him before he leaves. Better to rip off that Band-Aid now, even if it means losing a little leg hair in the process.

Any team acquiring Betts needs to be able to fit his salary into its payroll, and that's more easily accomplished earlier in the offseason, especially since there's little chance the Red Sox contribute anything towards his salary. The optics of trading Betts are bad enough — paying someone else to take him would be inexcusable.

2. Trade him in July: 15 percent

There's some appeal to this approach, which gives the Red Sox a chance to make one final run with their Gold Glove- and Silver Slugger-winning right fielder, especially if the offers this winter prove underwhelming.

But there's one obvious flaw — what if July 31 arrives and the Red Sox find themselves in contention? At last year's trade deadline, for instance, a staggering 11 National League teams owned between 50 and 57 wins. Six of them could make legitimate cases for the wild card.

Good luck justifying a trade of your best player in that scenario, even if it's the right long-term move. Better to deal him now before putting new boss Chaim Bloom in that no-win situation.

3. Let him play out season: 20 percent

Former GM Theo Epstein used to bristle at the concept of trading a player before he could "walk away for nothing" by noting that a final season of All-Star production carries considerable value.

If the Red Sox can figure out how to absorb Betts' 2020 salary — perhaps by finding a taker for David Price and the $96 million remaining on his deal — there are worse problems to have than a lineup built around Betts, Rafael Devers, Xander Bogaerts, and J.D. Martinez.

If Chris Sale is healthy, that's a team that could win it all and then let whatever happens happen with Betts.

4. Extend him: 10 percent

It's sad that this feels like the least likely outcome, but we're just keeping it real.

There are two impediments to a long-term extension. One is Betts's aforementioned desire to hit the market and see what he's worth. The other is the very legitimate queasiness ownership might feel about extending anyone for more than 10 years.

That said, if Betts came to them with a reasonable number — say, 12 years and $340 million, slotting him between Bryce Harper and Mike Trout — there'd definitely be some in ownership pushing to get his signature to lock in the franchise cornerstone.

It doesn't feel like it's going to come to that, though, unless Betts experiences a change of heart about reaching free agency.

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Travis Shaw says return to Boston Red Sox 'makes sense on paper'

Travis Shaw says return to Boston Red Sox 'makes sense on paper'

After being non-tendered by the Milwaukee Brewers, could a return to the Boston Red Sox be in order for Travis Shaw?

With Mitch Moreland hitting free agency, the Red Sox should be in the market for a left-handed-hitting first baseman. That makes Shaw an obvious fit, and the 29-year-old agrees a reunion with Boston would make sense.

Shaw discussed the situation with Rob Bradford on WEEI's Bradfo Sho podcast

"I got non-tendered this week. It was kind of a hard decision. The Brewers did offer me but I decided I kind of wanted a fresh start and was willing to risk to see what was out there free agent-wise," Shaw told Bradford. "Just wanted a fresh start after everything that happened last year. Like you said, [signing with the Red Sox] makes sense on paper now we’ll see with who else call or what other teams call. That’s kind of what we’re sorting through now. We’ve had quite a bit of interest so far over this week which is an encouraging sign for me. We’ll just go from there."

Before the 2017 season, the Red Sox traded Shaw to the Brewers in the deal that brought reliever Tyler Thornburg to Boston. In his first two years with Milwaukee, Shaw was an integral part of the offense with 30+ home runs and an OPS well above .800. Last season, however, Shaw missed some time with a wrist injury and saw his production dip significantly.

Assuming Shaw can return to the type of player we saw in '17 and '18, he makes for an intriguing option for Boston in free agency. Along with his potential at the plate, Shaw brings versatility to the table as he can adequately play multiple positions.

Right-handed sluggers Michael Chavis and Bobby Dalbec currently are the Red Sox' options at first base. Chavis was solid in his 2019 rookie campaign, and Dalbec enters 2020 as one of the organization's top prospects.

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MLB rumors: Winter meetings preview - Five Red Sox moves to watch as offseason begins in earnest

MLB rumors: Winter meetings preview - Five Red Sox moves to watch as offseason begins in earnest

The start of baseball's offseason has included some thank-the-lord movement, with a second-tier starter (Zack Wheeler) landing a $118 million deal from the Phillies and the hyperactive Rays dealing away a stalwart outfielder (Tommy Pham), much to the chagrin of ace Blake Snell.

With baseball's annual winter meetings beginning on Sunday at the Manchester Grand Hyatt in San Diego, all eyes will be on Chaim Bloom and the Red Sox, who have yet to make a major move, but will soon be on the clock.

So, what can we expect? Here are five areas of focus.


The Red Sox would be crazy not to consider deals for Betts if they believe he intends on reaching free agency, which he has made clear both publicly and privately over the last two years. They'd be crazier to give him away for nothing, however, and thus begins the dance of the offseason. The question they must answer is, "How much is too little?" and then draw a line in the warning-track sand. Potential trade partners like the White Sox and Braves have already spent aggressively, which means a Betts deal likely needs to happen sooner than later, since whomever acquires him must fit $28 million into their 2019 payroll and pretty soon that money will start disappearing. One team to watch: the Dodgers, who have money to spend, prospects to trade, and a World Series hill to climb after three straight near-misses.


Chris Sale just started throwing, per, and his five-year, $145 million extension kicks in on Opening Day. Selling low on the potentially dominant left-hander is a recipe for regret, especially since his contract could end up being pretty reasonable if he returns to health. The better trade candidate is Price, who turns 35 in August and has three years and $96 million remaining on a contract that's more likely to provide diminishing returns, but paradoxically includes fewer short-term questions. We laid out the case for Price being an actual trade asset on Thursday; as free agent pitchers leave the market, someone will be left short, and maybe Price becomes a target.


Trading Price may ease the financial crunch on a team hoping to drop below the $208 million luxury tax threshold, but it will blow another hole in a rotation that's already down one starter with the presumed departure of free agent Rick Porcello. The Red Sox obviously won't be in on Astros ace Gerrit Cole or Nationals World Series hero Stephen Strasburg. They also can't afford Madison Bumgarner or maybe even old friend Wade Miley. Will they go the opener route? Take a flier on a reclamation project like Felix Hernandez or Michael Wacha? Try to turn center fielder Jackie Bradley Jr. into a starter? Here's where Bloom's creativity will be put to the test.


Until he starts dealing, Bloom remains an enigma. He's beholden to no one on the roster, a position which allowed predecessor Dave Dombrowski to cut ties with Pablo Sandoval and Hanley Ramirez while they were still owed money. Could Bloom decide a roster overhaul is in order and use a supposed foundational piece like All-Star shortstop Xander Bogaerts or outfielder Andrew Benintendi to swing a larger deal? We may start to get some clarity on his thoughts next week.


At this time last year, the Red Sox were foolishly counting on 125 games out of second baseman Dustin Pedroia (he played six) and 162 out of a first base platoon of Mitch Moreland (91) and Steve Pearce (29). While some portion of either job could go to second-year slugger Michael Chavis, the Red Sox will be in the market for help at first and second, and this is a spot where Bloom helped unearth some legit finds in Tampa, from Carlos Pena to Logan Morrison to Ji-Man Choi. There should be no shortage of affordable options at first, in particular, from Justin Smoak to Travis Shaw to C.J. Cron.

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